Relationships

A Funny Way to Have Better Conversations

The Wonder Years

The last time I had dinner with my family, something strange happened…

Over Labor Day, I made a quick trip home, and on the first night back in Missouri, my family was unusually chatty during dinner. The Mom-pausing-mid-story-to-catch-her-breath-and-angsty-teenage-brother-chiming-in-with-anecdotes kind of chatty. Who were these people? This was not my family.

The next morning, I investigated.

My dad revealed that he’s started prepping for these types of get-togethers. “I’ve been writing down two to three conversation topics to bring up,” he said as he unfolded a miniature handwritten note he’d pulled from his trouser pocket. “They have to be positive; that’s for sure. They also have to be interesting enough that everyone will have input. And a question helps, of course. I’ll think of them throughout the day. It’s what I’ve learned from being a teacher for over 30 years, but I just realized I could apply this to our dinners. Otherwise…” He smirked and refolded the note.

For the rest of my week at home, every “casual” conversation pitched to our group worked with flying colors — and made me laugh. I was the only one who realized the sweet strategy behind them. But now that I’m back to my normal day-to-day in Brooklyn, I’ve been thinking about how his advice also works for other tricky situations — work events where I don’t know anyone, never-ending coffee shop lines and too quiet block parties.

If you’re looking for conversation starters for tough crowds, here are some ideas:

  • When asked what’s on his note this week, my dad said, “40% of Americans list ranch as their favorite salad dressing. This is a compelling subject for multiple reasons.”
  • Shared experiences (asking how they know the host, their thoughts on the beer being served, F trains delays)
  • Serial season three
  • Upcoming weekend plans or trips
  • Questions about their day (what they did, what they ate for lunch)
  • ANYTHING to just show you’re trying

    Recently I was reading this guide about how to be better at parties (as one does), and I came across this part: “Remember that conversation is part of what you bring to any social event. Ms. Fine [author of The Fine Art of Small Talk] said, ‘I don’t walk into a party without two to three things to talk about.’ These topics can be anything that’s interesting to you in the moment, and you need not even talk about them — but they are there if you need them.” Further proof that parents have most of life’s answers.

    Any other tips you have for getting conversations rolling? Any questions? A friend of mine has a rule with his mother that they won’t talk in the car on the way to a restaurant to make sure they won’t run out of things to discuss later, haha.

    P.S. A dinner party icebreaker, and funny questions to save the day.

    (Photo from The Wonder Years.)

    1. rachael says...

      I also agree with podcasts. there are soooo many and everyone loves them.

    2. Shannon says...

      I’ve started listening to a lot of random podcasts on my commute (I added to my collection from the reader comments on a recent post), and I’ve been surprised by how much it’s added to the conversations in my life. While visiting my family last weekend, I brought up that I finally learned the origin of the term “government cheese” from a podcast (Planet Money), and it turned into a hilarious and interesting talk. I would never have talked to my dad about his middle school lunches and 1970’s politics at the same time without this random conversation starter.

    3. I love this. I think so many of us forget about conversation when it comes to our own family. In a business or work sense we are always researching ways to network, but at home we forget everything!

      Your dad is a very smart man!

    4. Dana says...

      Well, I just love how positive and fun all of you are! It’s not always like this on the internet. I also love these suggestions.

    5. courtney says...

      I love the “Best American Science and Nature” annual essay collections, and while I’m reading them they always lead me to great conversations. They cover a variety of interesting topics, from ancestry tests to the way protected land is managed, to the way we taste things. But the science behind the relevant, everyday things we experience can spark great conversation (for example, according to one of the 2017 essays, wine tastes different depending upon whether you drink it with you dominant or non-dominant hand!).

    6. Erin says...

      Best conversation starter with any crowd of any age: “Is a hot dog a sandwich?”

      • Jess says...

        I just sent this to my siblings via text and a heated debate ensued. Pocketing this one for sure!

    7. I think it was Eleanor Roosevelt who said she’d just go through the alphabet, trying to think up subjects for each letter, as a way to get through a stiff dinner party with a non-talker as her table-mate. I love that. It makes me laugh just to think of what you’d come up with. Have you ever seen an anteater in person? Live?

      Love this post. :)
      Amy

    8. My roommates and I just hosted a party a weekend or two ago and it flopped completely. I think having conversation starters would have been great because then we could have interacted with our guests a lot more than just saying okay, help yourself and leave when you want.

    9. Kristina says...

      I’m not sure why, but I’ve found out that whenever I mention our robot vacuum cleaner (as one does) , it always make a great conversation topic and people get so excited and interested. Haha.

    10. I think that especially on parties the best way to start a conversation is by inquiring about the relationship to the host, as you mention in your article. That has sparked some interesting conversations for me in the past.

    11. Jess says...

      Conversation starter king in our family is my mum. I definetly haven’t inherited that from her. I remember when I was a kid, I was mostly emberessed by that that my mum could start talking with a strangers in a row, or on a bus or whenever… I was always pulling her by her sleeve – let’s go, mum! But now I understand how importamt this skill is, because now as an adult I feel a bit ousaider mostly in a work or at the parties, as I have difficulties with starting conversations about nothing just for fun and entertainment!

    12. Alli says...

      I definitely just made the mistake of having a 1.5 hour phone conversation with my
      Mom, days before I was supposed to go home for a visit. That was a total mistake! All the fun, interesting stories and general life updates that I would have loved to been in the room for during out chat we’re had over the phone and it wasn’t nearly as fun. Now I’ve instituted a details-only text policy for any communication directly prior to visits so that we can have time together to really share our lives with one another in person.

    13. I hate asking, “So what do you do?” So instead I like to ask, “Have you read any good books lately?” or “Made any good recipes lately?” or “Are you planning any projects around the house?” I could literally talk about all three subjects for hours and am genuinely interested in what someone has to say on these topics. Podcasts are another topic that’s often a winner and for the right person their favorite items at Trader Joe’s. If that lights someone up then I know I’ve really found a new friend.

      • Kayla says...

        I lived in an area with mostly SAHM’s and as a working mother, I found asking the tedious “What do you do?” to other mothers awkward (it may have been only awkward for me in my own insecurities that I might offend someone, but still). I finally learned to rephrase it as ‘So what keeps you busy during the day?’ which has opened up conversations in such a better way – I even find using this with people that I know are employed tend to answer differently, it focuses more on what they are literally doing all day versus the name of their occupation.

      • Joanna Goddard says...

        great idea, kayla.

    14. LV says...

      I don’t hate small talk! Some starters I’ll use at parties, dinners, in elevators…

      – What was the most delicious thing you ate today?
      – Was there any little delightful thing that happened today?
      – What are your top 3 super powers? (They don’t have to benefit society in any way).
      – Would you rather wear roller skates or ski gloves all the time?

      I also try never to ask people who just got back from traveling “how was your trip”? To me, that question is overwhelming. I’ll ask specifics, like “what was one thing you ate that you really liked?” and “was it different than you expected?” or “did you have any fun conversations with strangers?”

    15. Sarah says...

      Thank you so much. This was a a-ha moment for me. I struggle getting my son to talk about school each evening, and this would be a much improved approach.

    16. Katie says...

      Talk about the food at the party, or somehow work nachos into the conversation, as people tend to have strong feelings about them. Compliments can be good openers, but they’ve gotta be both sincere and specific. One of the best party chats I ever had began by me complimenting a guy on how much ice he had in his drink (like, jam-packed, which is just the way I like any cold drink, too).

    17. Anna Vitale says...

      This is brilliant! So helpful for business, too. I have many conference calls that start out with dead silence as I rack my brain trying to think of something to say (as a deep relationship person, small talk is NOT my strength and as a non-sports fan woman working primarily with men, am often out of the sports talk comfort zone). It never occurred to me to prepare in advance with a few fun, non confrontational ideas! Thank you, Stella!!

    18. Bren says...

      Yesterday I had groceries delivered to my house (with my screaming toddlers in the background) and this sweet girl who looked about my age, walked to my door with groceries and said “You look like you used to play volleyball or basketball!” with a big smile on her face. And I laughed because I actually did, but I think it was more of a, “tall girls unite!” moment and I thought about it all day because she was so friendly and kind and she totally didn’t have to be. We started talking for a while and she told me she had just moved to town and we exchanged numbers! But really just a lesson that it’s always a good idea to put yourself out there because I think most people always appreciate the effort, I know I did!

      • Danielle says...

        I love this! Being willing to be warm and comment on something when you”don’t have it” can be the start of so many great things. Whenever I hesitate I think of all the times someone has paid me a compliment or struck up a delightful conversation in an unexpected place. There are times when you are lonely or going through something and this random kindness and openness can truly make all the difference.
        Once i had just the best conversation in the customer service line at Staples and when I told my husband about it he said ” Maybe you’ve been working from home for too long”.

    19. Ro says...

      Haha, love the comment about not talking in the car on the way to the restaurant, so you don’t run out of things to say. This is so applicable to my life. I’m a big talker — I start word vomiting about my day the moment I lock eyes with someone. I can keep going once we get to our location, but often find myself repeating things. I’ve been trying to practice talking less and really making my words count. I want to tell good stories; the kind that people stop and listen to (a la Maya Angelou) and I feel I can’t do that if I don’t take a breath.

    20. Marci says...

      Ask any of the questions posed on this blog, especially those that generate lots of comments. :) My college-aged kids and I had a fun conversation about “simple pleasures” after I read a recent post. I now have some new ideas for stocking stuffers and care packages. They also found out ways to make me happy – and followed up with sweet acts of kindness.

      Another tip is to expand on topics that come up organically. When a fellow mom offered band-aids and bug spray from her purse, I asked other moms, “What do you have in your purse that you think no one else carries?” (I think that was a CoJ topic as well.) We all laughed a lot talking about that one.

      Or if someone dominates a discussion, I ask other people a related question so they can contribute…what are other favorite vacation spots, shows to watch on Netflix, traveling horror stories, etc.

      Other questions:
      * Worst first date – The *MOST* hilarious stories ensue.
      * First jobs/worst jobs – Who knew that there was a job determining the sex of insects?
      * If money (and talent) were no object, what would be your dream career? SO interesting to hear people’s secret desires.
      * Ask for advice – good family movies, gifts for in-laws, tooth fairy budget, etc. Almost everyone loves to offer their opinions.

      • Shira says...

        These are amazing tips, thank you Marci!

    21. Jessica says...

      My never-fail, go-to conversation starter: ASK FOR ADVICE, THEN LIE.

      “My husband and I are thinking of going on a trip next year; have you been anywhere you’d recommend?” “Oh really, Iowa?!” [WTF? Iowa?] “That sounds interesting! ” [No, it doesn’t. I’m not going to Iowa. I want to go to Iceland.] “What did you love about it? Do you have family there? What should we see if we go? Should we bring our kids?”

      Honestly, I’m not going to Iowa. But I’ve given the person an opportunity to talk about themselves and keep the conversation going. That’s your only goal.

      • Bren says...

        Hahaha this made me happy! I have totally done this!!!

      • Anna Vitale says...

        LOL’d reading this. So good.

      • jenn says...

        As someone from Iowa…its not so bad ;) (I would not come here for vaca, I, too would choose iceland!)

      • Jessica says...

        Hahaha Jenn, I was really worried about offending someone from Iowa! If it makes you feel better, I’m originally from Indiana. I don’t have a lot of room to talk! :)

    22. Tessa says...

      This is the best! In addition to your best reader comments section at the end of the week, could you add a conversation starter? I’m sure your introverted readers would most appreciate it!

      • Emily says...

        love this idea!

    23. alyce says...

      I have no idea how I found it, but I stumbled on Debra Fine’s CD recording of The Fine Art of Small Talk years ago, and the ideas she offers are absolutely golden. I still have it saved in iTunes and review the tips from time to time. I highly, highly recommend it to anyone trying to figure out how to better handle conversations in a wide range of social contexts. Friends once told me they always invite me to their parties because I can have conversations with, and keep conversations going with anyone. I attribute it entirely to things I learned from Debra Fine.

      • Shelby says...

        Looking it up now! Thank you!

    24. Sarah says...

      100% agree on velveeta shells v. Kraft! My husband disagrees w/me… and it has led to many entertaining conversations about mac and cheese.

    25. Natasha says...

      Oh my goodness I just had such heart-warming feelings towards your dad. That is so sweet that he does that! I can’t wait to try this out for myself too. As an introvert. I find I’m often trying to think of things to say and not wanting to bore people with my own life. But fun topics like people liking ranch is such a great approach! Thank you for sharing!

    26. I LOVE that “serial season 3” made the list! Made me chuckle :-)

      Rebecca

    27. Sally says...

      Back in August, my Mum and I were on an evening train from Paris to London. It was the last leg of our journey, which had started in Switzerland MUCH earlier that morning.
      Tragically, not far from the channel tunnel, there was a casualty on the train line and we had to stop. It was getting later and later into the evening, and people were getting tired.
      Then my Mum says quietly to me, “want to play a game?” so we start playing the alphabet game. That one where you pick a category (say, animals) and have to name one for each letter of the alphabet (aardvark, bear, cat, dog). Before we knew it, the people in the seats around us were joining in.
      After a few rounds, we were scouting for a new category, and Mum suggests “diseases and ailments”. Well, by this point it was pushing 3 in morning. People up and down the carriage are shouting out “Acne! Bubonic plague! Cough! Diarrhoea!!”
      The whole carriage are laughing (3am, hysterical laughing, but still!) and it made an awful, disturbing situation more bearable.

      • Jane says...

        I do this on long hikes with the kids!!
        Sports teams, athletes, tv shows, movies, cities, countries, boy names, girl names- every kid playing gets to choose a category.
        It also works when you have insomnia.

      • katie says...

        What an amazing story.

      • Amber says...

        Brilliant! Your Mum sounds cool :-)

    28. Cheryl says...

      The one rule I follow in any social setting:

      When talking with a good conversationalist, you leave the conversation thinking, “Wow, what a cool person.” With a great conversationalist, you leave the conversation feeling, “Wow, I’m a cool person!”

    29. Twinmommy says...

      I went on a LOT of blind dates in my single days. To break up the monotony, I had a few questions I would ask, not looking for a particular answer, but because I wanted to hear the thought process. An illuminating one was “What is your favorite subway stop?” If the guy looked at me like I was nuts, I knew right away he was not the one for me. I once told this to my mom’s best friend and I saw the light go on and the little cartoon bubble over her head “I get now why she’s still single!” For the record, my now-husband of almost 20 years had a great answer!

      • Hannah says...

        oh this made me laugh so hard, only because a) I am single and b) these are the types of things I would ask questions about… so pointless but the answers would be very telling xD

      • Shira says...

        This is hilarious and brilliant! Way to go!

      • Melanie says...

        Now I want to know what his answer was!

    30. Kelly says...

      One thing I like to ask at parties and when getting to know people is if they could pick any convention to go to (real or made up) what would they pick. Multiple answers are welcome. For some reason, I find that people have an easier time answering this question than the usual “what are your hobbies and interests?”. I’ve gotten some really fun answers!

    31. Ali says...

      We do a “top three” around our dinner table where each person tells us the top three things that happened in their day. I find out way more about our kids days than the standard “good” response that I used to get.

      • Shelby says...

        I love this! I think it also is better to ask for three things rather than just one, because instead of freezing and thinking about the single best part of your day, you can just start listing whatever comes to mind. I love to ask people about food, and I’m going to start using this and ask “what are your top 3 favorite meals” instead of trying to get people to think of their absolute single favorite. Thank you for the tip!

    32. Sarah says...

      My husband and I have been together 10 years and we have two kids. When we have a date night coming up, both of us write an “agenda” of things we want to talk about (saved to our phone notepads over a few days leading up to the date). Before, we would end up discussing our kids the whole dinner. Now, we both actively seek interesting things to talk about: articles, anecdotes, ideas, dreams for the future. It’s made us both feel like whole people again, and not “just” parents.

      • Shelby says...

        That’s so romantic! It sounds like it creates such a mindful mood – looking for things throughout your day you’d love to share with each other, and helping to build up to the date night. Great idea :)

    33. Agnes says...

      A girl on the street today asked me for $2 to buy her boyfriend some spoons. He had forks already, apparently. I told her he needed to get a job and she agreed – like, why are you buying him spoons?? But it was such a weird request that I gave her the $2. She told me that if she saw me around again (small town) she would buy me coffee. I feel like conversation just happens, and I usually talk about whatever pops into my head in the moment, which probably makes this the most unhelpful comment. (See???)

    34. I make a point to *not* text my husband throughout the day. Instead, I make a little list of things I want to tell him about in person later that evening. This is especially true if it’s something funny—I want to be there to hear him laugh!

      P.S. Stella, you were so friendly and easy to talk to at the Cup of Jo event last week!

    35. Colleen says...

      My son’s elementary school teacher took attendance every day by asking a question. Rather than saying “here” when their name was called, the students answered his question. Questions ranged from “Who is your favorite superhero?” to “Where do you wish you were right now?” to “Would you rather be really fast or really funny?” and everything in between. I so looked forward to picking him up everyday and asking about the question and his answer to it – it was a beautiful way to learn 180 new things about my son!

      • Mariana says...

        This is amazing! What a fun teacher :)

      • Stella Blackmon says...

        This brilliant! Thanks for sharing, Colleen! x

      • Ashley V says...

        I had a high school teacher who did this same thing. It was usually fun, but I’ll never forget the time he asked us who in the classroom we would want to date. Cue mortification for this shy girl!

    36. Erin says...

      I love this and it is especially sweet that your dad was so thoughtful about putting in the effort.

      Other commenters may have mentioned this, but for more ideas I highly recommend Tabletopics https://www.amazon.com/TableTopics-TT-0101-A-Original/dp/0975855603

      I use them at work for our monthly birthday potlucks (put anyone with a birthday that month in the hot seat!) , but have definitely brought the ideas for questions home. Really fun way to learn more about people (whether you know them well or not!) The seemingly simple questions usually lead to some really interesting stories or insights.

      • Lizzie says...

        What a wonderful tip! I think you just figured out Christmas gifts for every member of my family!

    37. Meghan says...

      I once heard my grandma talking on the phone with my aunt. My grandma asked seriously, “Now, what are you having for dinner tonight?” At the time, I thought it was a sweet but odd thing to inquire about. Now, I see that it is the stuff life is really made of. I now like to ask people about their dinner menu plans, and also this: “Take me through a typical day at work.” I love the podcast Forever 35 for the same reason – Doree and Kate ask each other things like, “Now how exactly do you take a shower?” These matters at first seem unimportant, but they’re what our lives are made of, and sharing them is oddly fascinating. Also, isn’t that what intimacy really is – sharing the everyday with another soul?

      • Stella Blackmon says...

        Love this comment so much, Meghan! And yes to the Forever35 questions <3

      • My mom, sister, and I share what we’re having for dinner several times a week over text, and definitely every time we talk on the phone! We used to have a daily email back and forth that started with what we had eaten the night before!

    38. Amanda says...

      Can your dad start a twitter or a blog and post his convo starters? As an introvert that has to schmooze at art events frequently with people I don’t have much in common with (no one watches Bravo!) I would love a constant source of back-up convo :)

      I also want to come to your family dinners, they sound amazing!

      • Elizabeth says...

        Agreed! I want to hear more!

      • Amy says...

        I second this, and I don’t even have Twitter (I’m a 31-year-old holdout)! I’d get Twitter for that.

      • Julie says...

        Yes yes yes I love this idea…please have your dad share more of his ideas! Loved reading this story Stella.

      • Sarah says...

        +1 to following Stella’s dad on Twitter! (Unfortunately, @stellasdad is already take, I just checked)

      • Stella Blackmon says...

        Laughing so, so much at this! LOL

    39. Mims says...

      This is topic came at a good time, because we are taking an acquaintance, who is recovering from a spinal cord injury to dinner. In her wheelchair. It is our first outing with her since the accident and bound to be awkward, so I am a little bit nervous. My brother died of ALS, so I am accustomed to handling wheelchairs in public, and talking to people who are differently abled. But until you take that first journey/conversation with someone new it is unknown territory. it helps to have Plan B in your pocket.

    40. Willow says...

      I love this question which generates really earnest thought and discussion… If you had to give up either cheese (in any form, e.g. on pizza) or alcohol for the rest of your life, which would you give up?

      • Marlena says...

        Oh god! It hurts to think about either scenario! This question would probably just send me into hysterics. haha

      • Christina says...

        Ha! That would be a conversation nonstarter for me since I’m both sober and vegan (I swear I’m not as insufferable or boring as I sound)… though people generally have strong opinions about those two topics.

      • jen says...

        easy. alcohol. I love cheese far too much. ;)
        love these suggestions as I’m hosting a dinner party of several couples whose only connection is knowing us! nice easy conversation starters.

      • T says...

        One for travel, if you could only ever holiday back to the same one place that you’ve already been to – or – instead go anywhere else every time but never ever return to your favourite place again, what would you choose?

        Sorry in advance for this next one. For when the night has descended into filth I have been known to ask good friends if they could choose any shape for their butt-hole, what would it be? Kids love this too. STAR! NO SPAGHETTI, NO GINGERBREADMAN!

    41. I love and am intrigued by this post and the salad dressing topic, made me laugh! I still love ranch or blue cheese dressing but am likely to order something a little lighter most of the time.

      I love the idea of planning conversation topics to get the ball rolling, but am a little intimidated about what those might be (although I’m kind’ve a talker so I usually don’t run out of things to ask about!).

    42. Lizzie says...

      Knowing how to talk, draw people out, and leave them feeling incrementally better about that moment in their day is one of the hardest and most undervalued things! I am often sent to conferences for work and when I first started my boss was astounded by the glowing reviews from others in the business, and especially clients. He asked what my trick was and I said “I never bring up work. ” Luckily he didn’t fire me : ) Especially at parties and conferences and weddings there’s a set routine of small talk (how do you know the bride and groom, what company do you work for, etc.). I find asking people about themselves in whimsical open ways such as what was the name of your childhood pet?If you won a trip anywhere tomorrow where would you go?! What is your favorite ride at a fair? Best museum you’ve ever been to? It leads them to open up a bit more and remember really fun things they might not have thought of in years! Plus, it’s always a fascinating and you end up laughing tons and it feels like you have an inside joke when you see them later and know that their favorite game is wack-a-mole and they once won a greased pig contest!

      • Rachel says...

        Love, love, love!!! What great questionsand such a thoughtful, meaningful reason for asking them.

    43. Since “How was school?” always gets the prescribed “Fine.” (yawn), my go-to dinnertime question for my kids is “Who got in trouble today?”. I used to worry it would feel too tattle-y or negative, but it has brought about great conversations on many levels. And you get a peek into their day-to-day lives.

      • Marlena says...

        That’s a good one, I’m going to add that to my go-to’s! My kids usually open up to the “What was the best (or funniest, or worst, or most awful and terrible) thing to happen today?” and that usually opens them up, at least my younger ones. The teenagers just roll their eyes and hmph. Riveting conversationalists, those teenagers.

    44. Marlena says...

      My sons love to randomly declare what their new “Entrance Songs” are (An entrance song being the song a WWE wrestler walks out to, usually something ominous or very loud and fast). One week it was Salvation by The Cranberries and the next it was a section of the musical score for Lord of the Rings. So, I guess my go-to conversation question to keep on hand should be “So, what’s your entrance song?” :)

    45. MollyCanada says...

      But…isn’t it okay to just be yourself and not have some rehearsed, prepared conversation topics to throw at people? Is it not okay to just accept your feelings of awkwardness if you feel awkward at a party? Sometimes parties can be a lot of energy in a room…and coming “prepared” could be a misfire. For instance, if someone came up to me at a party and started uneasily talking about ranch dressing, I would likely back away slowly…!

      Is it not enough to simply observe the room and organically strike up a conversation with someone who seems interesting to you, for whatever endless number of reasons people are simply interesting?

      Anyway, food for thought.

      • Louisa says...

        To me this is like saying “isn’t it okay for a hostess to just throw together dinner when guests arrive?” – in some scenarios a planned dinner would be overkill (let’s go to Chipotle, ‘kay?). But in other scenarios it’s nice to be prepared (keep a can of good salted nuts on hand; have a lasagna in the freezer; buy a case of ~$15 wine; always have ice cream + topping). In some social situations awkward pauses aren’t even awkward, and filling all the gaps is weird – but at other times it’s great to have a few go-to items up your sleeve.

      • Anna says...

        I can see where you’re coming from, tho also respect the idea of being prepared. I would prefer someone to let our conversation develop organically if it’s going to or perhaps move on to the next person if we’re getting nowhere. ‘Woyld you rather…’ etc. style rehearsed questions work well in a group but can make actually connecting with someone in any way harder. So I’d say it depends on the vibe of the party.

    46. Sarah says...

      This tip is from my mom, and it’s a good one: Ask couples how they met! The longer the couple has been together, the better it works. Asking this is almost like giving a little gift- the chance to relive finding their sweetheart!

      • Mims says...

        YES! this is my go-to question when i am meeting new couples. Very great conversation starter.

    47. Megan says...

      Ok. Small world, but I went to college with you and now teach in your dad’s department at the university. I love this story so much and get a good chuckle out of connecting this story to the guy who sends out mass emails about on-campus events and staff updates.

      Thanks for the giggle (and I am totally stealing this idea for my own family get-togethers).

    48. J. says...

      My dad always asks people: “where do you call home?” Everyone interprets the question differently, but it always ends up being an interesting discussion– where they grew up, where they lived prior to where they live currently, what they love about their neighborhood, how they consider more than one place home, where feels like ‘home’ to them, regardless of where they live. It’s an easy one! Carefully-phrased, carefully answered.

      • Dee says...

        This is a very good question. I love that you dont always associate it with the place where you grew up. It can mean many things to different people, I love that :)

      • I really love this question. It’s something I’m often curious about- having lived many places myself. But I do want to avoid the “but where are you from?” awfulness. Thanks to your dad for a thoughtful question!

      • This would be a great question because we live in a military community! I’d love to hear the answers. :)

    49. Jillian says...

      I kick off each and every one of my meetings at work, whether with clients or with my team, with a seemingly bizarre question. At first, people roll their eyes, but then they start to really look forward to what the question will be at the next meeting!

      Some examples:
      “If you could be a key on a computer keyboard, which would you be and why?”
      “What’s your favorite part of–or your favorite–body of water in the world and why?”
      “If you could design your dream bar or restaurant, what would its location & vibe be?”
      “What do you miss most from elementary school and why?”
      “What is the most unique holiday tradition your family has, and where did it come from?”

      We each go in a circle, and it ends up allowing the more introverted team members to share stories about themselves they might not have otherwise, and more than once has led to touching moments as people share childhood memories, tidbits and thoughts about people they love, and their own eccentricities. Allowing for vulnerability about something not related to work and showing your human side in an easy way has made it so much easier to be vulnerable and human about things at work.

      • Melanie says...

        That computer question is fascinating; I’m so curious as to whether people’s answers would align with introversion/extroversion. My immediate thought was “Well of course not one of the most commonly used keys. Who would want to be bugged like that all of the time? What’s the most out of the way key?”

        For the record, I’ve decided that my answer is the tilde,/swish-thingy key at the top left. It rarely gets used and the swish is pretty.

      • Denise says...

        The exclamation point! Because yes, I am enthusiastic! :-)

    50. Hilary A Tschoepe says...

      I can not thank you enough for posting a pic from The Wonder Years. Hands down best modern show from the 1980s.

    51. Jennifer says...

      That is quite possibly the most endearing Dad story ever.
      My husband and I starting doing a “Do you have your 5 questions?” review before dinner parties, having people over, visiting relatives etc. I believe the genesis was a visit with relatives not known for their expansive conversation skills. Now we do it all the time, and it’s a nice way to a) remember what we talked about last time, what events have happened for them and us since, and b) remind ourselves that good conversation is a skill to be prepared for and practiced.
      With some people it’s more like 25 questions, but it’s also useful to acknowledge that so at the very least, we come prepared.

      • Melissa says...

        I love this comment “good conversation is a skill to be prepared for and practiced”. It’s also a good way to put aside your own feelings of being uneasy to help the conversation be more comfortable for everyone.

    52. Meredith says...

      Lovely! I *HATE* the “got any plans this evening?” go-to of checkout persons everywhere. It’s Tuesday night at 7PM and I’m at Whole Foods; I’m not heading to a rager afterwards.

      • Joanna Goddard says...

        hahahaha

      • Danielle says...

        Hahahaha YES!

      • Amanda says...

        Hahaha, my hairstylist always asks me that and I have to inform her each time that I am going straight home to put on my pj’s and watch tv. I’m a waste of a blow out :)

      • Emily says...

        Hahaha YES I so relate to this. Glad I’m not the only one. :)

    53. I’m getting anxiety reading all of these go-to questions when people say “EVERYONE HAS AN ANSWER!” I don’t have an answer for all of them! I did learn that my karaoke song is not the same as my batting song (even though I don’t know what my batting song would be), and I need to think long and hard about my favorite Michael Jackson song, among other things. I guess it’s time for some serious introspection! Haha.

      • Claire says...

        Just make something up.

      • n says...

        Haha – maybe you a different article to the one Caroline pointed… maybe this: https://www.nytimes.com/2015/12/06/opinion/a-neurotics-guide-to-small-talk.html
        ;P
        I like to repeat these two mantras:
        “Everybody is doing the best they can” – from Brene Brown’s excellent chapter that is now available for free!! Can’t recommend it enough!!
        https://brenebrown.com/downloads/
        and the second one from Neil Gaiman:
        ““Everybody has a secret world inside of them. I mean everybody. All of the people in the whole world, I mean everybody — no matter how dull and boring they are on the outside. Inside them they’ve all got unimaginable, magnificent, wonderful, stupid, amazing worlds… Not just one world. Hundreds of them. Thousands, maybe.”

    54. Virginia says...

      I love this post! I have two thoughts:

      One: can you share more of your dad’s conversation topics!? I’m so curious!!!

      Two: at my work, we do a weekly “hot seat”: 5 minutes of ask-anything for one team member, and people come up with the best questions: “If you could be any kitchen appliance, what would you be?” “Would you rather be secretary of state or a Supreme Court justice?” “What’s your favorite family vacation you’ve ever taken?” “Best gift you’ve given?”…and I find that I ask better questions when it’s in a quick setting like that. Which has inspired me to repurpose them for future settings!

      • Joanna Goddard says...

        the hot seat is such a fun idea for a workplace. i love that.

      • Sherry says...

        Yes! We need a “Questions my Dad asks” follow up every once in a while. Just like Joanna’s Toby and Anton in conversation posts.

      • Jac says...

        This would be a good Cup of Jo Friday weekly post- one random question without any explanation. “Would you rather be secretary of state or a Supreme Court justice?”

        A SCJ obviously! I would be drunk with power. Like Jafar from Aladdin.

      • Claire says...

        Wow, I have never laughed so much in a comments section in my life. CoJ’s readers are the best!

      • Agreed, Sherry!

    55. Maria Luisa says...

      For my dinner out tonight I think I’ll talk about your father strategy

      • Joanna Goddard says...

        hahahaha good point! same :)

    56. Emily says...

      I’m a born question-asker. In fact, I sometimes have to hold myself back b/c it can freak people out. My husband and his friend used to call me Miles Russell from Uncle Buck.

      I will say, I never lack something to talk about and can always find myself in the center of fun conversations at parties. I also make friends very easily b/c people DO enjoy talking about themselves. Maybe it’s a Scorpio thing, I don’t know. But I am so curious about people!

      My challenge now in raising a pre-teenager is finding ways to encourage and inspire conversation that HE brings about. To this end, we do the peaks and pits or the high/low. We’ve started to incorporate the “middle” to this part of our conversations. It’s a great way to enjoy a meal together and a fun way to learn about him, his friends when they’re over, and also the facets of my husband’s day. If you don’t know peak and pit-you name the peak of your day and the pit.

      • Jenn says...

        OMG I’m a Scorpio too and a total “Miles Russell”! :)

        Sometimes I feel like my questions come off as an interrogation (especially when talking to my daughter’s boyfriends) but I’m honestly just intrigued by people and fascinated by behaviors.

      • Frances Smith says...

        ME!!!

      • KL says...

        We do something similar—high, low, surprise. The surprises are often fun. We also sometime ask Rose, Bud, Thorn (rose and thorn are high and low). Bud is something you’re looking forward to. As for bringing kids into the conversation with other adults (big events can be so awkward for kids), I like to ask the adult if they remember something about a milestone my child just went through. “When did you get your ears pierced?” “What do you remember about 3rd grade?” “Did you play an instrument as a kid?” It’s fun to hear people talk about their childhoods.

    57. Maia says...

      I love this! I seriously loathe “how was your day?” It’s too broad and unwieldy. What part of my day? Breakfast? Dinner? Unless it’s a rare, amazing day, most are pretty ordinary.

    58. Claire says...

      My mother, who is 87, shows up to family dinners with a handwritten list of jokes that she got off of the internet. She does it mainly to entertain the grandkids, and it works, and often puts them, and everyone, at ease and gets them chatting. And the adults always get a laugh too.

      For myself, I sort of keep a list of little stories and topics in my head to bring up, but also I try to remember to take an interest in others, and ask questions during a conversation. Sometimes just a simple “tell me more about that” will get the ball rolling.
      (btw- looking forward to season 3 of Serial, but also I just listened to episode 1 of a podcast called “Last Seen”, investigating the 1990 art heist from the Isabella Stewart Gardner Museum in Boston. I am hooked!!).

      • Amy says...

        Your mom is so cute! I love that.
        Downloading ‘Last Seen’ right now. Thanks!

    59. This is silly but I often am unintentionally conversational in elevators almost anywhere if I’m carrying the right thing. One day, I had my leftover coffee in my Superwoman mug, which gets comments from ladies of all ages. Another day, I had water in a pretty 25oz Swell bottle (fun fact: it can hold a whole bottle of wine for incognito drinking in the park). My hubs gave me a tote that has the Golden Girls on it with the lettering “The Real Housewives of Miami.” I guess carrying fun everyday objects is a good conversation starter? And if my toddler is with me, she handles all socializing for me. I’m a struggling introvert so I’m grateful!

      • Claire says...

        Oh my gosh, you are on to something here. My husband drives me crazy because he likes to wear band t-shirts everywhere he goes, especially metal bands, or Rush t-shirts. I’m like “for crying out loud you are a grown up – can you not just sometimes wear a simple polo shirt?”
        But no kidding – it is like some kind of a secret club and the t-shirts are how they identify each other. He makes so many friends from wearing them. Random strangers will spot him, and come up to him (DUDE! COOL RUSH SHIRT!!) and start long involved conversations about the band, tour dates, albums, song lyrics, and they go on and on, and bond over it all. Meanwhile I am standing right next to him and it’s like I’m invisible. And I’m out in the world, I’ve got things to say, but this never happens to me. Until I bought a Studio Ghibli t-shirt and then one day at the grocery store I was suddenly the most popular shopper ever, and people kept stopping me saying I LOVE YOUR TSHIRT!!! and the barista at the coffee bar gave me a free chai.

      • Joanna Goddard says...

        oh my gosh YES! my old roommate was a cellist and she would meet EVERYONE everywhere she went because it was such an instant conversation starter. it was fascinating to take the train with her.

      • Mims says...

        My husband is an inveterate T-shirt wearer. No kidding, we were just at a Gomez concert and he wore his Death and Taxes Moonlight Brewing T-shirt and he got stopped 3 times by strangers to talk about that beer and a high five from the bartender. Me, I would rather not be a walking billboard, even for products I like!

    60. Jenna says...

      Before we were dating my now-husband would tell people “if you are nervous about having to do small talk at a party bring Jenna and she’ll take care of it all for you.”

      Lull’s in conversation freak me out so I can’t help but ask tons of questions, beginning with “tell me how you spend your time” and typically ending up with something very random ask I grasp for content starters. I think it’s important to remember how enjoyable it is to be asked a question…any question!…and to have your response listened to attentively. Thus we should never feel awkward or weird about asking other people their thoughts if we are happy to listen and respond to their answers!

    61. Anna says...

      When I was a camp counselor, one of the questions I would ask my table at meals was, “where have you been in the shoes you have on?” This question elicits some great stories -even from kids- and it helped me learn that it’s sometimes better to tell the more interesting version of a story, rather than the most accurate one ; )

      • Fran says...

        Ooo I like this one!

      • Nandini says...

        I love love love this one because it’s what I always think about when putting on my shoes! Didn’t know other people thought of it this way.

        If I can share, my favorite pair are sturdy rubber boots bought for $10 last minute in Ecuador to hike in. They are impossible to get clean at this point, and every time I put them on I look at them and think, ‘these boots have Amazonian mud, Atlantic ocean salt, and the red mud of my college campus on them.’ And it makes me so happy to wear them.

        If anyone else wants to share their answers to this one I would love to hear!

    62. Kate says...

      Love this idea! And Serial Season 3… I don’t think I could be any more excited! I live in Cleveland, and I’m organizing a Serial meet-up discussion group of mostly casual twitter acquaintances, so you know it’s gonna be a good conversation!

    63. Giselle says...

      Omg serial season 3 is here?! 🤯🤯

      Love this post, going to try it with my husband!

    64. Two great conversation starter questions – what was your first job? what was your shortest job (i.e. – how quickly did you quit or get fired)? Both bring up good laughs and lead to great conversation.

    65. Emily says...

      Love the advice to arrive at a party with conversation topics in mind! I’ve been trying to do the same for phone dates with long-distance friends. It’s so hard to get these things scheduled, there’s no time for awkward pauses!

      On a related note… lately I’ve started working on a cheat sheet for keeping up with old friends. I have a truly terrible memory, and I hate how it holds me back from really being a good friend. If we don’t talk often, I’m going to forget even the most basic/important elements of your life, and until the cheat sheet I thought there was nothing I could do about it. (For example, during a recent phone date with months of life to catch up on, it was only because of her phrasing that I could tell she had previously told me her grandma has cancer. This felt like brand new information to me, but if I had reacted that way she would very rightfully have been hurt.)

      So I’ve started a note in my phone where I list pertinent details after catching up with friends. If anyone ever saw it I’d be absolutely mortified, but it’s sadly necessary. Here’s an example, names have been changed…

      Kayla:
      – brother (Andrew) alcoholic, doing well as of Sept ’18, 3 kids
      – may be up for promotion soon
      Nora:
      – due in February, has a hunch it’s a girl
      – visiting Rachel in October
      – grandma has cancer

      ANYWAY. Just thought I’d share in case anyone else has a brain like a sieve and doesn’t want their friends to think they don’t care.

      • Olea says...

        This is a really great idea! Thanks for sharing.

      • Sam says...

        I do this too! And I’ll put reminders on my phone calendar “Call Jamie, has appointment with oncologist today.” There is no way I can remember all the details without reminders and my friends and relatives are so appreciative that I reach out. I guess it doesn’t really matter how I remember if the end result is that I do and my loved ones feel loved and supported!

      • Katrin says...

        Hahaha! Actually, this is a really good idea for friends living far away that you only talk to a few times a year! I might steal it;-).

      • claire says...

        Emily thanks for this! could be a great anxiety reducer for me and would never have thought of it.

      • Joanna Goddard says...

        this is a really beautiful idea, emily.

      • Natalie says...

        I do this too! Also – genius for networking. ‘Remembering’ details about people impresses them, makes them feel important, and keeps you from second guessing them/avoiding bringing up names and topics you’re not 100% sure you remember correctly.

      • Elizabeth says...

        This is such a nice idea. So kind of you. I try to put doctor’s appts, etc on calendar, but this is a great addition. Thank you!

      • Lauren says...

        I’ve started doing this as well in the “notes” field in each friend’s contact in my phone. I recently found my mom’s cheat sheet for my sister and me and initially thought it was bizarrely hilarious, but came to realize it was genius. What prompted me to finally start keeping notes on my good friends was having so many close friends in the medical field, at various stages of residency and fellowships, and constantly forgetting where they were in the process, what they were (or were considering) specializing in, when the next chapter would start, when each mini-graduation was. I started to feel so ANNOYED with myself because I knew I was causing them to repeat themselves and was also embarrassed when someone else would ask me what so-and-so was up to, and I could only offer a vague summary. Taking notes has helped a LOT.

      • Kate says...

        When I started dating my current boyfriend, I created a note in my phone and I would update it after every date: the name of his mom and his sister, his undergrad, the minor league hockey team he played on after college, the name of his phd advisor, the names of his mom’s dogs, his best friend and where he lived, etc. It just felt really important to remember these things, but it also felt a little stalkery and creepy to be keeping notes. But, it did help me remember, and I think our bond was stronger because I was able to remember these important details. We’re still going strong a year and a half later, so it seems like past me knew what was up :)

    66. Brandy says...

      I have found myself doing this exact thing with a new friendship that is blossoming. I’m not one to enjoy moments of long silence as I instantly get nervous! So to avoid these moments, I “prepare” for our lunch dates by thinking of a few subjects to talk about or questions to ask. I find myself being much more relaxed in the moment when I take some time to prepare:) I try to recall a few things we talked about during our last lunch date so I can ask how that event went or how something ended up!

    67. Rachel says...

      Rather than the perennial “how was your day?” I like to ask “what was the BEST thing that happened today?” It helps frame the conversation in a positive light, and forces your conversational partner to think back on the little good moments, even if it was tough or boring day overall.

      • love this, stealing it!

    68. shade says...

      As a teen, I used to jot down topic ideas for a phone chat with a boy. Even if I didn’t use them, it made me feel easier about that first hello.

    69. Sara says...

      On our first couple’s weekend trip while dating, we were at a romantic dinner in Balboa Park. I was so nervous we would run out of topics, I pulled out a travel sized “table topics”. He did tease me a little but we really had some great conversations. My family still teases me mercilessly;) Married three years with a 16 month old and one on the way-guess it worked;)

    70. diana k. says...

      It takes a lot for me to get out of my head at crowded functions enough to have fun, so I usually have to employ some social strategies. Here are a few that have worked for me over the years.

      -Ask people what their go-to karaoke song is. Music talk can take you pretty far.

      -Ask people what their name means or if they were named after anyone. I always ask about people’s middle names because I don’t have one. If you find yourself chatting with someone, you can both guess the names of other people at the party/event. This frequently turns into creating elaborate backstories for people you don’t know.

      -Insist that Tom Cruise peaked in the 80’s and ask everyone I meet what their favorite Tom Cruise movie is in an attempt to prove my point.

      -Ask someone what type of booze gave them their first bad drinking experience- most people never go back to that drink and almost always want to talk about it.

      -If it is at all available to you, dance. Socializing on a dance floor is actually way less awkward than when standing still.

      -Ask someone what their “Plan B” career would be.

      -Ask someone what magazines they buy at the airport/subscribe to. I love magazines.

      I’m also open to any others!

      • Johanna says...

        These are so great!

      • Stella Blackmon says...

        Love these Diana! The karaoke song question is hilarious and perfect. Thank you for sharing!!!

      • Steph says...

        These are all great questions — how do you use them? Do you start off a conversation with them, or work them in? Would you discuss Tom Cruise with a stranger? How would that come up? Geez, I am really bad at this!

      • Claire says...

        I like to ask about all time favorite movies. And just recently, before launching into some thoughts about potatoes, I asked the other people at the table with me (husband, BIL and SIL) if they thought we talked about food too much. This was an unexpectedly inspiring question- everyone had an opinion, if you can believe that, and they began to talk animatedly about why you could never talk too much about food, and recipes that had caught their eye, restaurants, etc. It caught me by surprise. in fact I don’t remember now if I ever got around to the potato story….

      • Libbie says...

        Steph, I struggle with that too, but I’ve found a tactic that works for me. I’ll preface my question/conversation starter by saying where I first heard the topic from.

        For example, “The other day a work, we were talking about everyone’s first concerts and one coworker’s was Backstreet Boys! How awesome would that be? What was yours?” OR “On the radio on my way home, the hosts were talking about condiment choices. Did you know 40% of Americans prefer ranch dressing?!” OR “I was listening to a podcast about X and it made me think about how Tom Cruise hasn’t had a good movie since the 80s”

        It can help make it feel more natural. You’re telling them about a conversation you already had/heard and want to hear their opinion, too.

      • Diana K. says...

        Music is easy cause it’s usually playing, so you could comment on it, like “I like this song, but it’s just way out of my range” and lead into the Karaoke thing. Maybe you hate karaoke, lead with that. You’re looking for a karaoke song that’s not embarrassing, and asking for tips. Booze is easy cause people are drinking it. Talk about a strange drink combo you heard about. “I never understood any liquor mixed with grapefruit juice.” Selfishly, these are all things I’m sort of interested in and curious about so I usually phrase it with “I have a theory about middle names” or “I’ve been trying to get my friends to watch the movie ‘cocktail’….” Of course sometimes the topics bomb and you just end up as that Tom Cruise psycho for the night.

      • Jo says...

        Diana – “Of course sometimes the topics bomb and you just end up as that Tom Cruise psycho for the night.”
        omg – I laughed hard at this line.. imagine being remembered by an acquaintance as a TC psycho..hahaha

    71. LH says...

      One of the ways I feel loved is when people ask me good questions and I love to ask other people intentional questions as well. I noticed when I’m with my dad (I’m 34) he asks me very factual questions like “did your plane leave on time?” and those always leave me feeling a little sad and grasping for a response that inspires conversation. I’m dying for him to ask me how I feel about something (anything) – he could just ask me “how did you feel traveling today?” and I’d feel cared for, like my feelings matter, AND I’m sure I’d talk nonstop.

      (BTW I have shared this with my dad and he was very receptive, I think he just doesn’t always remember <3)

      • Christina says...

        LH – your feelings definitely matter to your dad! Most dads are just terrible at conversation, I’m beginning to realize. Your comment made me think of this funny piece – which Stella posted a few weeks ago on the Friday links, so you may have seen it already. <3 http://reductress.com/post/what-else-is-new-dad-asks-a-third-time-stretching/

      • diana k. says...

        Yea wtf dads. I go out to eat with my dad and he goes on and on about property taxes. He MIGHT get a “how’s work” in there, but usually not. :/ I have to remember to love him for who he is.

      • Kat says...

        This is such a good point!! My in-laws are sweet people but very emotionally disengaged. I have really struggled with how to pin down what feels so hard about building a good relationship with them, but it’s this! Their conversation topics are always logistics or scheduling related – do you think there will be traffic? how is the weather? how do you think the weather will be where we’re going? what kind of wine should we have? – it drives me crazy because it’s like they’re trying to have a conversation, but not really engaging. Love all the tips in this thread!

      • Danielle says...

        Dads are so tough! Also I don’t know anything about your background but I come from a blue collar midwestern family and conversation is tough! We went home for Christmas for the first time in many years and the number of times we answered “Which way did you drive?” so many times. This scene really hits home: https://www.youtube.com/watch?v=_8ArgiWUcg4

      • Rowan says...

        My father never asks me anything, yet will talk to my three siblings (and I am the one who gave birth to his only grandchildren). Over the summer he angrily told me I’m stupid. Some fathers actually don’t care about their child’s feelings.

    72. Erin W says...

      Interesting travel stories are one thing that gets almost everyone talking—
      From delayed flights with overnights in the airport to public transit buses with chickens and 50 people crammed in to getting lost and not speaking the local language or waking up to go to the bathroom in the middle of the night and seeing a wild elephant (actually happened to me haha)

      These kind of stories usually have everyone laughing, commiserating, and/or chiming in with their own stories!

    73. Amanda says...

      When asked what’s on his note this week, my dad said, “40% of Americans list ranch as their favorite salad dressing. This is a compelling subject for multiple reasons.”

      I love this.

      • Stella Blackmon says...

        Amanda, haha <3

      • Kat says...

        This is exactly how a dad would say this. so good.

    74. I’m one of those weirdos who don’t find small talk to be a problem. I don’t love doing it, but at least I know how to go about it. Some of my go-to’s are asking about any travel plans (or recent travels). Even if they just went up North to visit their parents, there’s a story there.

      Also, MOST people are super into TV right now (there’s something for everyone!) and if you ask what they’ve been watching lately, 9 times out of 10 they’ll have a show they’re dying to talk about!

      If the other person is a mother (or an involved dad, as most of my peers are), all I have to do is ask about their kids and we have plenty to talk about!

      The biggest thing is to just keep asking questions. People love to talk about themselves. :)

    75. Kristina says...

      This is one reason I listen to This American Life, ha! Honestly, I love the program so much and would listen to it no matter what, but truly, each episode offers some kind of anecdote or point to ponder that I want to share with someone else.

      I love to travel and always have some place that I’m daydreaming about so I usually ask if they have been somewhere recently or if they have any travel plans in the future. It’s usually a good way to get conversation flowing!

      • Stella Blackmon says...

        Yes, Kristina! Always feel that way about TAL. Every single episode I feel like I have to tell at least one person about it, haha. xx

    76. Ha! As a former online dating coach, I often had to help my clients come up with questions/answers/topics that steered them away from just interrogating dates about their dating profiles or their intentions to settle down/get married/have kids/whatever. That stuff is important info to evaluate in a romantic prospect, yes, but diving into that shit on Date One generally doesn’t produce a vibe that allows you to connect and even see whether you’d like to go on another date or kiss this person, let alone settle down FOR-E-VER style.

      Often my advice would trend around what pop culture and hobbies that people consume–stuff that’s streaming on Netflix, why you enjoy or dislike a certain board game mechanic, why you aren’t a fan of the big comic franchise movies that lots of people seem to love. I’d also do some social media talk–how you balance your Twitter personality vs. your workplace personality, the pressure to have “perfect” pictures on Instagram and how it might slow you down from posting as much as certain friends do, what other “old school” networks you were on before your current iteration.

      And of course, work, but often not the meat and potatoes of the job itself. More like the inter-personal dynamics. Who is annoying and who is delightful at the office, are there morale events that help you connect, who’s the “bad apple” attitude (including admitting when it’s you and talking about why). This could get tricky with clients who were unemployed or self employed, but sometimes talking about the little trivial things in a workplace that you oddly miss (that one “don’t reply all” email thread where everyone keeps replying all telling others to stop replying all… that’s a common one in bigger companies) etc.

      Basically, I’d guide people to talking about stuff that tended to showcase how people’s taste and minds and personalities worked and how they related to other people. That’s the kind of thing that lets you really connect if it’s going to happen, and gives you a decent slice of what they’re actually like without it feeling like an interview.

    77. Joan says...

      “A friend of mine has a rule with his mother that they won’t talk in the car on the way to a restaurant to make sure they wouldn’t run out of things to discuss later, haha.”

      Haha, I often find myself doing the same when writing emails to friends – I’ll write a whole paragraph then delete it, thinking it’d be more fun to save for over drinks when I see them later that week.

    78. Ashley E says...

      I’m a talker in general, but my go to to REALLY get to know a group is “what is your batting song?”- You know in baseball, when they get announced and walk to the plate and have ‘their’ song they picked to pump them up. EVERYONE has a song… it’s a gem of a question and opens up so many more conversations!

    79. Lynn says...

      This makes me think of a Dorothy Parker story called “Too Bad”. A husband and wife are getting a divorce and then you learn they can’t (she) or won’t (he) talk to each other at the end of the day. They can talk to others, but to each other they just flail. So much is unsaid, it’s infuriating! It makes you really think about partnership, friendship, and family as relationships that require nurture and effort sometimes.

      Side note, I think it was on COJ a while back, I read a comment from a woman who travels for work and writes down little things throughout the day so that her nightly phone call with her husband has more going on, instead of a simple, “I’m so tired, how are you?” I do this now too!

    80. Cindy says...

      At the dinner table, we routinely begin with, “Talk me through your day.”

      If I’m in a conversation with friends/acquaintances, I almost always start with, “What did your week look like?”

      • Stella Blackmon says...

        “Talk me through your day.” Awww, Cindy! Love.

    81. Gail, in northern California says...

      I don’t know my sister-in-law that well and thought, “Oh dear, the hour drive to the coast is going to be sheer agony.” I took the time to go back through the archives of this blog and typed up some questions and told her exactly what I proposed to do, adding “At any time, you can say ‘That’s none of your business!'” Along the lines of “what was your first job?”, “what was your favorite job?” and “if you could design the perfect job for yourself, what would it be?”—it eased the tension and I actually learned a lot about my sister-in-law. She humored me and was good-natured about it too. We had a good laugh during the return ride home when I threw out this one: “What was your best kiss ever?” She laughed and said, “That’s none of your business!”

    82. Jane says...

      Your dad saying “this is compelling for multiple reasons” about ranch made me laugh out loud and I want to know all of his reasons!! Haha what a sweet gesture for your family and I can’t wait to try this out…especially with all of the holiday parties right around the corner :)

    83. selby says...

      i’m a “program manager” (basically a project manager) at work and i hold 4-6 meetings per day with different cross functional teams. i usually try to have a casual conversation before the meeting starts (to allow everyone to get there on time and build camaraderie with the teams).

      the most popular (and now requested) is zodiac quizzes. before the meeting i’ll find a zodiac quiz to find what type of bagel they should order, shoes they should buy, tv show they should watch, olympic sport they’d be (both winter and summer), spirit animal, etc. based on their sign. this forces everyone to participate and respond if they agree or disagree. it’s a hit!

    84. Rebekah says...

      I think initiating energetic, self-sustaining conversation depends so much on being able to read the other person and actually being curious about their answers.

      • Stella Blackmon says...

        Totally agree!! x

    85. Erica says...

      Solid advice :)

    86. Sarah says...

      I absolutely love this! I get irrationally upset when we invite people over and they don’t have anything to talk about other than themselves, so I love that advice that “conversation is what you bring to a social event”. My go-to line that I learned from the Happier podcast is “what’s keeping you busy these days?” It’s an open ended question, and leaves people free to talk about a tv or podcast binge, a new hobby, a trip….pretty much anything! And then it can start a nice dialogue.

    87. ooomg i love your dad so much. “They have to be positive; that’s for sure.”

    88. Jenna says...

      This is so great! I recently read a blog that pointed out the importance of greeting people with an “Oh there you are!” attitude instead of a “Here I am!” attitude. The primary difference is asking questions about them instead of immediately talking about yourself. Of course, conversation is a give and take of both, but showing that your first concern is to hear about them (especially if they are they are the guest, you are initiating, etc.) is warmly endearing.

      I’ve also noticed that I have a few people in my life who loveeee to talk about themselves and have a hard time allowing the conversation to land or stay on anyone else they’re talking to. I have let go of a lot of frustration since I’ve readjusted my expectations and realized that the time I spend talking to them isn’t the time to talk about me (I have other people in my life that I can talk to about myself!). However, a handy little trick I’ve learned when I get the bug to talk about myself in these conversations is to ask questions of them that I also have a response to.. Their bewilderment that someone else could have a shared experience with them is always priceless!

    89. Heather says...

      I always like to ask – if you could eat/drink only 3 things for the rest of your life, and health is not a concern, what would they be?

      (Ex. Mine are mac and cheese, oreos, and beer. I am a real sophisticate.)

      The conversation leads to SO many other conversation avenues and debates – how you were brought up, meals you’ve had in your travels, are velveeta shells better than Kraft (yes), is saying “tacos” or “pasta” too broad?

      • Joha says...

        Oooh. I’d be so tempted to say ‘soup’, ‘salad’ and ‘cookies’.

        But admittedly that leaves me a LOT of wiggle room.

      • Heather says...

        Hah yes Joha, that answer would be rejected!

    90. Quinn says...

      Can I just say that the photo choice for this post made me smile? :) Hooray for the Wonder Years!

    91. Family dinners can be hard, especially when the kids are young. We ask three questions at the end of the day: “What was the most interesting part of your day?” “What was the hardest part?” and “What was the funniest thing that happened today?” It’s taught my kids to stick around the table for the conversation.

    92. Jamie says...

      I can remember doing this in 8th and 9th grade when on the phone with boys whom I liked. It was during cord-phone times, so I would sit in our home-office swivel chair and like, casually, bring up “baseball” and other topics I’d prepared. LOL

    93. I just love the photo you’ve used at the top… I have very fond memories of watching The Wonder Years every Wednesday night with my dad. :)

    94. Rachael says...

      We do something semi-similar with our kids: we go around the table and everyone shares something good from their day, something bad from their day, and an act of service they did for someone else.

    95. Your dad is awesome! But sorry, I loathe the question: Upcoming weekend plans? It’s over-used by bank tellers and other strangers who have no business knowing your weekend plans.

    96. Kimmie says...

      My go to question is “What is your favorite Michael Jackson song & why?” I still have yet to meet anyone who doesn’t have one and most of the time, it stirs up a conversation about a memory they have tied to it and then launches into other topics. Sounds silly, but it works for me!

      • Kari T. says...

        I’ve actually tried this conversation before and my SIL actually said “I hate Michael Jackson”, well then guess that’s the end of that topic lol.

    97. Caroline says...

      The best convos start with a “yes and” mentality. If a fun topic comes up, really dive in and commit. My favorite story includes a group of friends eating Pub Mix (https://www.costco.com/Utz-Original-Pub-Mix%2C-44-oz..product.100113277.html) and started casually talking about which snack item was the best. This proceeded into a full night of Pub Mix tournament with rounds of competitions until we ranked each one with a final winner (Rye chips FTW!!).

    98. Andrea says...

      At Christmas, I resorted to putting open ended questions on pieces of paper in plastic Easter eggs. Then, before and during dinner, each person chose an egg and answered first. Each person was expected to answer the question (like where would you travel if money were no object), but could pass once.

      This structure worked because the group was disparate (hosting at my mom’s with neighbors as guests) and because of the family tension we have. It allowed each person to weigh in and tell a story and to give us common ground.

      A bit of a desperate measure, but it worked like a charm.

    99. Caitlyn says...

      Love this! Suspect that I would thoroughly enjoy discussing ranch dressing with your dad.

    100. Nina says...

      This made me think of David Sedaris’ skit 6-8 Black Men that I listen to every Christmas or whenever I need a good laugh. In it he talks about the random questions he’ll ask people/taxi drivers – what does a dog say in your language. He found out that a blind person can get a gun permit in Minnesota or maybe it was Michigan.

      My son and I often play “Would you rather” probably based on Joanna’s recommendation.

      I also love to use the phrase “Tell me more about that” as I was so thrilled when someone said that to me once.

      My big issue, especially in this politically emotional time, is how NOT to respond negatively or even show my shocked outrage when people say ridiculous things like “Oh the economy is SOOO much better now with 45 since Obama tried to make us all poor.” I resorted to shouting FAKE NEWS when I provided ACTUAL FACTS on the US deficit and jobs lost and taxes, etc until the perpetrators said “I’m not going to argue” and walked away. I had originally resorted to telling my 10 year old (who won’t let us say 45’s name in our house) to just ignore the people but when they started saying FAKE THINGS about Obama…I had to speak up.

      • Claire says...

        I love “6 to 8 Black Men”! Even though I’ve heard it a million times it always makes me laugh.

    101. kate says...

      “What was your first AIM screen name, and why?” (SO embarrassing and hilarious.)

      • Carrie says...

        Ahh AIM! I love this question! One of mine was CleverLilMonkey. Man I used to LOVE crafting perfectly hilarious away messages

      • alycia says...

        OMG! This is both hilarious and frightening.

      • Stella Blackmon says...

        Laughing so much, Kate!

      • diana k. says...

        cookiejuice90 WHO KNOWS WHY!

    102. Megan says...

      The last two ideas seem pretty standard but I totally love that your dad put effort into this. So cute! I used to have a secret sheet in my purse for first dates when I was so afraid I would run out of things to talk about. It definitely eased a lot of my jitters. :)

    103. Kaye says...

      “something strange happened,” I thought for a second Joanna wrote this one—ha!

    104. Ay says...

      Intriguing! Love this.

    105. Jessica says...

      I feel like we really need the specifics here. What was on your dad’s list!?

    106. Ashley says...

      Somewhat related: In an episode of Comedians in Cars Getting Coffee, Seinfeld says that a good way to start a conversation with a stranger is to ask a question that has a number for an answer, i.e. “How long have you lived in this city? How many times have you been here? What time did you wake up today?” Questions with a number for an answer always give you an opportunity for a follow up.

      • Karen says...

        Yup, just added this on my first date sheet for this weekend. Thanks, Ashley.