Date Conversation Topics

6 Date Conversation Topics

What do you usually talk about on a date?

I don’t know about you, but I am of the mind that a date should not feel like a job interview. When a well-meaning person asks, “Which famous person, living or dead, would you invite to dinner?” I want to say (as politely as possible), “Someone who wouldn’t ask questions like that.” Instead, here are a few topics I’ve found spark great conversation…

Find commonalities. Don’t let go.
If you have any acquaintances in common, bonus points for you. Otherwise, cover your bases — siblings, hobbies, pets, favorite travel destinations — until you hit common ground. Discussing your mutual love of surfing or Jonathan Franzen novels is the easiest way to bond early on.

What’s the worst/weirdest date you’ve ever been on?
While talking about exes is generally a no-no, this question has yielded some amazing responses. For me, it’s the story of the time I met two people named Rob in a very similar timeframe. One was a Rob I wanted to date. One was a Rob I did not. I made a date with Rob-I-liked, and when I arrived at the bar… it was the wrong Rob. I had no choice but to sit it out, cursing the ambiguity of text messages.

Did you have an irrational childhood fear?
I was afraid of wolves. I swore they hid in the closets, waiting to eat me. A date was afraid of stickers. (Yes, stickers.) These things can be surprisingly fun to talk about. While we’re at it… talking about youth is generally a good time. Did you have a favorite dinosaur? A quirky pet? If you’re similar ages, you can discuss your feelings about Full House or The Wonder Years or the frighteningly robust POG collection languishing in your parents’ basement.

Have you read anything good lately?
I’m always poking around to see what people are reading. Whether it’s a graphic novel, a magazine article or an interview with their favorite comedian, discussing things you’ve read is a great way to see what makes them tick.

What’s your secret talent?
It could be anything from yodeling to deep sea diving, but everyone loves to talk about times when they shine. As for me, I can hula hoop for hours at a time, while performing tricks like a trained seal. I never get to talk about this, but you know what? I’d like to. Asking your date to boast leads to them feeling great in your presence. Everybody wins.

If you had to be trapped inside one giant food, and the only way to escape was to eat your way out of it, which food would you choose?
Yes, this is essentially the same as asking someone what their favorite food is. But it’s a much more fun way to phrase it, and it typically yields a better response. Mine is a toss up between a large hunk of cheddar cheese and a peanut butter cup.

Finally, if you do find yourself in the midst of a quiet moment, remember that silence has its place in conversations, too. You know when Harry tells Sally, “It’s so nice when you can sit with someone and not have to talk”? That is true. The more at ease you are, the more at ease your company will feel.

Do you have any go-to conversation starters? Or any questions you love to be asked?

P.S. An awesome dating tip and are you okay with conversational pauses?

(Photo of Jane Birkin and Serge Gainbourg by Ian Berry, 1970)

  1. Lisa says...

    Good question to ask is, tell me a fond story about your mother. It will clue you in pretty quickly on how he feels about women.
    P.S. I bought a hula hoop. I think it’s broken, can’t get it to spin! LOL

  2. Mary says...

    Not to nitpick, but I don’t think that quote from WHMS is meant to me taken at face value. They are definitely not at ease in that scene — it’s a very awkward post-sex breakfast!

    • Emmanuella says...

      haha, I was thinking the same thing. Now when the same thing is said in Pulp Fiction, I think Mia and (John Travolta’s character whose name I forget and don’t feel like looking up) did mean it… but she o.d’s so maybe she got a little too comfortable and the moral is to keep talking. I also love that line from Best In Show “we can talk or not talk for hours”

  3. Pearl says...

    POGS! yes.

  4. I recently went on a date with a guy who mentioned that he got goosebumps when talking about his favorite team. I’m not a sports person so I followed up with, “What other kinds of things give you goosebumps?” Aside from commonalities, I love getting people to talk about what excites them. Even if the subject is unknown to you, their passion will likely be contagious and they may teach you something in the process. Also, I have been reading your site for a few months now and I love it. Thanks for the posts!

  5. Caitlin says...

    I teach high school, and I have a very quiet group of students this year. Some of them told me recently that many of them don’t know the other students in class and are afraid to talk to each other! We used a bunch of these questions in a get-to-know-you activity today. Thanks! :)

    • Joanna Goddard says...

      that is so cool! thanks for sharing, caitlin! you sound like an awesome teacher.

  6. Haha my favorite, BY FAR, is “If you had to be trapped inside one giant food, and the only way to escape was to eat your way out of it, which food would you choose?” I am definitely adding this one to my repertoire.

  7. Despina says...

    A question I like is “which cartoon/shows did you use to watch as a child”. It scores points especially if the age difference is not huge. It’s all about finding common ground methinks…

  8. music! I met all of my bfs and now husband through gigs / clubs / DJ events… It’s my major passion so you’d have to be able to have a good music convo. :) (Never trust anyone who doesn’t like the Beatles.)

  9. Kelly says...

    Best one ever for a large group of people: If you could have one super power, would you fly or be invisible? (American Life Podcast)

  10. Emily says...

    Caroline, here’s your opportunity: please tell us more about your epic hula hooping skills! Some questions to get you started writing a post I know we’ll *all* enjoy reading:
    – when did you start hooping?
    – were you a natural or did it take a while to learn?
    – do you hoop often?
    – do you hoop with others? (ie are you the type who goes to any and all festivals with your colorful hoop in hand to find your people, or do you privately hoop in your living room? if the latter, do you feel lonely when you hoop? <– this is a sad but also hilarious mental image.)
    – what's your favorite trick?
    – do you have killer abs because of your secret talent?

    I finally got the knack of hula hooping at about 19 years old, and I don't own one, so I rarely have the opportunity to do it. I'm tempted to get one, because they're so fun and because I bet it would tone my belly some, but I'm too embarrassed to just hang out in the yard hula hooping. Maybe if you write this post I'll get over it and hoop freely ;)

    • Trish says...

      Ooooo, do get one .
      It’s the best fun and great exercise . I go to hoop classes (to learn tricks) every week.
      My abs are not killer but I can keep the hoop going for ages ;-)

    • Yes!! Please tell us more, Caroline! I’d read it :)

  11. I was recently on a first date with a guy (yay for dating in your 30s!) who asked, “What is one personality trait you hope other people pick up on about you?” It really caught me off guard, and at first I felt a little funny answering. But it led to my taking a moment to think about what I like about myself. I told him I wanted other people to see me as someone who is present and lives in the moment. He then asked if i was living in the moment right then with him. It was kind of a sexy, intimate exchange. :)

  12. Haven’t been on a date with anyone new for ages – just got engaged! – but I like asking them about their hobbies, favourite food, and music! I agree with finding a common ground. It makes the conversation flow so smoothly. I strangely also like asking them if they know any good jokes. Humour is so important!

    X Min,

  13. “If you had to be trapped inside one giant food…” FLAMING CHEETOS. yes, i’m 13 forever.

    • Bri says...


  14. Hali says...

    These are brilliant! I just asked my boyfriend of 6 years the food question and at first he looked so perplexed, then he answered very seriously, “well, it would have to be hollow or else you couldn’t move.” I busted up laughing! And then he said “a grape would be nice though because you could slide around a bit inside and then if you had to, you could punch a hole through the skin to break out.” He never eats grapes? I love that man.

    • this is so cute.

    • Ha! I just asked my husband this too and he said “watermelon,” which struck me as really odd, considering he never really eats it. His rational was that it would be mostly liquid so it would be easy to eat a lot of it without getting too full. I think he’s just saying this because it’s 95 degrees in San Francisco. I also thought it was hilarious that he followed that, without prompting, “well, I wouldn’t pick something like cheese. That would be just awful.” Men are odd!

  15. Brittany says...

    I always find a way to ask what five words they would choose to describe themselves in high school or college with, depending on how old they are. It’s interesting to see what they say and it’s so much more profound than other get to know you questions can be! Plus it always leads to stories :)

  16. i just laughed out loud at the POG comment!

  17. Hannah says...

    I haven’t been on a date in forever, but my new favorite question to ask people is “Lennon or McCartney?” I saw a British documentary that basically just asks musicians that question, and I thought the responses were fascinating! (I’m McCartney all the way, although when I was younger, I’m sure I would have said Lennon.)

  18. Cait says...

    Thank God for Caroline, it’s nice to know I’m not the only 31 year old woman still in the early dating stages when seemingly everyone has an adorable husband and at least one adorable child :)

    • Lissi says...

      No, there are definitely more of us out there :-)

  19. Susan M. says...

    Good ideas — I go for 1 and 4, although I feel embarrassed about putting people on the spot about their reading. Looking for commonalities is important early on. Discovering if someone has a similar sense of humour. I think one thing really hard to do on a first date, especially when one is not sure where it will go, is to give it time to happen, to really listen to the other person. A true listener can have great conversations, but it’s easier said than done. (and of course there’s the worry about silences or seeming too passive.) I don’t know if I could be as entertaining as Caroline :)

  20. I ask them who they are voting for. I’m totally down for talking about views on politics, religion, and all those other taboo subjects right away. I don’t have a ton of time so I’m not going to waste my time going on multiple dates with someone who is going to vote for Trump. (Aka my last date)

    • Tracey says...

      Ha! At least you probably got some good stories
      from that date!

  21. Talking about about TV shows or good movies worked so far really good, because there are many good shows and it’s always good to know someone who likes the same things as I do.

    • Joanna Goddard says...

      So true! Everyone has a strong opinion on movies and TV. :)

  22. Nina says...

    These are good. I really enjoy Would You Rather questions when you’re stuck for something to talk about. I really despise dates who talk talk talk about themselves and never ask you or listen. I really liked when someone said” tell me about that” when I said something that surprised them. I also like to use” tell me more about that. ” seems like in our fast digital age we encourage sound bite conversations and I want more! I’d like a video of the hulahooping! I think we were all raised with it being trained seals whether they were seals or sea lions ;)

  23. Kate says...

    I went on a first date yesterday, and we ended up talking at length about the fact that we both suffer from motion sickness. From Dramamine and Sea Bands to times where we were sitting on the side of the road or fighting to stay in the front seat of a car, it was certainly not a romantic or sexy conversation but it was the thing I remember the most and certainly a bonding moment!

  24. It’s been forever since I’ve been on a first date, but I start conversations with strangers all the time… and the ‘secret power’ one is so good. This past weekend at a BBQ, someone was having a hard time opening a beer and I just said “Oh, I’ll open that! My super-power is that I can open any bottle. Beer, wine, champagne, seltzer…” Then everyone said stuff like “With your bare hands? With your teeth?” I was like, “No! With a bottle opener when necessary. Ok, maybe ‘superpower’ was a little bit of an overstatement…”

  25. Liz says...

    <3 Serge always. He's so sexy And Jane is so lovely.

    • Yes! I love them. Do you have the coffee table book of photos of them?

  26. I love these topics, especially the last one. I find most get-to-know topics really don’t help you know a person at all, but these definitely would.

    Kristi | Be Loverly

  27. These topics are aaaamazing! I’ve been dating my boyfriend for over a year but I still want to find out what food he’d choose to eat his way out of!


  28. Bekah says...

    i recently read that one of the best things to do is be self-revelatory. i think most people reading this are aware of what a turn-off narcissism is and how important it is to listen – not negating that AT ALL – but i think one of the best ways to get the guy i’m dating to talk is to tell him something about myself and let him respond so we can get in a flow. i love podcasts, for instance, so telling him about some of my favorites and then having him pull out his phone to talk about some of his turned out to be a great way to get to know him better.

  29. Katie says...

    Great post, Caroline! These would work for any new people you meet, not just in date settings. Storing these away for future use…

    I am going to nerd out, please bear with me, but I think you mean sea lion, not seal :) Sea lions have all the talent!

    • Heather says...

      LOL! I’m always correcting people on the difference between seals and sea lions!

  30. Dee says...

    For dates, or husbands, I really like top trumps style questions, but really really specific e.g. hazelnut or macadamia? Lobster or crab? Or else favourite questions of really specific categories e.g. Favourite shellfish? Favourite brand of gin?

  31. Kelly says...

    This is obviously a photo of Taylor Swift and Bruce Springsteen, right?!?

    Haha! The resemblance is uncanny!

    • Annabel says...

      OH my god, yes! Haha, so true :)

  32. Simone says...

    I would totally eat my way out of banana pudding – the REAL kind, not a box of instant pudding with sliced bananas and Nilla wafers. That is not the real banana pudding!

  33. ashley b says...

    loving your posts as always caroline.

    these are great tips. i’d add one: LISTEN (and let the conversation find itself). i find sadly that so many of my dates are just rambling off questions and not even listening to how i answer. or worse yet they’re just going on about themselves. listening can lead to surprising turns in the conversation rather than another date consisting of Q&A.

  34. A lot of dating advice is cliche or useless. These are really good tips (even though I’ve been dating my husband for 13 years now). Oh, and I’d like to eat my way out of a key lime pie.

  35. Lauren E. says...

    On our first date, I said to my (now)boyfriend, “So, tell me something I don’t know about you.” And he immediately responded, “I hate that question.” At the time I thought that was so rude, but it taught me a) he was not a conventional guy, and b) he was brutally honest. It also let me know I could be my sarcastic, snarky self with him and five years later we still laugh about it.

    I’d eat my way out of a giant pancake :)

  36. I love all of these! I TOTALLY agree that asking someone what they would eat their way out of is way more fun than asking them what their favorite food is. Because then you can imagine being inside an enormous ball of chocolate chip cookie dough (in my case).

    It’s funny — on our first phone call, my now-boyfriend (of 2.5 years) was actually super intense, and asked me “What’s important to you in life?” It kind of freaked me out at the time, but it ended up leading to a really great and authentic conversation, and set the tone for the rest of our relationship. I had always been someone who wanted to keep things light and fun and (frankly) inoffensive on a first date, but he taught me that sometimes it’s okay to just totally show up as yourself. After we got to know each other, he told me that he had purposefully been as much himself as possible, because he’d get rid of the people who didn’t want to date him asap. Anyway, I thought it was a kind of amazing thing.

  37. The “secret talent” one is awfully similar to that stressful OkCupid question “I’m really good at…” though. My online dating clients struggle with that one all the time! :)

    My suggestion if someone poses these kinds of thoughtful questions to YOU and they make you nervous is to go with self deprecation. If you can poke fun at yourself (my example is that I’m really good at *thinking* I’ve perfectly poured a fizzy beverage, only to have it foam up and overflow at the last possible instant) it showcases a kind of humor and gets you laughing and loosening up.

    After all, the point doesn’t have to be to brag—so if you’re not as comfortable with hula-boasting as Caroline is (another thing I suck at by the way, haha, but I’ve gotten good at twirling them on my arms) then don’t feel like you’re failing at date-talk. When you can poke fun at yourself with grace, it actually comes off as the same level of confident as Caroline’s more straightforward confidence—you are sort of conveying that you feel good enough about yourself that admitting your minor failures or awkward moments is charming, not a turnoff.

  38. Letra says...

    I was on a date a few weeks ago at a Japanese restaurant and my date asked, “If you had to name your firstborn child after a sushi roll on this menu, what would it be?”

    His was Spicy Tuna.

    If all else fails, weird questions relating to the menu make for great conversation.

  39. karina says...

    Great article and really useful tips! I love your writing, Caroline.

  40. I’m going to ask my husband the eat your way out of something right now, though I suspect his answer (like mine) would be pizza! Fun post :)

  41. Cindy says...

    My number one go-to conversation starter (all situations) is, “What did your week look like?” How many times have I been indebted to this one question for being the basis of an entire encounter with another person? I find out all kinds of stuff. I find out what potential points of commonality for conversation later on, but I also find out what kind of person he/she is (for example, if he is a complainer, I’ll know right away). It’s a super non-threatening question, too: everyone can talk you through the week. I also like that it avoids the ubiquitous and awful, “So what do you do?”

    Great post, Caroline: I love seeing your name pop up!

    • Angela says...

      love that question! I am definitely going to start using it regularly.

  42. Heather says...

    Also – What is this photo? Serge Gainsbourg and Jane Birkin?

    • Joanna Goddard says...

      yes, you got it!

  43. Heather says...

    “the frighteningly robust POG collection languishing in your parents’ basement.” HAAH!!! yes. dead on.

  44. In the age of internet dating, I have definitely been on dates that seemed more like job interviews than dates. They were the WORST! I think successful dates are ones where you are already talking like a couple that cares about one another, asking questions like how was your day? How’d work go? Things like that. I know that’s what hit it off with me and my now husband. No pressure, just fun.

    Analog House

  45. Love these! I’ve had success with the “worst date story,” “irrational childhood fear,” (I knew a guy who had a phobia of BUTTONS) and “secret talent” questions.

    I also pose the favorite food question by asking my date what their last meal on death row would be. Slightly dark and morbid, but oh well. It also provides a good platform to discuss the Buzzfeed article I read once which showed that most people seem to order steak and one person once ordered pints and pints of mint chocolate chip ice-cream…

    I’ve also asked the question, “what is one of the peak experiences that you’ve experience in your life so far?” (Answers: the red, red mountains against the Arizona sky, tuna fishing at 4 am on a boat in the middle of the Atlantic ocean, a four meal with extended family on a terrace in Tuscany with a cotton-candy sunset…) That question yields some breathtaking, incredible stories that leaves both people feeling expanded, regardless of whether there was a “connection” or not.

    • Joanna Goddard says...

      good tips!! a babysitter we once hired had a phobia of MILK. she asked if it was okay for her not to wash out anton’s bottle and instead just leave it in the sink.

    • I love the peak experiences question. Sometimes it’s something grand and sometimes it’s a simple moment like sitting on a bench on Martha’s Vineyard at sunset while my kids happily gobbled a huge bag of candy.

  46. Megan Lakely says...

    LOLed at the last one. I ask about siblings since you can learn so much about someone’s family and background. There are usually funny stories involved too.

  47. These are great! I’m not dating anymore, but I will definitely be using these at our dinner party on Saturday.

  48. I love these questions! #4 is probably my favorite question to ask. I like getting to know people and hearing a bit of the stories, so intentional questions are great in my book. But you’re right, it’s easy for get to know you questions to tread too closely to job interview questions, and no one likes those. Just thinking about trying to articulate what my greatest strengths and weaknesses are makes me sweat.

    Lynn-Holly | The Fisher Files

  49. Mary Jenkins says...

    I would eat my way out of either fresh mozzarella or any sort of fruit crumble. Love you, Caroline!

    • Joanna Goddard says...

      i would do a flourless chocolate cake or cacio e pepe.

  50. Mollie says...

    These are great! We’re far beyond our first date, but I still don’t know what my husband would say to some of these questions. Definitely going to ask!

    • Joanna Goddard says...

      agreed! it can be really fun to ask offbeat questions and learn something new about a long-time partner. that’s why i love random passing-the-time games like Would You Rather — it can be really surprising!

  51. as an american expat living in berlin i often come across people who had a very different upbringing than i did. i love asking dates about their lives growing up. it’s a great way to get someone talking about themselves while also learning about some interesting cultural nuances!

  52. Charlotte says...

    Thank you Caroline! Nr 2 and 6 Whaaaahahahahaaa
    Btw I would be trapped in a Napolitana pizza

  53. “If you were a dessert, what would you be?”

    also, if they went to school, “What colleges did you apply to?” It lets them talk about where they thought they were going in life, or an experience they haven’t gotten to talk about since they were 17!

  54. sarah says...

    really enjoyed these! talking about the time someone has been most nervous (ever in their life) also leads to interesting and often poignant conversations. i don’t usually comment but wanted to let you know that i enjoyed your writing style in this, caroline. i think either you or joanna said something about you working on a book? i hope that’s true!! i’d be super curious to read it.