My Sister’s Awesome Dating Tip

Now that Caroline is dating again, I figured I’d share a little dating tip. When we were in high school, my sister said something that changed the way I approached dating forevermore…

I had a crush on a varsity tennis-player named Ben (shy, dimples, tousled hair, the works) and, after secretly driving by his house (and ducking in the passenger seat) a million times with my girl friends, I decided to take it to the next level and ask him to a movie. That evening, while hanging out at home with my sister, I began analyzing my game plan: when during the day I should call him, how I should phrase the question, which movie I should suggest, whether I should invite other friends along…

My twin sister, who was lying on the sofa, flipping through a magazine, looked up and said, “Here’s the thing with dating: They either like you, or they don’t.”

It sounds random but it was totally liberating. When you’re starting a relationship (or even a friendship), they either like you or they don’t, and the timing of your phone call or the way you say hello/hi/hey/hiya doesn’t matter. Basically, don’t sweat the details.

From then on, for the next decade of dating, I relaxed and felt free to be myself. I’d make corny jokes, I’d call a guy twice in a day if I felt like it, I’d wait to sleep with someone for ages until I was 100% comfortable…and as my sister said, if they liked me, they’d like me (and if they didn’t, they wouldn’t). Those little things wouldn’t change that. It freed me (at least for the most part) from all that overanalyzing and second guessing.

What do you think? What good dating advice have you heard? And what’s your relationship status these days? Is anyone dating right now?

P.S. Four dating tips, and did you have sex on your wedding night?

(Photo from Hotel Chevalier)

  1. Nicole says...


  2. Christine says...

    I’ts the best dating advice ever!!! Thank you very much for it, it helps me a lot. Can’t wait to read the new dating column. You go Girls!

  3. Savannah says...

    All these dating posts are my so true about finding friends! I hope to never be dating again but making new girlfriends is almost scarier to me (their opinions on lots of things definitely matter more than my husbands). This advice is so freeing! I can be as excited as I want to see them and if they like me they like me.

  4. I needed to read this today! I way over analyze everything in dating.. and need to just let it happen!

    One thing I read years ago the helped me was that if you are holding room in your heart for someone you’re waiting for (I once waited for someone for over two years), it may look like you’re single but you give off the vibe that your heart is taken.

    If I could do it over again, I’d mentally let him go, and free up my heart for whomever I met next, and trust that if it’s meant to be, it’ll happen.

    I say this as a currently single woman who needed to read about how if someone likes you, they like you – or they don’t.

  5. All our lives, school has taught us to think deeply, to over-analyze and to prepare a game plan for failing to prepare is preparing to fail. In this subject, love is the main menu and many people fall for the trap. We tend to overthink and entertain paranoia whether “he likes you or not”. All day long, we struggle by fear when in fact, love is characterized by fluidity and spontaneity.

    For someone who has been in and out love like most of us have been to, it’s better to stay organic and let the magic take its toll. When we say magic, it means a MAGIC that no amount of rocket science can fathom or equate. Better to do things that define you as a person or as a woman rather than fit in to a world created by the same set of people who are subtly confused.

    Great post!

    love lots,

  6. I had 2 friends in college that would always hang out in the common area of the dorm mooning over these 2 aloof “too cool for school” guys. The guys knew that the girls were interested and couldn’t have cared less but still my friends sat there sighing night after night.

    One night I said to them, “I don’t bother having crushes on people that don’t have crushes on me.”

    Apparently one of my friends took it to heart and stopped the insanity right away, and from that day forward if I ever got wrapped up in some turkey, she would remind me of my sage advice and help me pull my head out of my butt. It’s been a golden nugget, I tell you.

  7. I really like what you said here about how they either like you or they don’t when it comes to dating or trying to court someone. My wife turned me down a lot when we were younger; however, one day gave in and began to like me. I don’t think a lot of people realize that you can start to like people as well. Thanks for the article!

  8. Betty says...

    I think your sister gave you probably the most important but also the simplest advice about dating and relationships. You don’t need to force a date to happen or a relationship which is not meant to be. This, however, doesn’t mean you don’t have to make an effort . It actually says that you don’t have to worry too much about everything. I was very unsure about flirting and going out with boys until I recently found a website called where people can share their problems and ask for advice. I am now more confident when I go on dates, I know that I have to be myself and to be honest and if the other person is attracted to me, then I guess we are both lucky to have found each other!

  9. I read this post just days before going on a blind date I was really nervous about. For some reason, this really struck a chord with me so I decided to take your advice and to just be myself and if he liked me, he liked me, and if not, it was just one date. It worked! We’re getting married Sept. 4. Thanks for the wonderful advice!

  10. That’s exactly how I’ve always felt about dating. And I’ve never stressed out about getting someone to like me or figuring out of if they do or not.

    I need to share this post with MY sister though. haha.

  11. I like someone seeing their amazing smile and observing how they treat other people. I meet my current boyfriend at a parade that I danced in. I saw him with his friends from afar smiling and being a wall-flower, kind to all. I gave him the come hither finger and I swear we never stopped enjoying ourselves from that point on. I am now pregnant with his baby and I enjoy him more and more every day we spend together.

  12. When is Caroline changing her hair?! I’m really invested in this decision :)

  13. That’s great advice for all relationships in life – clients, coworkers, potential employers at job interviews. Women so often feel the need to over-analyze and be people-pleasers. We should all just lighten up and not take things too personally!

  14. Such good advice! My friend and I danced around each other for a few years, and the relationship was so built up in my head that by the time we finally started dating, I tried to force it (well, to be fair I think we both did). Supposedly, he had everything I needed, but when it came down to it, the relationship took a lot of work and he realized he just really wasn’t interested. Good thing too. My husband makes me the happiest girl in the world, and it’s not hard :)

  15. As corny as it sounds, I had that same epiphany moment after watching “He’s Just Not That Into You.” I always overanalyze and that movie made me let go (… a little).

  16. My (decade-younger) cousin just told me her approach to dating was totally changed by this article, which says that if it’s not a “F* Yeah!”–from both people–it’s a no. (Pardon the language!)

    • Read this article a few months ago and it helped immensely. Ironically, it was shared by the guy I was trying to date. It made me realize that neither of us were a fuck yes, so I proudly decided fuck no. Now I’m dating someone who is head over heels for me and it feels good… but more importantly, it feels easy. :)

  17. I read a great quote once that summed up dating for me: “If he likes you, you will know. If he doesn’t, you will be ‘confused’.”

    Wish I had read it a few months earlier when I went through a long period of confusion! I ended up with a long-time friend who I am not embarrassed around and isn’t embarrassed by me even when I car dance to Copacobana on the radio.

    • Exactly! Glad you ended up with the right person. :)

    • Claudia says...

      Oh my goodness, that is the best quote ever. I have been feeling confused over a guy I met online, we talked every day for the past three weeks, and were on a first date at the end of week two, which went so well. The next day he called me to check on me, being sweet, but then the following week was so hard to get together for a serious of reasons that seemed reasonable. Then it started to just feel strange and on and off in my head about “he’s into me” and “nop, he’s losing interest”. I decided that he was not that into me… stopped texting him to see what he would do and it’s been two days and haven’t heard from him. There you go – Confused! Well, not anymore!

  18. Lucy is so bright

  19. Did we ever get the reveal on Caroline’s haircut choice? If we did, I missed it and I REALLY want to know!

  20. My mom always said “you can’t and don’t have to be perfect for everyone.” I always took things so personally when a relationship ended. It helped immensely.

  21. My dad always used to say that you can tell a lot about a man by the way he treats his mother – I think that is definitely true!

  22. It’s just like in Miranda’s epiphany in SATC, isn’t it? Either he’s into you or he isn’t? I’ve recently moved to a new city and am just starting to think about gong back on the dating scene, so thanks a lot for the reminder!

  23. It took me over a decade of dating people to figure this out. I wish I had someone with that much simple insight in my life back then. Ha!

  24. I love that you posted a story like this! It’s so true. I think almost everyone has had a Ben in their life. I had one too, the problem was that I was also painfully shy and couldn’t muster up the courage to tell him how I felt, until one day when I did. It was so liberating to let him in on my feelings, to let my feelings go. Even though he didn’t feel the same way about me, it still felt awesome. I moved on and never regretted being forward. And I usually look back on that moment when I start to doubt that I can’t do something challenging.

  25. This is great Joanna. I always ask myself when I’m dating someone new, “would I want my son to imitate this person. Would he be a good influence on my son (or daughter)”. If there is hesitation, then there is probably no point in going forward. I always ask this question because I’m a single mother with a son.

  26. Yes! I had a similar revelation when I met my current partner because he was so direct. He liked me, i liked him, we were dating (and still are 6 years later).

    As a single gal, when I realised, “if it’s not a yes, it’s a no”, the pressure was off. No more mixed messages, no more interpreting phone calls, texts, emails. If it’s a “maybe”, “i’m not sure”, “in a little bit”, “i love you, but i’m not in love with you” or whatever other variation, it’s no. Ain’t nobody got time for that!

  27. I’ve been single for a long time. I was hooking up with a friend for about a year. We used to date years ago and stayed friends and started hooking up, then stopped, and started again, and just stopped again. I THINK it’s a blessing in disguise. i have to get out and date but I have no idea where to start. My friend says eye contact. Let’s hope it works!

  28. when i was in 8th grade, my stepmother told me: don’t ever go in the backseat of a car with a boy, he wants to make love to you and that sh*t never works out.

    and then in college, my father told me: don’t be like a doorknob, you don’t guys to have a turn at you.

    thanks family.

  29. Love that! Simple ideas can be so freeing. I love your Mom’s advice too: “You’re only responsible for half the conversation.” How wise and true!

  30. Great advice, thank you!!

  31. Great advice from your sister! I’m happily married, but this advice is definitely something I try to apply to the new friendships I’m making.

    That, and whenever the over-analytical self doubt creeps in over something they said, did, or a look on their face, I repeat the phrase “You’re awesome and people like you.” It actually helps.

  32. Some of the best advice I’ve read is “If a guy is into you, wild horses can’t keep him away” and along with that “You’re the rule, not the exception” as in, if he’s not texting/calling you, it’s not because he dropped his phone in the Grand Canyon, it’s because he’s not into you. Move on.

    Next: Actions speak louder than words. Words are cheap. See if he follows through.

    But I think the key, as others have said, is that YOU need to determine if you’re into HIM, instead of putting the power in his hands.

  33. This is great advice. It seems like there are a lot of unhelpful cliches and articles and books when it comes to dating, but it’s a lot simpler than that, isn’t it? Your sister is so wise.

  34. Thanks for the advice Joanna! I often find myself worrying over what is going on at the other side. This post could not have come at a better time. It is true though, if he is into you it’ll happen but if he isn’t then he isn’t. Simple rules of life to follow by :)

  35. My dating life…well since I’m currently single and even the guys who seem like “good guys” end up leaving me waiting in a parking lot for over an hour never to show up (yep, that just happened yesterday), I don’t have the healthiest outlook on the dating scene. As for how long you should wait? I’d say as long as you can. A former bf of mine told me he knew he liked me because I DIDNT want to put out right away. He said it showed I was serious about a relationship :)

  36. what a gorgeous thing to say. And I totally agree, I used to like people who were sooo not into me when I was a teenager and I’d try so hard to get them to like me. At least I can look back and laugh now :) What an invaluable nugget of wisdom your sister gave you!

    My Froley

  37. This post came at the perfect time. I have had a crush on my perfect man for a very very long time and now I just really want to ask him out even though I am a huge chicken and might pass out in the middle of doing it. I’m totally fine if he says no, but I see him fairly often at my work. I just need to keep remembering that not everyone will have feelings for the people who like them and it is ok. He’s still a good person if he’s not into me.

  38. Super good dating advice! My mom keeps telling me something similar.

  39. Thanks for being spot-on, as always!

    This reminds me of another article/blog I read recently, along the same lines. It’s great advice. It starts with, “Think about this for a moment: Why would you ever choose to be with someone who is not excited to be with you?

    There’s a grey area in dating many people get hung up on — a grey area where feelings are ambiguous or one person has stronger feelings than the other. This grey area causes real, tangible issues. As a man, a huge question is often whether to be persistent and continue pursuing a woman even when she seems lukewarm or hot/cold on your advances. For women, a common question is what to do with men who make their feelings ambiguous.”

  40. Omg! You have a twin sister? So do I! That’s so neat. I’m still pretty young to be giving dating advice, but I’ve had my fair share of broken hearts. I think the best advice I’ve heard that actually applied to me is “Stop looking and it will appear.” It’s so easy to say but so hard to do. After I was hung up over a guy for the good part of a year, I finally began to be happy and focus on myself again. And what do you know? I found my current boyfriend not 4-5 months after and it was completely unexpected and out of the blue!


  41. haha, I’m with your twin sister. Despite believing that, there are times when I have still overanalyzed. And who knows, maybe all the drama/misstep or whatever was in my head and went unnoticed or was unimportant to him. This discussion reminds me of early reality shows of a few years ago that had all this dating advice, or dating gurus — there was one show based in San Francisco, can’t remember the title. But I was hooked for a few episodes while two dating experts would advise women on how to proceed with some dating prospects. It was weird and too much; you followed along on dates, saw the woman preparing, talking on the phone before and after, and so on. It was always orchestrated to look casual and effortless, but it seemed exhausting. Such programs, also ones like The Bachelor, wouldn’t exist if everyone followed your sister’s advice.

  42. I love this!! So simple, yet so true!! I use a similar method. If the guy is not showing interest in the beginning I am moving on. If he already isnt giving me what I want, the he is not the one for me :)

  43. It seems so simple but it’s the best advice. What you say in a text won’t change how someone feels about you. Your sister sounds very smart!

  44. I was a hot mess during my dating years! So that advice would have been awesome. I like how you also correlates it to friendships because I’m slowly getting that! I know we’ve all discussed how difficult it is to make friends in our thirties and I tend to quickly expect people to like/treat me like a close friend, but they may not feel it! So the advice is duly-noted!!

  45. Single and holding steady for almost five years. I’ve gotten into such a routine, especially this last year, living on my own, that I’m okay with being this way for the long haul. I really like my life and I think that’s the key. I don’t need a significant other to feel fulfilled. I have so many other things to fulfill me. It is lonely, though.

  46. That’s a genius tip! Thank goodness for sisters :)

  47. That’s great advice. I’m long married but I am currently trying to make new girlfriends, which feels an awful lot like dating. I’m definitely finding myself sweating the small stuff when it comes to chatting up moms at school or on the playground. It can be pretty rough and scary, I like the idea of shrugging it all off and just being my weird ol self.

  48. This is great advice for sure but more than the advice I like you sister’s attitude. A teenage kid, a girl, that laid back and cool, especially speaking of a subject we the females tend to overthink and drive ourselves crazy about, is very rare and probably one of a kind.

    PS: I really like your posts and your writing style, so easy and pleasant to read.

  49. I’d say that you just need to be honest. Don’t be cryptic! Where did I learn this from? From watching too much K-drama :P -Audrey | Brunch at Audrey’s

  50. I had a similar revelation after watching that Sex in the City episode where Miranda learns that it’s as simple as “he’s not that into you”. Men aren’t that complicated and dating isn’t the subtle art women often think it is.

  51. this is similar to my: “you never have to guess whether a guy likes you…” it’s just obvious. and if you find yourself constantly guessing, there’s your answer. :) #happydating

  52. Easy-peasy advice! Just the way life should be… :)

  53. I was single for a pretty long time and followed these couple ideas: 1) Let his actions tell me who he is (are his actions kind? when he talks about family, does it sound like he genuinely likes family?); 2) Keep in mind that for the first 3 months I’m going to be seeing what I want him to be, so be patient and try to see beyond my own delusion. Both of these things helped me discover who was available – emotionally and spiritually – because I was ok with being single and could enjoy dating until I found someone available to me in that way. There’s a very happy ending to this :)))

  54. Oh my! It is so true. That book “He’s Just Not That Into You” comes to mind. It seems so silly and obvious, but it’s spot on.

  55. I love this advice- I am newly single (after 7 years) and totally agree. It either is or it isn’t. And it’s all good. :)

  56. Not quite a dating comment but similar in it’s simplicity. When I was lamenting to my brother over the fact I had to return to work after my son was born (we had a stay at home mom), he said to me “don’t worry about it, he doesn’t know any different”. It was simple & remarkably soothing.

  57. Great tip! I’ve been terrible at dates, always so nervous… The key is being yourself and think that you have nothing to loose, right? Anne Marie, I thought about Miranda and “He’s not that into you” too.

  58. This is great advice! Sounds like all the women in your family are wise beyond their years. BUT- are we ever going to find out if Caroline got her hair cut? Pictures, please!

  59. this is such great advice, thank you!! I’m starting to date again after a semi recent break up. I’m new to New York City and it has been exciting and awkward and fun. but I really needed this advice. I would love to hear more :)

  60. Thanks for this. I needed it today. I’m dating someone long-distance and find myself reflecting on every little detail when I should be relaxing and enjoying it. He loves me, and he tells me so, and it’s the best feeling in the world. I, too, am looking forward to Caroline’s haircut AND advice from your mom. :) Thanks, Joanna. xo

  61. This is so adorable. And you’re so right. When I finally met my long term boyfriend I texted him ALL the time. And he always texted me right back. All the stupid games of “how long should I wait” or “what should I say” went right out the window because I was always happy to hear from him and he was always happy to hear from me. So novel.

  62. i totally agree about falling in love. and don’t judge a book by its cover. my husband is hotter today than the day i met him and that was 20 years ago!

  63. I believe in being totally up front right away. I met my husband on halloween and was separated from my previous husband and trying to get divorced. We were both at a party and I was leaving to go meet some friends so I said ” look I’m married but trying to get divorced, I have to leave, and you can have my number if you want it”. He said ” I want it”
    Flash forward to first date, I said ” if you do drugs I wont date you. I want kids and if you do not, I wont date you, and I only sleep with one person at a time and Im not saying I will sleep with you.”
    Seems so funny now and I probably sounded like a crazy person but 3 years later we are happily married and expecting a baby this november!
    So put it out there! if they cant handle it enough to stick around, they aren’t the one.

  64. another piece of advice i would give people is that you can FALL in love. it doesn’t have to be love at first site, or instant chemistry. give it a chance. you may be surprised by how deep and wonderful someone is once you get to know them, and who you end up falling in love with.

  65. theresa, we’ll post a photo soon! you’re so sweet :)

  66. Still waiting for the update on Caroline’s hair!! What haircut did she end up getting?!

  67. Your sister is very wise! Don’t worry about Ben Joanna – you got your tousled-haired dimpled love in the end!

  68. I’m with Mary Anne. I’ve been single a while and a recently single friend was agonizing over whether or not a guy she was going on a date with would like her. I immediately responded with “Who cares!? You don’t even know if you like HIM!” It’s so easy to get caught up in what other people might think of you, that you can totally lose perspective.

    My other dating advice for the newly single is just to give it a minute. All I learned from the first few dates I went on after a long-term relationship ended was that I was NOT ready to be dating yet. Or at least not seriously. Flirt yes, go on dates, yes, but be carefyl not to just insert someone else into the relationship you just got out of, if that makes sense?

  69. Ha! My husband would appreciate this post. He always says the difference between a guy coming off as a keeper or a creeper is whether or not the girl liked him.

  70. gaaaah! i HATE when women tell me that they’re only attracted to The Bad Boy. as MY grandma would say, “don’t date someone you wouldn’t marry”. so, good luck with the bad boy husband. me? i married a gem!

  71. Your twin is absolutely right! My twin sister is usually the voice of reason for me too.

  72. Amazingly, helpful and simple. When I think about whether I like someone or not and then the timing, words, etc., it’s like, yep, that’s such a true point!

  73. That’s such liberating advice. The book “He’s Just Not That Into You” is based on that premise and totally changed how I thought about dating and relationships in college. It’s totally different than the movie of the same name and I still loan my copy to girlfriends when they’re going through tough patches in relationships or breakups. Even as a happily coupled person the advice can be a great reminder to stay true to oneself.

  74. Thanks so much for this post, Joanna! I am recently back into the dating game for the first time in a few years, and after a few semi-failed attempts, I really needed this! Hopefully I can follow your sister’s smart advice to be myself and just let things be.

  75. In college, I was agonizing about whether or not I liked the boy who asked me out on a date and my dad’s sage advice has stuck with me always: “Life is too short to dance with ugly women” — thanks Dad! : )

  76. When I was about 3 months into dating my now husband, I laid out for him the things that I wanted in the future. I basically said “This is what I want, and if this isn’t what you want, I need to know now, because if it isn’t then I’d rather not invest my time.” My friends always say things like “that was so brave of you!” “I can’t believe you did that!” to which I think, “Meh, either he would want it or he wouldn’t, and if he didn’t then I didn’t want him.”

    I agree either they want to be with you, or they don’t, and Shakiria is right, you can’t force yourself to be interested either. Laying it out on the table, I think, was one of the smartest things I ever did.

  77. aaahhh, I need to know if Caroline got her hair cut!

  78. mary anne, I LOVE THAT! and this is random, but when i would get nervous before dates, my mom would always say, “you’re only responsible for half the conversation.” that always made me feel better.

  79. youandmeandwallie, i love that advice, i think it’s so true. i also love the grandmotherly advice to “date someone nice,” because that really does matter when you’re building a life with someone. you’ll always go through ups and downs and you want someone who is nice to you throughout (and you to them).

  80. Thanks for sharing this, Jo! I hope you’ll add a link to Caroline’s beautiful, recent post on her broken heart ( We’ve all been there and life does, indeed, go one (even if we don’t believe it at the time). Brava, Caroline! Sending lots of love your way! : )

  81. So, so true! Once I started just being my weird self, I had so much more fun (and luck) dating. I didn’t hesitate to move on if I wasn’t into him, or he wasn’t in to me, because I knew we’d both be happier that way anyway.
    Then I wound up dating and marrying a good friend of mine, who had seen my personality for all of its quirks for years, and now even encourages me to embrace and further my quirks.
    Nothing is more exhausting and draining than trying to project a fake persona. THE WORST.

  82. Love this advice. I was always too nervous to initiate anything, so I always waited for a guy to ask me out…then one day, I asked out a guy because I knew if I didnt say something, I may not see him again…and 6 years later, he became my husband. He loves telling people that story :)

  83. I don’t remember where I saw/heard it, but I read once that when going on a date, don’t think “I hope he likes me.” Think: “I hope I like him.” Because that’s what matters. Changing that mindset really changed my attitude walking into a date and gave me the confidence that probably made me more attractive to others anyway.

  84. aww haha mh, well, sadly, he wasn’t into me, and we never went to the movie!

  85. Love it! It also subtly drives home the point that it’s important not to change who YOU are for whoever you’re dating :)

    Thanks for sharing! I have a twin sister too, I and think that twin advice is the best (it’s so unfiltered.)

  86. This is great Joanna! I love your blog.

    I would offer up the reverse as being equally true. You either like them or you don’t.

    I’m one of those big-hearted people who feels horrible for not liking a guy who looks amazing on paper.

    You can’t force it. It’s either there or it isn’t. Anything outside of that is inauthentic.


  87. it’s like that scen in SATC where Miranda is liberated by “He’s just not that into you”.

  88. The beginning should be easy. Advice from my mom. I’ve met far too many couples who started counseling after a few months of dating or are arguing after a few dates. If its not working early on, why keep pursuing it?

  89. This is great advice! Simple yet freeing. I am back in the dating pool after a tough breakup (what breakup ISN’T though, am I right?) so this is sound advice I shall follow. Thanks.

  90. So, did he like you?! I mean, you can’t tell us that story and not tell us the ending! What happened with Ben?