#227: Three dates, no kiss

Kiss me Kiss me Kiss Me by The CureDear Captain Awkward,

I am going to try and make a long story short. For months (and months), I ogled a handsome coworker from afar (actually not from afar; from pretty close). Never in a million years did I think this guy would entertain the idea of going out with me (I was your typical newspaper staff nerd/underacheiver in high school; he was a 4.0 football player, I’m talkative, he’s extremely quiet, etc.) – but, after months of debating whether or not to ask him out, I finally did and he said yes. Fast-forward a bit. We’ve hung out about three or four times now and we get along well, have plenty to talk about, and make each other laugh. He wants to pay for my food when we go out to eat (I let him the first time, but I covered my half to his dismay the second – just because I don’t want him to associate me with draining his wallet). Everything seems to say “date” when we go out and yet … there’s a catch.

Enter the awkward.

The past two times we hung out (I’m not even going to count the first time during which we simply parted with a smile and a wave), we’ve parted ways with a hug. A HUG. We are in our twenties, Captain, and I’m not saying I want to rush things, but why hasn’t this guy tried to kiss me? Sometimes I conclude that I’ve been shoved (never to emerge again) headfirst into the Friend Zone. I don’t want to push him (or make things more awkward by bringing it up) away. What do you think?

Hi there!

What do I think?

I think you should let go of defining yourself (and this dude) as being the “typical” anything according to who you were in high school.

I think that you should let go of the idea that it’s the man’s job to initiate the kissing stuff the way you’ve let go of the idea that it’s his job to do the paying for stuff. Do you want to kiss him? Then the next time you go out, ask if you can kiss him and see how that goes.

I think that the thing where you don’t want to “make it more awkward” is why this blog exists. It’s already awkward. You want to kiss him, and you’re not sure he wants to kiss you. By moving things along, you’re just making it differently awkward, and one step closer to maybe getting what you want.

Reporting Live from the Metanarrative: If you’re a straight woman, I get that it feels totally awesome and right to have a handsome man you like move in for that first kiss or ask if he can kiss you.  It’s what you’ve been trained to want by every representation of romance in the media ever (exception below), and then it feels really good on its own because hey, kissing!, and it makes you feel pretty and chosen? So it rings all the bells of “This is what romance is like!” You’re not ruining feminism if you like that (I really, really like that).

But I think that it feels really good for humans to be desired by other humans that they desire, full stop. “A human I like wants to kiss me!”  Gay people have to navigate that all the time without worrying about whose “job” it is to do the kissing, so take a lesson from them and go for it.

If he’s not into your kisses, he’ll tell you, and then you’ll know. It will be differently awkward, but totally survivable and ok.

33 thoughts on “#227: Three dates, no kiss

  1. Actually, when my now husband and I first went out, he asked if he could kiss me, and it felt TOTALLY WEIRD for him to ask me. Why didn’t he just do it? I guess I’d never had anyone verbalize what they wanted before. Sign #1 that he was better for me than the others, I suppose!

    Good luck, LW. Just try it, and it’ll be resolved either way. I will hope on your behalf that he responds the way you want him to!

  2. Kiss away! You asked him out, right? Maybe he doesn’t like making the first move. Maybe he’s scared of making things awkward.

    HOWEVER CAVEAT WARNING: there is a slight possibility that he took your paying for part of the meal/activity as a non-interest flag. Which, if true, also leads to a slight possibility that he has some retrograde ideas about women/men/dating/money/etc. (Well, let’s be honest. The possibility that he has some retrograde ideas about those things is sky high, because, the patriarchy/capitalism. But hopefully he is well on his journey to Feminist/Humanist good times.) So just be aware. Maybe take him bowling, to see if he’ll use the pink bowling ball.

    1. This is what I was going to say. Some well-meaning idiot may have told him that going dutch means it’s not a date. Disabuse him of this notion! Also, I had this same problem with a dude I dated a while back and it turned out he just wasn’t picking up what I was putting down. I had to use my words, and then yay! Makeouts!

    2. I agree with the caveat. As a someone who floats the feminist/traditional dating line, I had to be told at one point that lots of men like to pay for dates because it feels sexy to be generous — think of it as a version of a pretty bra?

      Dating in the current age? Complicated. Which is why using anything we’d like from our tool chest — dating paying, pretty lingerie, WORDS, kissing, is all worth using in combination. So, yes, totally kiss the guy.

      You can also try out the less agressive sexy moves first, like putting a hand on the arm/hand/small of the back and see how that works out. Has there been any of that? When I like someone, I usually really, really want to touch them.

      Also helpful to kissing bravery? Setting the scene. I like sexy walks to pretty, secluded, romantic places, like parks with groves of trees, pretty bandshells, or the Tadao Ando room at the Art Institute.

    3. “Maybe he doesn’t like making the first move. Maybe he’s scared of making things awkward.”

      This! Maybe he’s wondering why you haven’t kissed him. Maybe he hasn’t kissed many people. Maybe he’s worried about offending you or making you think he’s only interested in a physical relationship. Maybe he’s missed all your signals about how much you’d like to kiss him. Maybe he’s picky about who he kisses and hasn’t decided if he wants to go there with you. Maybe he thinks he has bad breath. Maybe someone’s told him he’s a bad kisser. There are many possibilities.

      LW, kiss him! Or don’t kiss him. Or, the next time you part, smile slightly mischeviously and say, “How about a goodnight kiss?” Whatever’s more your style.

      1. Also, maybe I am weird and and socially malfunctioning, but three dates doesn’t seem like a ridiculously long time to go without a kiss? You are still getting to know each other! I mean, yes, you work together, but now you are getting to know each other in a different context. Personally, I would barely be holdong someone’s hand after three dates, because that is my speed and that is okay.

  3. In my late teens or early twenties, there was this beautiful, intelligent, mysterious man I desired. He went on a couple of dates(?) with me and was generally all flirtatious, and I was wondering what on earth was going on and should I kiss him or not? Finally, I decided to go for it, and he actually dodged out of the way. It was humiliating, and I sobbed my heart out into my roommate’s shoulder afterward, but when I finally got to where I could be like, “Hey, so I tried to kiss you and you DODGED. I am guessing you’re not into me like I thought you were,” he admitted that he was only dating me to try and get over his ex girlfriend, and actually he wasn’t over her at all, and he didn’t realize this until I tried to kiss him on date two.

    But you know what? If I hadn’t just freaking GONE for it, I would have gone on who knows how many more Oh My God Is This A Date Or Not For Reals. And I dated many more people after that, and anyway, dating is like interviewing for a job. If you don’t get the job, whatever. You got some practice, and you learned some techniques for next time, and maybe it wasn’t that you’re awful, but they already picked someone and were interviewing others as a sort of competitive bidding process anyway.

    1. Which is not to assume that he is just not into you, but to say, the worst that can happen is what happened to me, and actually that wasn’t so bad when it came down to it, so you have nothing to lose and go for it!

  4. One thing that wasn’t in the letter: is letter writer picking up “sex vibes” from this guy (or I guess romance vibes, or whatever non-spinster people feel)? That would be the deciding factor if I were in that situation. (Obviously LW is not me and different strokes, blah blah).

      1. I don’t mean “trying.” I mean, do you think the guy wants to kiss/fuck/whatever? When I think of my own experiences my gut is usually right. If I think they want it, I offer. If I don’t get that vibe, we hang out as non-physical friends, if that’s what I want with them, or if not we stop hanging out.

        1. No, you’re totally correct! It’s hard to define what Commander Logic calls “groin.”


    I think you should let go of defining yourself (and this dude) as being the “typical” anything according to who you were in high school.

    I think that you should let go of the idea that it’s the man’s job to initiate the kissing stuff the way you’ve let go of the idea that it’s his job to do the paying for stuff. Do you want to kiss him? Then the next time you go out, ask if you can kiss him and see how that goes.


    If you’re a straight woman, I get that it feels totally awesome and right to have a handsome man you like move in for that first kiss or ask if he can kiss you. It’s what you’ve been trained to want by every representation of romance in the media ever (exception below), and then it feels really good on its own because hey, kissing!, and it makes you feel pretty and chosen? So it rings all the bells of “This is what romance is like!”.

    Case in point, dear LW: as far as “conventional and socially acceptable dating patterns” go, my current boyfriend and I did everything backwards: we slept together first and then we started dating–with me asking him out–and you know what? I’ve never been with someone who was so eager to please me, both inside and outside of the sack; I’ve never had more engaging, funny and sometimes downright bizarre conversation with him; and basically I have never been more smitten with someone in my entire LIFE. Did I also mention we’re both coworkers too?

    Your relationship will this dude is not FOREVER DOOMED just because you haven’t or he hasn’t kissed you yet or whatever else society has made you feel is some sort of Relationship Milestone You Need To Reach By A Certain Point Or Else You Blew It With Him Oh My God How Could You! The sooner you let go the idea that YOUR–not everyone else’s/society’s, but YOUR–method of romancing this fellow may not follow conventional standards, the more likely you’re actually going to get this guy, because guess what? What works for everyone else, will not necessarily work for you! And I understand that actually adopting this mindset and working your relationships around it is way easier said than done: before I asked him out there were time I felt all depressed and anxious about AM I DOING THIS RIGHT?? SHOULD I BACK OFF OH GOD WHAT AM I EVEN and then I would go from being all confident and knowing what I want to making sure I’d wait for him to call me and I’d get irrationally disappointed when he didn’t, never mind the fact he’s not a freaking mind reader. That, and it sends mixed signals like woah, which, if you’re serious about getting this dude, is Never A Good Thing.

    If you want to wait for this guy to make the moves on you? Great! If you want to make the moves on him? Awesome! Do whatever works and feels best for you two, and know that there is no stigma whatsoever for making the first move, if that is what you want to do. Most of all, don’t be afraid to do it! Best of luck to you!

    /silently taps off Caps Lock button

  6. You say “he’s extremely quiet”. Maybe he’s a bit shy, too.

    I’m actually in a similar situation right now. Tomorrow will be the third date with a wonderful woman, but we are taking things slow. I am somewhat shy and inexperienced (especially for my age), so I don’t want to go too fast and mess things up. On our second date we cuddled on a park bench and watched the sunset for awhile, then held hands on the way back to the car.

    While sitting together I used my words and we talked about things. I don’t think it was awkward, even though I admitted how scared I was. It’s good to open up and be vulnerable sometimes.

    So I say talk to him about it. Use your words. Good luck.

  7. I have felt your pain, frustration and confusion. You are not alone.

    When you asked him out for the first time did you actually use the word ‘date’?
    As in “I want to go out on a date?”

    If not, then maybe he is unclear what you wanted originally and explain his hesitancy. He doesn’t really know the reason why you were asking him out.

    As I am a gay man I learned some years ago that when I ask a guy out I make it clear that what I am looking for is a ‘date’. Other often similar terms can make for confusing signals.
    By making my intentions clear and direct then there is no room for confusion.

    I agree with everyone else that at this point you should just kiss him. It may end up awkward. Or he maybe greatly relieved. And you too!

  8. The chance of this is remote, but maybe he’s asexual? In which case the idea of kissing you may not having occurred to him. Knowing that:

    a) Many Aces don’t know they’re ace because noone ever told them it was a valid sexual orientation.
    b) They’re terribly confused about things like kissing
    c) They still want to date people because they really like them, or they want companionship and/or romance, and they secretly hope they will find someone who will be patient about sex (that’s what I used to tell myself: it’s not that I don’t want it, it’s just because I have… issues).

    I stopped dating very early on (I had a bad experience with it and I just didn’t have the motivation to try it again), but when I thought about dating, the idea of kissing was very problematic, because how do you kiss someone? I can’t think of a way to do it that doesn’t make me feel like I’m assaulting the other person.

    And he doesn’t have to even be asexual to have hang ups about kissing the LW. Maybe she needs to let him know she’s not a fragile flower who falls apart at the slightest touch. Some guys have it drilled into them that they have to be gentlemen so deeply that they’re scared of making any move.

    1. A very good point, too! On a somewhat related note, I’ve been hoping for a while now that there would be a Captain Awkward post addressing asexualty and dating.

      1. You and a lot of people are hoping for this post. I do not see myself writing about this at any point in the future, even though I get letters, because the answer is honestly “I dont know.”

        Coming out to your parents as asexual? I don’t know. Lots of good general “coming out” advice here.

        Want to date someone who is not asexual? I don’t know. I’ve been in relationships with mismatched libidos and they failed miserably. After that, I went on a few nice (no kissing) dates with someone who came out to me as asexual. I dumped him pretty much immediately, because how he described his feelings about sex (he would be willing to have sex sometimes to make me happy and have emotional closeness) did not match my feelings about sex and need to be desired. I can feel all asexual readers now saying “She thinks I’m undateable and unloveable.” No. I think you are undateable BY ME and it’s not something that I can or want to accomodate or overlook. I feel similarly about vegans – since cooking and eating are things you do all the time together, and I know that I will never be a vegan, should we really combine our cooking/eating stuff or should we just find people who gel with us? Is that really the post that people want? I’m the blogger of Love Does Not Conquer All, Sorry.

        Want to find other asexual people and form Boston Marriages? AWESOME, DO IT. How? I don’t know. Where? I don’t know.

        I know s.e. smith writes about this stuff sometimes and is generally a great writer you should read?

        If someone wants to take a crack at a guest-post, please email me.

        1. “I’m the blogger of Love Does Not Conquer All, Sorry.”

          That is one of the things I love most about this blog.

        2. Thanks for the reply, Captain! I totally get what you’re saying. Sometimes I wonder if asexuality is a thing that describes me, and if I want it to be, but honestly usually I don’t worry about it. To me, my asexual tendencies (or low sex drive) just ends up just being A Thing I Bring To Relationships. If the other person is into that and can navigate what I need without denying themself happiness or whatever, cool. We’ll see where that goes. If not, they’re not, and I wouldn’t want that for me OR them.

          Granted, I don’t date much, so I haven’t had a lot of opportunity to try this out in practice.

          1. There are so many reasons you could be experiencing low libido. Are you a dude? Have you had your testosterone levels tested?

            And, I mean, that’s all you can do with dating (see how it goes) no matter who you are and how you skew.

  9. Me and my boyfriend went to three mostly asexual (as in, not in any way sexual) dates. I was thinking that it was weird, especially that at least once or twice the kiss seemed like a natural way to go.

    So, the fourth date, we went to a club, and there I had the best kiss in my life (well, and the first one). So, if you want to kiss him, do it! But also don’t think that if he hasn’t kissed you yet, he won’t (or that you’re not kiss-worthy). My boyfriend then confessed me that he wanted to create the right atmosphere and didn’t want to rush things with me by asking me awkwardly if I want to be kissed.

    1. “by asking me awkwardly if I want to be kissed.”

      A lot of people think it’s awkward to ask/be asked to be kissed, and I have a hard time understanding it. I’ve had several dudes ask if they could kiss me (with a range of social skills) and it’s been sexy, flirty, terrifying (oh god I really like you), confusing (huh, I haven’t decided if I like you or not yet), and sometimes really sweet, but never awkward. It seems to me that, if anything, by asking you are actually saving yourself the potential Extremely Awkward Dodged Kiss, or a potential I-Don’t-Want-To-Kiss-Back-But-If-I-Don’t-It’s-Awkward-HELP – both of which, I think, are worse than “Thanks, but I’m not feeling it”?

      But I seem to be in the minority. Someone shed light?

  10. In my lifetime as a dude I have gotten to the kissing stage with seven ladies. Twice it was a mutual we-both-see-where-this-is-going thing. Four times she just grabbed me and kissed me. And once she basically said “I want to kiss you but I have this mental block about making the first move so you need to kiss me now.” Those were all good! And would you really want to get involved with a guy who was so hung up on traditional roles that he’d freak out if you were the one who initiated the first kiss? If *you* feel ready to move to the kissing stage, you should go for it. Tell him “hey, I like you a lot, can we kiss?” The worst that can happen is he’ll say “sorry, I don’t like you that way,” and then you can move on with your affections elsewhere.

  11. My beloved doesn’t make the first move. Ever. Since we started as farmville friends who actually talked to each other, and emailed more and more over a year of getting to know each other, I got to hear all about his many dates with a woman he liked which SEEMED to be dates, but nothing ever HAPPENED (and of course my response was “she’s waiting for you to kiss HER!)

    But at least I knew what to do when I got him alone :D.

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