#377: Ask her out, already. You can do it.

Dear Captain Awkward,

I feel this is essentially a non-question, and you will just tell me to “use my words”. But I think I need to hear it, so bear with me please.

I am 19 years old, and attending university. All my life I have been a nerd of the science/tech variety, but I never had any problems navigating social events. I am rather outgoing, and generally not awkward, but rather perceived as witty (if a bit snarky), knowledgeable and fun to be around. Yet up until now never did I draw a girl’s attention towards me (except for being interested in friendship, which is not a bad thing in itself) – and I did not really try to because those I were into were in relationships already. But lately there is this girl in my social circle I keep running into at parties. She is beautiful, with a sense of humor I can connect with and a relaxed attitude to life that mirrors my own. In short, I like her very much. After we met a few times, and had quite a great time talking and drinking and just being there with the others, at one occasion she kissed me. We made out a bit further on that evening, but a mutual aquaintance began drunkenly insulting her (erm…don’t ask, he is another story) whenever no one else was listening, so she left. And this is where the awkwardness begins: We couldn’t see each other for over a month, for reasons none of us could influence, and when we met again, both of us behaved as if nothing happened (I had convinced myself she wasn’t really into me for whatever reason, and whatever she thought, I don’t know) This continued until recently, where we walked along a street at night and she just turned to me and kissed me again. And again. And for the rest of the night (which continued through several bars) we made out and talked and just seemed to everyone watching like a newly formed couple (according to my friends observations, at least). I still didn’t know what to think of this, and when we met again at a party a few days later, the same thing happened. I sat beside her, she leaned against me, and we kissed.

And since then, no communication whatsoever has been exchanged between us. It is a bit awkward, for I do not know her number (which she is reluctant to give out due to some quirk), but we can (and have in the past) chat on facebook. Every single thing (from “wanna meet sometime” to “I like you, do you want to go out next Friday”) sounds utterly dumb in my ears, and I cannot make myself send any message to her. Even the thought of it makes the butterflies in my intestines go rogue, and I sit hours in front of my computer just staring at the screen and trying to overcome this irrational barrier that holds me back.

Any advice for an unexperienced coward? (Note that I do not have any fear to contact other people, this just occurs whenever crushes or sex or romance enter into the equation)

Yours thankfully,
Irrational Anxiety

Oh, buddy. We got this.

Consider a few things for me:

1. What is the best thing that can happen here if you write to her? Answer: KISSPLOSIONS

2. What is the worst thing that can happen if you write to her? Answer: A pterodactyl swoops down from above, snatching her up, and cutting your doomed love short. Nuclear war and or other apocalypse. Let me point out that these unlikely events would in no way be caused by your contacting her, they would simply be “I wanted to go out with you but oh shit, apocalypse! If we both survive I’m definitely taking you to dinner, though” situations.

3. What is the worst thing that is likely to happen if you write to her? Answer: She had fun kissing you but is over it now. Which, you could totally bounce back from if this were the case, and knowing would at least get you away from staring at a blank screen feeling like a jerk.

So, armed with the worst- and best-case scenarios, email this lady! She is waiting for you to email. She is wondering aloud to her friends why you don’t email. She put her face on your face more than once. Her work here is done. It is definitely your turn.

Let’s Cyrano Β your de Bergerac:

Dear _____,

Do you have some time this weekend to go on a date with me? I would really love to see you.

One salutation and two short sentences stand between you and the possibility of something amazing. Send them! You can do it.

71 thoughts on “#377: Ask her out, already. You can do it.

    1. I’m totally hearing Bela Karolyi in Atlanta in 1996 yelling at Kerri Strugg before her vault. πŸ˜€

      But yes! GO LW!!!!

  1. Doooo iiiiiiiit. Seriously, I was in a situation similar to this when I was a freshman in college, and even though we were clearly both interested in each other, he never asked me out. (I could have asked him, sure, but I’d made the last move, so in my mind it was his turn.) And eventually I got bored with waiting and ended up dating a skeevy grad student instead.

    Don’t let her date a skeevy grad student, LW. Just one facebook message from you could save her from this terrible fate.

  2. She totally wants to kiss you more. She is totally analyzing your lack of contact with her best friend right now.
    Also, I love how straightforward this.

    1. Yes, this. Because you know, fuck pterodactyls, but here is actually the Worst Thing that could happen if you don’t email her (with apologizes to CA for the kludgy format)


      Busy crowds with some flight announcements in the background, but not so busy that we can’t see an OLDER VERSION OF LW approaching, texting away on hir phone. LW looks up at a BEAUTIFUL GIRL walking past, looks down at hir phone, and does a double take.


      Excuse me! Are you Beautiful Girl?


      Yes, I– LW! Oh my god, it’s been years!


      Ten years. Wow. How are you–you look great! Oh wow, I’m sorry, that was rude.


      No, no it was….so, how are you?


      Oh, pretty good, I guess, I moved to the other coast, got a job, you know, the usual.


      Virgin Atlantic is now boarding at Gate 3 for departure to Kuala Lumpur.


      That’s my flight, I have to run.


      Oh. Well, sorry we didn’t have time, if you–

      BEAUTIFUL GIRL (urgently)

      Listen, I just wanted you to know, back when we were in college, I had a massive crush on you. I kind of threw myself at you, and you were so, well, you were so mature about it. I mean I kept jumping at you and kissing you! And even though you were totally not attracted to me at all, you were kind, and you didn’t let it mess up your friendship.




      I was a mess about it, you know, drama drama to my friends, WHY DOESN’T LW SAY SOMETHING? and my best friend finally sat me down and said, look, zie’s clearly not that into you, if you keep this up you’re going to ruin the friendship. And you never mocked me, or told me to take a hike, or did anything other than be kind and a real friend to me. That was the first time I’ve ever had somebody I had a crush on treat me that well.

      FOCUS and PAN on BEAUTIFUL GIRL’s hand as she’s talking; she’s wearing a bright gold wedding ring. We PULL BACK to LW as BEAUTIFUL GIRL startles hir with a chaste kiss on the cheek.


      Anyway, thank you.

      LW turns to watch as BEAUTIFUL GIRL hurries away through the airport terminal.

      1. Something inside of me just died right after reading this. In a good way. The scene was so vivid before my inner eye. My mind already knew that inaction is bad, but this just bypassed all thoughts and went straight to my heart. Thank you.

  3. LW, here is the email I wrote after very similar circumstances:

    Subject: So….

    I enjoyed hanging out with you this weekend, and would like to do it more.

    My unfortunate limitation right now is that I am unemployed. I hopefully will have income soon, but while I don’t, I am unable to spend money on non-necessary things. But if you have any ideas to get around this barrier, I am open to hearing them.


    It’s 2.75 years later and we’re engaged.
    Just write it. πŸ™‚

  4. LW, let me tell you. I’m over 10 years older than you, and I’ve only recently started getting up the guts to email people in a similar situation. I say “similar”, because, in the most recent case, there was no kissing beforehand or anything like that. Quite scary to email her! After a few days, I did. A short email asking her out.

    And she said no. And it felt great! Really! We quickly resolved that we’re still friends, and at least I can stop thinking about her in that way anymore. I cut it short way before it got to the obsession stage (which was my usual modus operandi for years), so now I just have an attractive friend who I don’t get to make out with (or, if I prefer, an attractive person-I-don’t-see-that-often). And this was likely the worst-case scenario! If I had known years ago how much better rejection feels than that build-up to the obsession stage and the constant wondering, I would’ve risked it a long time ago!

    And this is with someone who *didn’t* kiss me multiple times first. So your chances of that worst-case happening are much smaller than mine.

    Go for it, and good luck!

  5. KISS THE GIRL! Well, kiss her more! Seriously, this is as close as you’re ever going to get to a guaranteed ‘yes’ in this situation. Probably the only reason she hasn’t asked you out is the stupid thing where girls aren’t meant to ask guys out…which is ridiculous.

  6. Oh LW, you have a really easy and fun problem! To recap:

    -you met a girl you liked
    -you talked to the girl a bunch and liked her even more
    -the last several times you’ve seen girl, she has put her face on your face
    -you have a means of contacting the girl

    This is a recipe for win! I know that actually asking someone you like to go on a date is always a little nerve-wracking, but you literally could not be in a better position to take the plunge. You guys talk and laugh and cuddle! She keeps putting her face on your face! All signs are go!

    And if it helps, know that when someone likes you any words you use to ask them out are going to sound good and produce butterflies. I once had a crush ask to kiss me for the first time by saying “Gimme some sugar, baby” because we were watching Army of Darkness and Bruce Campbell had just said that line. That is, in the abstract, a REALLY DUMB LINE — but it was AWESOME when used by my crush.

    1. So true. My crush gave me a peck on the cheek at a pivotal juncture. I said “Can I have a proper kiss please?”.

      He loved it, but I cringe still.

    2. *wipes tear*

      That’s beautiful.

      My husband and I had our first kiss (and only my second ever) while watching Evil Dead 2, so that will always be the movie I have never really seen because we were too busy making out like crazed weasels, but I have fond memories of, nevertheless.

      To the LW: I’m a nerd/geek/dork, my husband’s a nerd/geek/dork. Nerd/geek/dork romance is a really beautiful thing. You must email this person! And email other people! And go on dates! (I mean, if you want to go on dates and meet people and maybe wind up with a partner, I don’t want to project all over your future.) But if you put yourself out there, you WILL have wonderful geektastic moments like this, and it will be ridiculawesome, and seriously, it’s worth the awkwardness.

      It sounds like you have a really good shot at getting to know this person better, and hey, there’s chemistry. Message them. None of what you said sounds dorky. “I liked the time we spent together. I’d like to spend more time with you. Maybe a date?” I’d be happy to get that message. Genuinely.

      Hit that send button! It only takes a second, and you can cringe and flail your hands around and screech like a pterodactyl all you want afterwards and at least she cannot see that. That’s what I do, and it helps ME.

  7. DO IT! She has totally placed the ball in ‘your court’ by making the first move last time you were hanging out together.

    One time I had some make-out fun with a boy.
    The next day he called me up awkwardly and asked if I wanted to see a mid-night showing of Blade-Runner (because he knew I loved that movie). The date was weird and super awkward, but long story short we are still having the make-outs. They are really nice.

  8. Oh, this poor woman! She has repeatedly crawled way out on the limb to let you know she likes you “that way,” and you’re leaving her stewing, wondering if you just kissed her because her face was in your way or whether you really like her, too! Sheesh, summon your gumption, don’t worry about the wording, and ask her out!

      1. Ahaha! “O great, someone’s face is in my way. Well, it looks like I’ll have to kiss my way out of another one!”

  9. When I was younger I used to get over the fear by being all cool and casual about things. Which isn’t advice for always – sometimes you have to let people see the real you. But for the purposes of a getting things started email, how about prefacing the Captain’s script with “Hey – it feels like about time I asked you out already.” Thus acknowledging previous kissing interaction but avoiding feelingsmail coming out too early.

    1. Ok so if I were the LW’s lady-friend and I put on my overthinking it hat* I might read this line as the LW feeling like he was *obliged* to ask me out because of the kissing thing. You don’t want someone feeling like they are only being asked out of duty.

      *LW you may be cool with this as your particular lady might not own an overthinking it hat. Alas many of us nerdy geeks have a whole collection of overthinking it hats.

      1. Totally agree that’s a risk, which is why I would only put it as a preface to the captain’s suggestion, which includes the all important ” I would love to see you” line for balance.

  10. You two talked, and she came back to talk to you some more. You two kissed, and she came back to kiss you some more. There was even time to think it over, and she still wanted to kiss you and talk to you. She likes you! She wants to kiss you! She’s waiting to hear from you! My hand is already in the air, waiting to give you the highest of fives. aYou can do it!

  11. I love you, all of you. You just gave me the right push to go and message her. (And @alphakitty, do not think that I have not also thought about how she must feel. Which only contributed more to my worries. I’m sorry πŸ˜‰ ) I’ll definitely tell you how it turns out. I needed some unrelated voice to tell me this, and you have done it so awesomely that I lack words for it. Thank you.

  12. It’s nice to see a fun one with easy answers! I’ll add to the “Go for it!” chorus.

    And don’t worry too much about how you go about saying things. When you’re really into someone, you don’t sit around nitpicking how they asked you out – you’re just glad they finally did!

  13. Realistically, the worst thing that can happen if you write her is “no more kissing.”

    The guaranteed thing that will happen if you don’t is “no more kissing.”


    1. Amen to that.

      And an addendum: even though you’ve got all these internet strangers invested in your story and rooting for you, SERIOUSLY DO NOT PUT PRESSURE ON YOURSELF. I would totally be sitting there right now like all “Jeez, Sadie, you’d better not screw this up or People Will Know.”

      Dude[ette], we will be here to high-five if it goes well… and to sympathize if it doesn’t. Just be your own cool self and… well, good luck. πŸ™‚

  14. Happy Ending Thursday! My new favorite holiday. (Although today is already Kraken Day…but then any day that ends with a giant cephalopod movie is a pretty good one, so it still works.)

  15. I have never ever ever initiated a kiss with someone unless I really liked him and wanted him to ask me out. She is waaaaaay into you, LW. Send that message, stat!

  16. As someone who has been asked out by many a nerdy dude in her day, I am going to give some unsolicited advice in case things end up going very well for you, which I hope it does!

    *clears throat*

    It is quite okay for you to “ask her out” over email/FB/IM/other technological implements right now, for a value of “ask her out” that means “make plans for a date.”

    If the date goes well and you go on more dates and you decide you wish for her to be your Official Girlfriend… it is NOT okay to “ask her out” over email for the value of “ask her out” that means “ask her if she wants to be your girlfriend”. The Becoming an Item talk needs to happen in person.

    You may not need this piece of advice, but I have been on the receiving end of this second one multiple times so apparently this is a common nerdy-dude misconception, so I just wanted to make sure it was all cleared up in advance.

    Report back to us!

    1. On a similar note: the general consensus here is that there’s a pretty good chance that she’s into you, so in the likely case that you get a positive response, awesome! Start getting psyched about the likely fun that you two will get to have soon, hanging and probably making out!

      But I’d recommend not starting to spend too much time daydreaming about her being your Official Girlfriend until you’ve actually had that first date or two and seen how they go. Going into them with the intention of having fun that night without the stress of it having to instantly Mean Something can make the dates themselves less stressful and more fun. Andfrankly, tthere’s a good chance that y’all will have fun for a few dates but not really feel it for a Serious Relationship… give yourself the opportunity to let yourselves both have a good time without Where Is This Going being the only thing in your head.

      Don’t get me wrong, if things continue to do well then get excited about becoming more official. But you don’t want to spend the week before your first “asked out” date thinking about wedding bells.

  17. I gotta know how this turns out. Though I fear my potential squeeing may destroy my computer monitor…..

  18. I have to recount my best friend’s tale of the “what’s the worst that can happen?” conversation he had with his uncle. I keep this story handy for just such occasions.

    BF: I want to ask this girl out, but I’m afraid to!
    Uncle: If you ask her out, what’s the worst thing that can happen?
    BF: She’ll say “no”?
    Uncle, No, the worst thing that can happen is that she pulls out a knife and stabs you in the chest. So if all she does is say “no” then you get to walk around all day saying “Hey, I cheated death!”

    1. I have a friend named Dave. He is awesome, and sometimes he gets emotionally worked up. When that happens, someone might ask him what’s the worst that will happen?

      Dave says, “Dingoes will eat my babies!”

      Confused, the person says, “But Dave, you don’t have any children.”

      And Dave looks at them intently and says: “Exactly.”

  19. since I’ve ripped off the commenting bandaid…

    this is so similar to how my partner & I got together that I just have to share that story (although because it hinges on a Wet Hot American Summer reference, people who aren’t fans of that movie might not even appreciate it).

    after some protracted plausible-deniability flirting, we’d finally done the make-out thing one night (er…morning, on a friend’s couch; long story), & then the next day ended up hanging out with mutual friends after a meeting we were all attending. I was walked home, got a kiss at the door, was happy.

    then, because I’m forward like that, I sent an email saying: “so, when do I get to see you again?” & the reply was: “anytime. dinner? literally anytime.”

    …that was more than 10 years ago, & the rest is history. πŸ™‚

    in conclusion (to echo what everyone else is saying): this is the most cut-&-dry “ask her out!” situation of all time, & I would be shocked if the response wasn’t positive.

  20. I was in a similar situation LW! And from the girl’s perspective, she’s totally waiting for your message, so wait to go for writing to her!

  21. For some reason, I have only just got around to reading this post, and now I must know what happened! I hope LW and his crush are too busy having KISSPLOSIONS to give an update to us Random Strangers on the Internet, but in case it didn’t go well, we’re here for you, LW!

    1. I have actually been checking back to see if LW commented, because of all the things to be invested in, I have chosen a complete stranger on the internet.

  22. Just so that you can be as tense as I am, I will tell you that it’s going to be this friday that we’ll go out. And I am already running around and screeching like a pterodactyl (to further strain an already overused simile) and driving my roommate crazy. If I don’t die of a heart attack, you will hear from me again πŸ˜‰


      also, deep breaths!

      also, just in case you’re dealing with your pterodactylity by reading comments, experience indicates that: the best thing to do if things are sooper awkward is be like “LOL ISN’T THIS AWKWARD”, and then go for a walk and more kisses or something.

      OMG I HOPE YOU ARE GONNA WEAR A SPIFFY TIE. (if appropriate.)

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