Reader Question #3: A shy guy caught my eye.

Dear Captain Awkward:

There’s this boy.  He’s cute.  He’s also super-reserved.  Do you have advice on making a connection with incredibly reserved, hard-to-read people? I am a lady, for clarification purposes.

If you met him in a karaoke bar, your way is clear:  Sing this song and then buy him a drink.

I’m guessing that you did not meet in a karaoke bar.  And that possibly if you sang this song he would not know that you were singing about him, or if he did he would be terribly self-conscious and his ears would go all pink in that way you like, but you would be no closer to actually, um, dating.

There is no one right way to approach someone you are interested in, and a lot of wrong ways.  Your question makes me overjoyed for two reasons.  First, because most dating advice in the world assumes that it is the man’s job to approach women and the woman’s job to make herself approachable.  Men=Agents.  Women= Objects.  Gross.  Second because it is possibly my destiny to create a dating guide for people who are geeky and unconfident but really sexy and cool once you get to know them.  Since we still have ten good years before the robot ladies replace us, let me get on that.

I think I might be the person for this job.  Because:

  1. I am geeky and not particularly conventionally pretty.
  2. I am terrible at both flirting and noticing when someone is flirting with me.
  3. Yet I have somehow dated a lot, both successfully and unsuccessfully.  And by a lot, I mean A LOT.
  4. Since I have no ability to flirt or have sexy banter of any kind, my approach basically boils down to “We’re both humans, let’s talk about stuff that interests us, and if that’s fun, let’s keep doing that until making out is either on like Donkey Kong or clearly not in the cards, in which case, friends?”

Believe me, I was not always this cool.  My approach, circa 1988-1998, went more like this:

  1. I like you.
  2. I am filled with SHAME, CONFUSION, and LUST.
  3. So, when you are nearby, I will ignore you!  But in a very obvious way!  Or I will pick an argument with you about something stupid!  And you will somehow know that means that I like you!
  4. I will become overly invested and have an entire relationship with the version of you I constructed in my head.  We will have long conversations, that Head-You and I, until one day it becomes too much and I must relieve the pressure–
  5. By cornering you and blurting out my feelings, or worse, writing you a letter that lays out my feelings and a thorough and airtight case for why we should be together.
  6. And then giving you that letter.  Slipped into your locker at school, or in one case (EEK!) having your roommate lay it on your pillow.

And before you go “Oh, god, are you a crazy person?  Who acts like that?” (Which, dude, I know, and it’s possible that some of those letters are still out there and someday I’ll be, I don’t know, accepting an Academy Award for Best Adapted Screenplay, and some dude I had a crush on in 9th grade will be like “Hey internet, here’s the obsessive stalker mash note she snuck into my Latin book one time!”), I’ll tell you who acts like that.

Mr. Darcy: Lord of the Dorks

Fitzwilliam Fucking Darcy, that’s who acts like that.  Only the supposedly totally dreamy main character of what became the boilerplate for every romantic comedy ever.  Let’s review:

  1. Creepy staring?  Check.  To the point where my friends and I refer to it as “Firthing,” as in, “And then he sat down at the next table, but I could tell he was still totally Firthing me, so I had to leave.”
  2. Becoming tongue-tied when the object of affection is close by, and masking emotions by either studiously ignoring or acting like a dick?  Check.
  3. Becoming overly invested in the relationship, where a couple of stilted conversations + dancing that one time = WE HAVE A MEANINGFUL CONNECTION? Check.
  4. Cornering the person and vomiting out your feelings?  Check.
  5. Putting it all in writing?  Yeah, that too.

Let’s watch a scene, shall we?


So what’s the right way?  Well, you obviously know this dude from somewhere, so you have opportunity to interact with him in some kind of safe, non-threatening way.  That’s good.

What I’d suggest, is, just talk to him.  Soon – don’t get overly invested in the idea of what interacting with him might be like.  Interact.  About stuff you’re (hopefully mutually) interested in.  And see what happens.

Dating Mad Lib

“Hi, I’ve seen you here a few times.  I really like _______ (something you are wearing, reading, doing, said).  My name is ________ (your name).  ___________(a question)?”

Now, you’re not delivering this like a weird rehearsed speech.  I mean, there will be pauses and responses from the other person, right?  But it’s a structure that you can adapt in many ways.

“Hi, I’ve seen you here (in the Medieval Manuscript collection of the library) a few times.  I really like your antique fountain pen.  Where did you buy it?”

“Hi, I really liked that question you asked in class today.  Have you done the reading for next week yet?”

This isn’t just for making a romantic connection, this is how you approach pretty much anyone you want to meet.  Hello, my name is + a compliment + a question.

Then I think the answer is to see where the interaction goes and stay as much as possible in the present moment.  By that I mean, pay attention to his responses.  Does he smile?  Does he keep the conversation going?  Even very reserved people will light up when they are genuinely engaged. With someone reserved, it might take a few interactions for something to click, so keep things short and light and be ready to politely withdraw.  The next time you run into him, see if maybe he says hello and smiles at you, and continue on as before.

I also mean, pay attention to your own responses.  When you’re crushing on the shy, reserved guy it’s totally easy to project all kinds of things onto the surface.  You don’t know what’s underneath, so (in your dirty lustful imagination) it’s all terribly complex and interesting.  So now that you’re having a conversation, is it interesting?  Are you enjoying yourself?  Is he as cool in person as he was in your imagination?  Do you feel safe and comfortable?  Are you still attracted?

You can’t control whether someone will like you. This is scary, especially there is an entire industry devoted to the question “What products can I buy to guarantee that I’ll be pretty enough that men will like me?” that has brainwashed us from birth.  (Answer:  Not Lip Stain.)   This is also incredibly freeing.  You can’t control whether someone will like you, so focus instead on your own experience and desires and use your interactions to figure out if you like him.

After you’ve had enough pleasant interactions that seem enjoyable to both parties, take the plunge:

“I really enjoy talking with you.  Would you like to grab dinner with me sometime?”  And then see what happens.  He could say no.  That’s disappointing, sure.  But not the end of the world.  He could say yes.  He could say yes but not realize that it’s a Date-date and you could get endlessly stuck in the Friend Zone, but that’s another post for another day.

So, to sum up, allow me to lay out a few of Captain Awkward’s Rules for Geek Dating, which should work for geeks of all genders:

  1. The other person is just a human, so talk to him like any other human you find interesting and wish to meet.
  2. Do it sooner rather than later, before you get too caught up in a fantasy or invested in the outcome.
  3. Nobody owes you time or affection, so don’t approach dating with a sense of entitlement.
  4. Be cool with rejection.
  5. You can’t control whether someone will like you, so focus on your own desires.
  6. Listen to the other person – pay attention to the actual interaction that is taking place and not the one in your head.
  7. Don’t date anyone who isn’t as cool as your friends.

24 thoughts on “Reader Question #3: A shy guy caught my eye.

  1. Thanks, Captain! I realized my question did not include the fact that I am rather shy myself in these situations, but I am totally relieved to see that I feel capable of putting most of this plan into action! Hurrah for suggestions for awkward geeks! (Actually taking the plunge and asking him out to dinner sounds slightly more unpleasant than having a giant beaky squid attach itself to my face, but baby steps!)

    1. Oh no, Giant Squid on Face!

      Trust me on this: If things are unfolding as they should, the dinner request (or coffee, or a movie, or a concert, or whatever) will come as a natural progression of an enjoyable conversation and it won’t be that weird.

      Also, I think every happy couple has a moment a few months in where they lie in bed together and play the “When did you first like me?” game and confess all the awkward moments and worries and hopes and it is delicious and great.

      1. Er. I have not had the courage to attach any squids to my face, but I have cunning plans to socialize with him more? Really! Cunning plans! Seriously, some more socializing has happened in the meantime, some of it fairly promising, and I think we are getting to know each other better, but it is going verrrrry slooooooowly and I have as yet no clues as to whether this person would ever be interested in me. I will remember to update comments in a month or two, though!

      2. uuuuuuuuuuuurgh. OK, here is your 6 month update.

        Talking? Check. Hanging out? Check. Becoming friend-ish? Possibly even friends? Check.

        Having the courage to ask him on a date sometime as a natural progression of things? Not check. I am REALLY REALLY awkwardly cowardly about this sort of thing, and I think I am getting so desperately crushy that I will maybe just go for it, but perhaps I’ve let it go too long and I care too much and now I will be super-awkward and muck it up? Also, is there some weird friend-zone where now that we ARE friends I’m not allowed to ask him out? I don’t even know. And we see each other regularly, so there would be subsequent awkwardness.

        Halp. Getting to know him better through various social situations involved all the emotional spoons I have. Giant Squid on Face has potentially gotten even gianter. Help me not fear the Squid!

        1. Thanks for the update. You know what I’m going to say, right?

          Here’s your script:

          “I love hanging out with you, and I don’t want to make it weird by asking this, but would you ever want to go on a date?”

          Then you listen to what he says.

          If yes, GO ON DATE.

          If he says “no, because blah blah blah” you say “Okay, sorry to hear that obviously, but I hope you don’t mind that I asked.”

          Then you NEVER SPEAK OF IT AGAIN and all will be well between you.

          1. OK THANK YOU I WILL TRY.

            I did know what you were going to say, but I kind of need all the pep talk I can get at the moment in order to make it happen!

          2. I just asked him out and he said no. 😦 Time to put on the big-girl pants and work hard at being a friend!

  2. Word to all of this. Darcy is a DORK, people you want to date are still people, and no one knows what’s happening in your head until you SAY IT OUT LOUD. Rock on, Captain. Rock. On.

    1. I tried a different brand that sucked all moisture from the lower half of my face so gruesomely that if I wore it into your house, you would be within your rights to think that the Zombie Apocalypse had started and murder me to save your own life.

  3. I would also add — although I know this is obvious — that electronic communication is the shy person’s friend. My spouse and I would not be together today if he didn’t have a way to ask me out that didn’t allow him to escape the terrible possibility that I might say no TO HIS FACE.

    So if things are going haltingly in conversation, but you think there’s something there, maybe find a plausible excuse to swap email addresses or texting numbers? Some people are just better in that format.

    Don’t worry it doesn’t last–13 years into the marriage, we have lovely in-person conversations.

    1. Oh yes, this is beautiful advice! I think that internet dating has become so common that it was kind of exciting for the letter writer to meet someone NOT online, but it’s common for a reason.

  4. Nothing contributory below, just adulation and identification!

    Thank you for linking back to this in your Blogaversary post so that I could zip right to it and start formulating ways to start a Church of the Awesome Captain.

    My locker-dropped letters were works of art that will damn me one day. Woe betide the Firthiest of them all!

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