Dear Captain Awkward,
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:
- I am geeky and not particularly conventionally pretty.
- I am terrible at both flirting and noticing when someone is flirting with me.
- Yet I have somehow dated a lot, both successfully and unsuccessfully. And by a lot, I mean A LOT.
- 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:
- I like you.
- I am filled with SHAME, CONFUSION, and LUST.
- 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!
- 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–
- 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.
- 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. Read More