DO THIS DON'T: Ask A Stranger On A Date (On Twitter, Even)

As women we’re conditioned to assume that if a man doesn’t immediately turn into a stumbling mess and/or brandish his phone number demanding a date, he’s probably not into you.
Publish date:
September 20, 2013
twitter, do this don't, ask him out, shy guys

I am blowing exactly no one’s mind by stating that the never-ending hangover of gender norms make hetero dating a little sticky. Who pays?* Who drives? Who is expected to plant the first kiss? But even getting to the point of “on a date” can get hung up in one big, really outdated factor: That women, generally, do not feel comfortable or compelled to make the first move. But they should! Because it works! Also, it’s kind of a nice thing to do.

My boyfriend loves to tell the story of how we met, in part because it is sweet and also because, as a relatively quiet and pretty shy fellow, being asked first (and kissed first) was super-novel. Because unlike women, who are used to attention -- a lot of it unwanted and problematic and often really emotionally burdensome and sometimes even dangerous -- most men don’t get noticed. Especially quiet guys.

The kind of guys who you see in bars and maybe even think are cute but don’t talk to. And they definitely don’t talk to you. They are not the men who come up and brazenly interrupt your happy hour with a friend with asinine, unwelcome conversation. They are also the men for whom sending the first OK Cupid message is really nerve-wracking and awful.

What happened was this: Two years ago, I was writing for a website and helping with the social aspect, and someone retweeted an article I’d written. I checked out his information and followed him because I don’t know why. Why does anyone follow anyway?

Anyway, he followed me back... and then emailed me. So I guess technically he kind of made the first-ish move beyond Twitter. But it wasn’t to ask me out, it was to ask a question about a job. We had a brief interaction. That was all. Then, for two years, we just quietly followed each other on Twitter. I was in a relationship. He was living in another city but eventually moved back. We were basically strangers.

But then, one day when I was single and still a little raw from a particularly painful breakup, one of his tweets caught my eye. And we started chatting. On Twitter.

“Um...have you ever flirted on Twitter?” I asked my co-worker. I was honestly a little baffled. It was fun and he was funny, and I was doing some online dating so I was used to messaging cutesy little things that are completely unimportant to relative strangers. But, I had to remind myself, this wasn’t that. This was just Twitter, which both he and I use for our jobs because we are internet people. How did I even know he was into it like I was into it?

Because, see, as women we’re conditioned to assume that if a man doesn’t immediately turn into a stumbling mess and/or brandish his phone number demanding a date, he’s probably not into it. Which I have been assured, over and over again by reliable, confirmed male humans, is not the case. Plenty of guys are into it, they just don’t want to invade your space. They don’t want to be the creeps that all of us encounter all the time.

So I screwed my digital courage to the sticking point and messaged him that we should continue the conversation in person. He accepted. And when we met, it turned out, we were unsure, but both hoping it was a date. At the end of the night, fearing an awkward, platonic hug on a street corner, I psyched myself up again and kissed him. It also helped that I had been drinking, but that’s beside the point.

That was months ago.

Now we are dating and we are quite fond of each other. And he has assured me that it never would’ve happened if I hadn’t sent that first message. Because he didn’t want to impose on my life. Because he’s kind of a decent dude like that.

Which isn’t to say that decent dudes, as a rule, don’t ask women out, or that the man making the first move automatically makes him a creep, because of course it doesn’t, and that would be a ludicrous double-standard. But a lot of men are just too shy or afraid of overstepping the boundary of respect to slide you, a female in whom they have already shown interest, that matchbook with a phone number on it.

All of this is to say: Do it! The guy on OKC who also spends his typical Friday night eating grilled cheese while watching Deep Space Nine? He may never message you -- but it’s cool because messaging goes both ways! So does real-life conversation! That cute guy who makes your coffee every morning who you have a great rapport with? Stop checking for the Missed Connection you’re sure is coming and ask him if he’d like to meet somewhere other than his place of work.

Might you get rejected? Maybe! Will it kill you? No! If anything, it will bring the genders ever so much closer to understanding each other. And also, you know, get you some. Which is worth it!

*You split it. Just do that thing. This actually should not be a question. You ate some food? Pay for that food.