The Kind of Girl Who … asks out strangers right on the street

NTKOG #32: The kind of bold, vivacious creature who, standing on a street corner, catches the eye of a stranger, banters for a moment, then asks him out right then and there.

I am: shy. Deeply shy. Surely by now you all know that I’m an extreme introvert?

I am not: convinced I’ve ever even actually been on a date with a guy whom I hadn’t been seeing exclusively for at least several months.

The Scene: Wednesday after work, and after my hyper-uncouth spitting adventure, I was wandering around Harvard Square, trying to kill an hour before my creative writing class. I decided to cross the street and get a cupcake, and waited for a light, standing next to a tall, nice-looking Asian guy.

Also, for context, I was wearing my Alice-in-Wonderland dress, a light sweater and flipflops, and basically freezing my eyelashes off.

Stoplight Guy: Aren’t you cold in that?
TKOG: Yeah. But I just moved here from California, so I’m just pretending it’s an unseasonably cold summer day. In late September.
SG: Where in California? I’m from [Prestigious West Coast University's rival school].
TKOG: Oh, I went to Prestigious West Coast University. I guess we hate each other now. Where are you headed?
SG: Nowhere, really. You?
TKOG: I have an hour to kill before class; I was going to grab a coffee. Want to join me?

And guys! He absolutely said yes!!!

We found a cafe — where it transpired that neither of us actually drinks coffee — and both independently asked for the orders “for-here”. So no awkward-out escape hatch.

There was a moment in the line. I felt like I should pay for his order because I’d totally instigated the hang-out, but the line was confusing and I couldn’t find my wallet. At one point I asked if we were even in line, to which he responded: “Well, I am. And you’re with me.” in the sort of paternalistic way that I don’t really hate, and I resolved to pay for his drink, but then lost my nerve.

As we waited for our mugs o’ seasonal beverage, we talked about our academic and career trajectories. He’s currently pursuing a law degree from Hahvahd, but claimed he wants to retire early from corporate law to focus on oil painting. Whenever men say things like that, I wonder whether it is only what they think we want to hear, and if so, why the devil they think we want to hear it.

He was very frank about money — wanting to make it, and lots of it — in a way that, on paper, would have seemed crass. But I have a soft spot for men who are appallingly forthright with a hint of egotism. Similarly, he gave the obviously overworked barista a hard time about making him wait for his drink, and although I hated it, I kind of admired it.

We ended up sitting outside and talking intensely for about an hour. It was all the standard terrible first-date stuff (undergrad experiences, the weather, out-of-reach career fantasies), but done quite well. The conversation was mile-a-minute and clever. He did not make me laugh, of course — very few men do — but we enjoyed each other’s company. It was all the terrible first date conversation, true, but I felt we were working through it. I could see the first-date slipping into a second date with the same natural flow, but more off-the-wall, engaging, whimsical, real.

Then I mentioned growing up in Las Vegas, which is always a mistake: it always, always causes men to grow slimy and disrespectful, at least a little, even the nice ones (let alone barista beraters). I had mentioned not knowing Cambridge well, and we talked about finding a bar and going out for post-work drinks one day. But after the Vegas discussion: “Oh, when is your class over? We could just have drinks at your place…”

Sorry. Did I miss some sort of critical transition in the evening? We made tentative plans to see each other again for drinks (at a bar, not my apartment, obvi), exchanged information, then I had to book to my class.

The Verdict: I would absolutely, totally, 100% do this again! It comes off sounding a more negative experience than it was: to be fair, it was nearly entirely enjoyable, and only took on a weird tone right at the end.

As of right now, he has called a few times, but I keep missing his calls. I texted and he responded with a voicemail asking what I was up to (and for my blog address — whoops, shouldn’t have mentioned that). I think I’m going to ask him if he wants to grab drinks on Monday.

But truly, guys, it was totally pleasant and there was no awkward at all. If you’re reading this and you’re single, I totally encourage you to stop a stranger this weekend and ask them to hang out. Just try it! You’ll feel like a ballsier, better person. (Unless the person turns out to be a total sketchmonger…)

Tagged as: asking out stranger, awkward, conversation, date, dating, first date, harvard, las vegas, relationship, single, stranger, what happens in vegas apparently don't stay in vegas as random strangers often try to badger it out of you