Dating Confessions

Confession: I’m 25, and until recently, I hadn’t been on a real first date.



Let’s take a step back. Obviously I’ve been on dates, but always dates with an already-boyfriend. The last time I was single was in college, so people didn’t “date” so much as “meet up at parties and/or after class” (or the dining hall, if you were feeling fancy). Plus, up until last fall, I was under the assumption I’d never have to navigate the tumultuous world of getting-to-know-you dating in my adult life. Mentally checking out of the single scene in 2010 means I don’t understand online dating (e.g. have actually asked someone “What’s a Tinder?”), social media etiquette (exactly how much do I tell them about my extensive Facebook stalking skills?) or rules about contacting each other (I’m told there is such a thing as too many emojis). And that’s IF you meet someone you even want to date, a tall order considering that it seemed I only met people after 2 a.m. with beer spilled somewhere on-or-around me. I wasn’t even sure if people just happened to meet one day and exchange numbers anymore, or if all the good “how did you meet?” stories were reduced to “a bar” or “an app.”

These are my confeeessiooons

These are my confeeessiooons

So imagine my surprise when an actual chance meeting one weekend afternoon, followed by a week of casual texting, led to plans on a recent weeknight. I suggested tapas, largely for two reasons: one, there’s a place I love in the Flatiron that was easy for both of us via metro; and two: tapas strike me as the perfect date food. Is the date going well? Keep ordering food. Not so much? Order a small plate and then pretend you need to get home to the cat. Preparations on my end were… interesting. My lovely friend M and I spent the night before creating our Very Important Questions List, which consisted of such gems as “Do you know who Alton Brown is?” and “How do you feel about drunk brunch?” My father offered me some words of wisdom, to the tune of “uuuh save the details for your mother” and “he better be a football fan” (family priorities). I realized while in the office that I’d accidentally worn a sweater with visible coffee stains and forgot to bring flats for the rain. And then, in a true space cadet moment, I sent him the wrong address. So all in all, I was pretty much nailing this “date” thing before it even started.

Everyone has a different moment where you realize you could be ready to put yourself out there, whether it’s just a date or the start of something more. It doesn’t matter if you’ve been single for years or if you’re cautiously starting over. There’s not much to lose in giving someone a few hours of your weeknight, talking about yourself and hoping it goes well. Worst case s… well okay worst case scenario they turn out to be a serial killer or a Patriots fan or something else unforgivable, but relative worst case scenario, you walk away from the night with a good story and comfortable knowledge it isn’t going to work out.

Best case scenario? Not sure I can really speak to that, given my limited experience. But somewhere high on that spectrum there’s a night where one conversation turns into another, turns into another round, turns into another place, turns into almost midnight, still laughing and desperately wishing you didn’t need to leave.


One thought on “Dating Confessions

  1. Pingback: Chronicle Q&A | Chronicle of a 20-whatever

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