new york dating tips: practice, practice, practice

[just a note: this one kind of got away from me, so forgive me if it makes little-to-no sense. I'll come up with one that's more coherent soon.]

This article popped up in my RSS feed a few days ago via The Gloss, with a recently engaged businesswoman talking about what she's learned from a life of dating (takeaway: stop wasting valuable business time worrying about dating, you could be using that mental energy to be [partner] at your [firm] by 28 instead). It's a good article and totally worth reading, but the bit in the beginning about Chuck E. Cheeze got me thinking about my own nascent dating history.

My first ever romantic entanglement was conducted largely via MSN Instant Messenger and a dial-up modem, with some boy whose name I no longer remember, but I know it was something sort of interesting, like Gideon or something like that. We told each other we liked each other on IM, but not with emoticons, because I was above emoticons then. We decided to meet in the library before first period (this was exciting in part because it was very early in seventh grade, and I was still super stoked on having seven different classes in one day).

On the appointed day, I took my male best friend with me for moral support and met up with Gideon-or-something. We stared at each other for about a minute, and then I think I giggled and ran away. It was a torrid affair. (By which I mean, I'm pretty sure that was the end of it.)

But then, later, on MSN, again, because I never learn, I think I asked this same boy why things weren't working out. And by "asked," I mean "interrogated about my shortcomings as a romantic partner." If you're wondering why I said I "think" I did this, and then got weirdly specific about what I asked, that would be because I repeated this process several times over the years.

So my message today, dear readers, is this:

Learn from your goddamn mistakes already.

By that, I really, really don't mean, interrogate people as you're breaking up to critique your performance. I mean, figure out after maybe the first time you do that that perhaps you would be better off not making people cry and then asking them to give you tips on picking up new people.

I've spent the majority of my dating life under the delusion that there's a right way to date. I thought that if I dug through the ruins of an old relationship, I would find the one thing that was going wrong, and all future relationships would be cupcakes and sunshine. Basically, I thought I should be working both sides of the relationship, with the other person there for... I'm not sure what.

To be fair, though, my biggest dating issue isn't that I ask people what happened, because I've found that, with a more grown-up voice and more distance, the "what went wrong?" conversation can actually be really great. And sometimes that can lead to getting back together. If you're me, it almost always does.

I was at my worst in high school - one guy and I got together and broke up once a semester, every semester, for three years. I interspersed those, of course, with re-dating other people I'd already had ruinous relationship explosions with. It's not even that I was just repeating bad relationship patterns. I was repeating bad relationship patterns with the same people. Over and over and over again.

Right now, I'm pretty single. I've had a few promising dates and even one or two second and third dates in the last almost-year since splitting up with E for good (at which point we had already broken up and gotten back together at least once and up to three times before, depending on how you count it). And, as with every other time I've been pretty single for a bit of a while, I start thinking back on my exes.

"That subway musician!" I think. "He only threw up on my bed the one time. I'll just look at his Facebook this one time. Looks like he's still busking for a living... Well, that's commitment!"

I then mention this to my best friend, who (quite rightly) tells me to stop being stupid.

"What about that girl I met that one time at that club?" I think. "Sure, I don't know her name or her number or really remember much about her, but I should look for her! Or that asshole who was so full of himself and has a girlfriend now..."

This is never a good idea.

I'm really trying to wean myself from the concept that I just sped through dating someone too quickly and that if I gave them another chance, we could really work out! I date most people in about three-tenths of a second and then declare, loudly and repeatedly, to everyone I know, why it didn't work out.

And then, six months or a year later, I go try to win them back.

Anyway, my point is this - if you're having problems with dating people, for whatever reason, and it's starting to seem like there are no people left in New York you haven't already dated, write down all the things that went wrong with various people. Sometimes, no, it wasn't your fault - the girl who got so wasted on your first date that she threw up on your shoes probably has her own issues - but you're going to find some common thread that you can start to examine.

I'm not saying there's something wrong with you. I'm saying that maybe you're ignoring an easy-to-spot pattern.

And when you spot it, and brightly declare to your friends that you've had this epiphany, they're all going to stare at you blankly and say, "You mean, you didn't know you did that?"

And you'll say, "Nope."