So, I’m dating. It’s new and slow and fragile, and I don’t necessarily know where things are going, but there are a couple of people I’m seeing on an ongoing basis, and a handful more with explicit interest that just need the logistics hammered out, and some more than that where we’re still in the initial hey-you’re-hot dance. I’m not actually seeing a ton of people, but there’s enough activity that I could legitimately be said to be “dating”.

I’m sure I’ll have more on this later. However, one of the missions of this blog has been to record what I’m going through in order to have something to show to the next person who gets into an open relationship and then tries to figure out how to date from within it. So, I have a handful of things that I’ve learned and will impart here. I hesitate to call them “tips”, and they’re going to be slanted toward online dating just because that’s what I do. But with any luck, some of what I’ve learned will be useful to other people as they pick this stuff up.

I’m just going to dole them out one at a time; that both gives me more blog material and gives me a chance to go thoroughly over my thinking on each subject.

The first thing that I’ve learned, and that you can find everywhere but is still no help until you’ve experienced it, is that the only way to make yourself able to ask people out is to ask people out. You have to get used to the sensation. It’s a lot like sending out resumés, especially online; you invest yourself far too much in the first handful, and it feels like dying to even try. For a while after that it’s merely bad, and you’re okay unless you think about it. Eventually, though, after enough tries, you just inure yourself to the pain of being exposed like that, and you can forge ahead. It’s not, in my experience, rejection that’s awful; it’s that limbo between putting something out there and getting a response to it. At least, if you’re rejected, you can close that attempt out and move on.

It really does get better, though. Much, much better. Now, I can whip up a self-deprecating and witty e-mail that ends with a question about something in someone’s online profile with nary a thought. It’s become easy and routine to introduce myself, and that’s profound.

The immediate objection of a lot of (especially online, especially male) daters is that they go hunting for that ONE SPECIAL PERSON and then craft a personalized woo-packet for exactly their affections’ object. That’s an easy trap to fall into, but it’s bullshit. Unless you’re in the habit of dating only close friends, you simply don’t know someone when you ask them out. Your initial introduction, be it via e-mail or hitting on someone at a bar, is nothing more than an inquiry; you’re trying to draw their attention in the event that they are also interested. It’s only after that initial contact that one has a real stake in the outcome.

The lesson here, I guess, is twofold:

  • Just start asking people out, knowing that it will get better after a time.
  • Understand that asking someone out is nothing more than an introduction, and learn not to set too much store by it.

Ultimately, though, the only way to make the approach no longer feel like a big deal is to make the approach in the first place.


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