I got out of a three-year relationship about two years ago. I have since dated half of LA. I'm getting wary of dating. Rarely have I been on a date where both of us liked the other — either I get interested or the guy does — and rejecting someone is about as much fun as being rejected.
I am starting to see a pattern: the guys will come on strong and chase me until I resist and when I kind of seem to get interested, the guys just vanish. Whether I tell them I'm interested or not interested — they vanish. I'm at a point where I'm too scared of going on dates for fear I'm going to scare people away. What do I do?
— Almost Too Scared to Date
To hear what a lawyer has to say,
Dear Too Scared,
Your situation is all-too-common among both sexes in the dysfunctional modern dating pool. Though I'm happily married now, I can confirm from very recent experience in the land of lovelorn singlehood that this dynamic/syndrome you are describing likely has less to do with your particular approach and more with your commitment to the idea of DATING with a capital "D."
There's something about the whole ritual, with all of its attendant expectations and conventions that seems to encourage a "chase is better than the catch" mentality among those who abide strictly by its tired protocols. More importantly, my experience with serial DATERS is that they often tend to be looking for the next best thing as a matter of course. They're just DATING with an idle hope that maybe it will just click with someone. But a DATE, in my experience, is a pretty lousy forum for actually getting to know someone and to see if you have actual compatibility, mutual attraction and chemistry.
My main piece of advice, therefore, would be to modify your expectations about what it is that you're doing, and to try to look for Mr. Right with a changed modality. If you are looking for a DATE, you are ultimately hoping to find someone to offer you love, companionship, nooky and sexual fulfillment, support, trust, entertainment, and everything else that comes along with finding someone awesome to share the world with, but much later and down the line, after you have made sure that he meets the sniff test and that you enjoy being with him. These are all things you can explore with guys in different social contexts that aren't so freighted with expectations, insecurity, performance anxiety, and all-around awkwardness as with the dreaded DATE.
So the approach, which is a tired cliché of the syndicated advice columnist for a reason: get involved with a group of people who share your interest in something (music, arts, book group, hiking club, discussion forum, team sport). Join an organized activity of like-minded people. And start hanging out with this group more and more (assuming they're not a bunch of weirdos and misfits that you don't enjoy spending time with).
See if there isn't someone in this broader group that you start to establish a friendship or rapport with (or who you find yourself attracted to, or scoping, or who seems to be attracted to or scoping you). And try as much as possible to avoid thinking of this person as a potential DATE, but rather, as a potential COMPANION (we'll leave it ambiguous for now).
Next, see if you can start to modulate your contact with this potential COMPANION. Maybe you invite him to some other group activity that you participate in. Maybe a party, or a BBQ, or whatever. Seth Rogen's character in Superbad might suggest inviting him to a pumpkin patch, but you get the idea.
You're ramping up towards an outing that we might typically call a DATE, but while you're at it, you're gathering all sorts of intel about this fellow, his likes, his dislikes, if he listens to cool music or butt rock like Nickelback and Hinder, whether he's more country or more rock and roll, if he's funny without trying to be (DATES are a notoriously embarrassing forum for us guys to try too hard to be funny, and enduring a DATE can often feel like watching some stand-up also-ran on Comedy Central).
Finally, if you are still interested in this COMPANION-cum-DATE, you'll identify an opportunity for just you and he to go do something together. If you can find something in the context of your initial meeting (say you are in that hiking club, then you suggest heading out to somewhere cool for a walk). You are making that DATE move, but in that context, it may feel a little less DATEY.
Significantly, you have already been around this person enough that, if he is interested, you don't need to use the awkward format of the DATE to find out stuff about the guy. You already found out all that stuff at the pumpkin patch. And if he has come along on the hike and made it through the preliminaries, one assumes, you may just find yourself a little more in sync, and less wary of one another. Because a DATE automatically has low expectations.
An ambiguous outing that feels less like a DATE and more like two people who are starting to enjoy spending time together? It's a space that you're likely to be much more comfortable with, and, just maybe, is less likely to generate that weird "catch me if you can" vibe that seems so endemic to DATING.
Best of luck in any case,