I’m early-thirties, single, good-looking, about to become fairly wealthy from a hot start-up.
I’m trying to break out of my pattern of relationships. Typically I’ll be single for a couple years, some girl that I’m not really into will express some interest and I’ll go on a date to be a good sport, if I’m lonely or desperate I’ll sleep with them and then find myself attached to someone I’m mostly bored by. Then I get sick of it and dump them and it’s a big mess.
It’s not that I can’t approach girls; I just never seem to meet any decent ones who are single. In fact, I can’t even recall the last time I met one. They all seem to have boyfriends — and hell, that makes perfect sense, why wouldn’t a cute, interesting chick have a boyfriend?
The only answer I can come up with is that such girls are /never/ single, they just date a guy until someone better comes along. A friend of mine called that “monkeys swing from trees.” If that’s the case, the only logical course of action is to go ahead and consider girls-with-boyfriends fair game. And that’s sleazy.
About to become wealthy, eh? Well then, your pattern of relationships is gonna change anyway, so I’ll go ahead and skip over this bland question and answer the one you’re guaranteed to have in about a year.
So yeah, instead of boring, not-quite-decent girls occasionally expressing interest in you, your dance card is about to be full of fascinating, attractive women who crave your attention.
Yes, it’s the money.
Your question will be, “How can I tell if they’re really interested in me as a person, and not just enamored with the lifestyle I can provide them?”
Judging by the way you already think of relationships, I can tell you’re already pretty terrified of this. Guys who are looking for a “decent” woman tend to have a massive madonna-whore complex, and when money gets thrown into the mix, it’s a recipe for an unhealthy dynamic.
The trick will be finding your equal, whatever that means to you. Stop looking for a decent girl, and start looking for your equal.
When you’re looking for a decent girl, you’re using an external set of criteria upon which to judge her character. When you’re looking for your equal, you’re using an internal set of criteria. It’s a subtle distinction, but it makes all the difference in the world.
Oh, and if she flinches at a pre-nup, run for the hills.