I keep falling for girls with boyfriends.

I have been single for several years and would like to be in a relationship. I meet a fair amount of girls in regular life activities, but very few are single/available. There have been three times in the past several years that I’ve met someone (though a friend, work, or relative) that I’ve really connected with. I find this doesn’t happen very often, so I pay attention when it does. But these three were all with someone else at the time we met. Because these girls were taken, I did and said nothing. I believe very much in fidelity and propriety. Unfortunately, by the time I heard that these girls were broken up with their significant others, they had already started dating other people.

I am now in that situation again, where I’m interested in someone who has a boyfriend. I am fairly sure she is somewhat interested in me. There’s just a vibe there I don’t experience very often. We’ve never yet done anything outside of a group, so I asked her to dinner, and she readily accepted. I don’t know what his status is with her boyfriend. If I do what I normally do, we’ll just continue to have a nice, friendly rapport, and if history holds, I’ll soon hear that she’s broken up with the boyfriend and is with someone else, and I’ve missed my opportunity. Is there any way to let her know that, should she become available, I’m interested, without sounding creepy and ruining the friendship? If so, I’d like to do that thing. I missed out because of my silence before, but I also want to be appropriate.

The creepy train has already left the station, and you, my friend, are the conductor.

You keep falling for girls who have boyfriends, and now you’re asking them out to dinner in order to plant the seed that you’d like to get in their pants should their pants become available to be gotten into in the near future. Not only are you setting yourself up for disaster, you’re being creepy by asking out someone else’s girlfriend. Even if she says yes, isn’t there some kind of unwritten rule that prohibits moving in on a friend’s girlfriend?

(Is this where the phrase “man code” would be appropriate? I hate that phrase–it’s so dumb–but it probably applies in this situation.)

I think it’s no accident that you keep falling for girls who already have boyfriends, and I think asking them out under the guise of being friends, when you’re secretly on a date, is weird. Stop being weird. Your weirdness is probably the reason why you get rejected by girls, and all that rejection is probably why you’re gun-shy about asking girls out, which is probably why you go for ones who aren’t available, so when it ends up not working, you have a reason other than your weirdness to point to for the fact that it didn’t work out.

Don’t get crushes on girls who have boyfriends. Get crushes on girls who don’t have boyfriends, and ask them out.

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