Helping a brother out.

Captain Cthulhu

Alright guys I need some help. My roommate right now is a super great guy. He's definitely my best friend in the Seattle area. He lives in a two bedroom with my girlfriend and I, and between seeing the two of us together all the time and Valentine's Day, I think his singleness is starting to get to him. The poor guy has been engaged twice, but ultimately fucked over by both girls and now I think he just feels like they're not worth the trouble. However, I can tell that in the short term, he really just wants someone to be with. Plus, he's 29 and though he has a fine job, he doesn't have a lot going on, aside from being a very talented, aspiring screen writer.

My point in all this is that I know that if he were to meet a girl right now that he thought was cool and attractive and fun to be around, he would just be way happier. So I've been trying to help him out without being weird. I'll send him Craigslist personal ads that look like they're up his alley once in a while, try to make sure some of my girlfriend's single friends hang out with all of us as much as possible and things like that but it's just not working. He's really sort of internally self-deprecating, I think. You know, in the way that he sees a girl he's interested in and just thinks "oh there's no way she'd be into me." and because of that, girls just don't notice him.

Anyway, anyone have any good ideas for really helping him out and getting him out there to meet some people?

MegaMan001

Can I ask for any more info, such as - how long ago was the last post-engagement breakup? I can't imagine that is easy to get over - and he may just not be ready? I think you're going great so far, well minus the Craig's List ads (I think that stuff is kind of out there, but maybe it's just not my cup of tea).

Have you tried building him up? Trying to get his confidence back by telling him all of his good qualities (maybe your girlfriend could help too?) I don't think he has a shot with pretty much any girl without the confidence to back it up.

Captain Cthulhu

I know it's been at least a year since his last engagement break up, or girlfriend of any kind for that matter, since it all occurred while he was living in pennsylvania and he's been in Seattle for a year. Craigslist ads can be a little out there, but there are a lot of good ones too, so I make sure to be his filter since it's easy to get discouraged when you see all the shitty ones up there. There are a lot of nice young professionals who post there because they just don't have a lot of time to get out and meet people and the bars aren't really their seen.

Honestly i feel like we've already made big strides in his confidence. He looks way better than he used to as far as how he dresses and what not. Maybe that's just from hanging out with two people who care way too much about their appearance but whatever the case I think he feels like he looks pretty good lately.

I just have a hard time giving him advice, you know? My way of meeting girls is to just go out, get drunk take 'em home and if they're not annoying or ugly as hell in the morning, maybe give them a call again later.

MegaMan001

Hmm, it doesn't sound like he's on board to make the first move - do you know if any of your girlfriend's single friends are interested in him? He may be more receptive to not making the first move, which has the added bonus of improving his self confidence once he sees a girl interested in him.

I hate to say it, but I'm not sure if there is a lot you can do. Ultimately the final decision is his if he wants to 'get back out there' or not.