[PSV]

A friend of mine and his girlfriend recently broke up. I hadn't hung out with this friend for most of their relationship, up until maybe the last month or so. I've technically known his girlfriend (ex-, now) since middle school, but we had never really talked until we started all hanging out together. Just to get it out, I would most definitely be interested in this girl if she weren't involved with my friend in any way. Since that's not the case, I'm not even considering it. It's interesting, my last girlfriend was actually this same friend's ex as well. So pursuing anything with this new girl wouldn't exactly give me the best track record, I think.

I would actually really like these two to get back together. At the same time I don't, because I also really want my friend to gain some confidence in himself. He's incredibly paranoid about whatever this girl does now, and who she's with away from him (they still hang out all the time). I've been telling him it's really not his business, and he should be doing the same thing himself (having his own life). He's just so hung up on her that he doesn't really try to better himself at all, and it doesn't help that he's been generally apathetic and lazy about a lot of things since way before they were ever together.

I want them to get back together really just to appease his current unhappiness. I know that they wouldn't last though, unfortunately, if he doesn't change his general state of mind. And I feel like that can be said about future relationships he'll be in. But how am I supposed to talk to him about this without being a total dick?

On top of that, I kind of already feel like a dick. Pretty much ever since I went through puberty, I've never fully allowed myself to be friends with girls. I mean, I have been friends with the girlfriends of other friends', but in the way that I talked to them and interacted with them, I never fully let myself down. Just look at the what happened with my last girlfriend, as I said before. I feel kind of inconsiderate sometimes, but I just feel like I don't know how to act with girls in just a straight, friendly way. It seems like there always has to be a little flirtation. All this said though, I still have tons of trouble with shyness and talking to girls I don't know. Weird.

So this had led me to realize that I am way more of flirt than I have always thought. Which is, strangely, kind of motivating. Since I've always been so shy, I thought I didn't really know how to flirt, and I was too shy to practice on anyone. I was stuck.

In hindsight though, I've realized I've flirted with my friend's ex quite a bit, but like I said, I'm not thinking about making anything of it. And it hasn't been made into a big deal by any party in this situation, friend included. He knows how I feel about wanting them together. But I REALLY don't like that I seem to be more comfortable with this girl than my friend is. A lot of the time he's quiet or just goofy or just talking without really saying much, and I've been telling him that he needs to be a bit more assertive if he wants this girl back. Or he just needs to cut all contact, which he's thought about, and agrees with, but doesn't want to do. I can tell by looking at him when we're all together that he's just thinking about wanting to be with her, but he doesn't know how to do it anymore. He's not giving her any challenge or really any reason to be with him.

This was mostly a vent, but if there are any suggestions about how to start coaching my friend to more steady happiness and self-reliance, that'd be cool too.