From experience and observation I have come to this conclusion: It is a bad idea to go to a guy with your relationship woe's, especially if you have any sort of history or the possibility of a future with him. And it goes both ways. I mean, what are we REALLY trying to achieve?
I have a male friend that just went through this very situation and he puts it like this: It is not just that we have already talked about these issues [granted, it was in dealing with ourselves] it is that I don't feel comfortable being "here" and I don't want to deal with her dating or interest in guys when we have already had to deal with the oddness of our own relationship.
And let’s be honest, too much of the time that oddness is something that is left unspoken, a rift in the relationship that you rarely address. You simply let the sexual tension build and allow this person to stand in as your “substitute” until a suitable mate comes along.
But I think maybe girls and guys are sending different messages when they try to communicate about their relational woes with someone they have been or are potentially interested in:
Girls are trying to say: look, guys are interested in me, I’ve been asked out four times in the last two weeks, that should tell you something, why aren’t YOU asking me out? Or, I trust you, that’s why I am telling you these things about my past relationships, ask me out so we can do things differently, I know you wouldn’t treat me like these other guys. But unfortunately guys read it as "I have these other guys, I don't need you. Don't be interested in me"
I don’t really know if I can speak to what I think guys are trying to get at when they talk to girls about their relational woes – perhaps you can all shed light on that for me. I have been confused one too many times when this has happened in my own life. I can only let you know that when a guy does this, a girl tends to interpret it as “I trust you and I want to let you in on this part of my life” – and we think that if we listens JUST long enough and gives the right advice or says the right thing – he’ll FINALLY realize he’s actually in love with US not the dumb girl he’s been discussing.