My first question to you would be… why do you want to meet up with a guy who says he’s messed up, is shy around women and wants to be alone? Is that really what you want?
It sounds like you may be putting yourself into a really difficult position where you’re going to have a lot of problems communicating and being in a real relationship.
Men aren’t fixer uppers. And if you get into a relationship with a man who is messed up and tells you that he’s messed up, he’s going to have no incentive to fix himself (which is the only REAL way a man is going to get fixed).
The other problem that you have is that he isn’t “stepping up to the plate”… he’s not making that next move.
This is a problem because if he’s doing that now, he’s going to do that later. It’s possible that if he’s a shy musician, he just doesn’t know what he should be doing. But is that really what you want? A man who is clueless.
My first suggestion would be to rethink getting together with this guy. Just from what you said, he doesn’t sound like he’d make a good partner. I could be wrong. But that’s the impression that I get from this guy.
If you really want to move forward with him and he’s not getting the hint… you need to do something a little bit less subtle. Ask him to invite you out somewhere.
Notice that I didn’t say to ask him out… I didn’t say to plan a date… I didn’t say to tell him where you want to go. I said to ask him to invite you out somewhere.
Basically, if he isn’t making the next move, you need to let him know that this is what you want, in no uncertain terms. If you ask him to take you out and he still doesn’t, I suggest you move on and find someone who is a little more mature and doesn’t need you to hold his hand in order to be a man.
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