[quote=Blogstar]Ex-girlfriend? I guess that makes the real question; How much baggage does Kev have to work through before he can be in a healthy relationship, and especially not attract and spend several years with women who are beneath him?[/quote]

As your pretend Internet dad I’d probably say work on kev first. I’d front the $ for appropriate therapy. Maybe some kind of encounter group? I feel this situation is partly your fault. Even if it isn’t it’s the right way to look at it.