The situation sounds like a college friend of mine who "somehow" always "had the bad luck" to fall in love with g
ay men. Time after time after time. It didn't take me long to realize that a guy's attractiveness was inversely proportional to his availability. Being attracted to the unobtainable takes away all responsibility for one's own love life and happiness or for any need for self-improvement.
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My personal g.a.ydar is completely busted half the time, always when I find the guy interesting, I even had a crush on someone who hadn't come out to himself yet (so I now joke that I 'break' men and turn them g.a.y) - but in the same time I can rationalize why I am attracted to certain guys that I know would not be a good idea to date.
I was keeping myself from being happy with someone because I didn't have the self confidence to think "hey! I deserve to be happy, bring me the cute* guy for once".
I found someone who boosted my confidence and I know I act and look "better" and happier and I'm probably more attractive to other guys.
What I wanted to say is, I didn't need therapy to come to this conclusion, because I did the work on myself to try an analyze what was going on, but OP's friend could use it, I just don't know if there's a good way to broach the subject...
* I have a very large spectrum of what cute means, and it's not just the looks - I'm not looking for a supermodel since I know I'm not one, and I believe look is not all there is in someone.