Sounds like he's depressed and has low self-confidence. I've been there, it sucked. Having a girlfriend will be a big help though. When you're in that state you only see yourself in a negative light. Your eyes only see what justifies that view. So much so you come to believe it. He probably was convinced he wasn't attractive to women and now you've turned his world upside down and he can't bring himself to believe it. He'll probably resist believing it for a while too so avoid getting into an argument if he doesn't believe your reasoning. Yet your encouragement makes him feel warm and alive inside and he loves it. It's kind of like when girls ask you "does this make me look fat?"
This might be one of those times where it's best not to say anything at all but just put your arms around him and embrace him. Show it rather than say it, you know?
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Silly question to ask, since we don't 'choose' do we? Don't things just happen? It's like asking the meaning of life.
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The guy just wants to be assured that your into him. Maybe he has never had as much luck with women in the past as he is now. So now those past relationships are growing self-doubt in his mind. Basically, he is just insecure at the moment.
Sounds like something an insecure person needs to ask, to gain reassurance from the person they are with.
straight forward question. He is probably just wondering what qualities did you choose him for.
Insecure? inexperienced? Captivated? Madly in love? Pick any, or all four. ; - )
He wants to know what you see in him long term short term, maybe want you to stroke his ego..
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