Does he really think I'm too good for him?

[lotus-blossom-08]

This guy friend of mine and I have been dating for about six months. Sometimes when we are really intimate (like, we're cuddling and just laying there in each other's arms *le sigh*) he will say things like "there are a million guys out there just like me" or "I'm nothing special" or "you could do so much better" and when I ask him about it he says that he just doesn't want me to rule out other guys I could be dating (even though he hasn't been seeing other people either since we've started going out).

I've known him for a while and I know he has self esteem issues when it comes to girls. I'm not sure if he's saying these things as a variation of the "it's not you, it's me" line or if he really thinks that he's not good enough for me. If he does think that he isn't good enough for me, is there any way I can give him a much needed confidence boost and let him know that he means more to me than some random guy out of a hundred others (and I have told him this, many many times).

[Chuck-]

He either feels really insecure as you say about himself. Or he is very underhanded at digging for compliments. I've been with girls that I personally thought were out of my league, but I didn't want them to think that so I would never mention it. It also made me strive to be the best guy I could be. So I believe insecurity should be followed with progressive action, if he thinks that he isn't good enough for you, he should be trying to make himself good enough for you in his own eyes.

I'll step off my soapbox now.

I don't really know how you could make him feel special. If other people told him how lucky you are to have him that might work. He might be hearing from friends how lucky he is to have you which might make him feel undeserving. It's a tough situation and I don't envy you.