A lot of us, especially those of us with this personality trait that can, I admit, be maddening, care what girls think. No, we really care what girls think. To the point where if the girl we’re head over heels in love with says ‘no’ when we ask her out (okay, this collective editorial we is getting irritating), we think it’s because we have some big, huge personality defect.
[sub]Okay, 'nuff of that ‘we’ crap.[/sub]
And guys of that sort have ridiculously bad timing - especially in high school - so the feeling/image of worthlessness is allowed to perpetuate itself and grow stronger. Eventually, this feeling, and the self pity that accompanies it becomes too thick to see through regardless of what you (“you’re my friend, you have to say that”) have to say about it.
Sadly enough, sometimes it seems as if only The Perfect Girl can get through guys who are like that (after all, everything TPG says is the gospel truth), though a lot of us get over ourselves and look at things rationally. One way or another it’s just a phase. An indeterminately long one, perhaps, but it’s not irreversible.
So even if you’re not his Perfect Girl, help him see his own self worth (it’s possible) and he’ll thank you for years to come. He may even buy you dinner.