Most Helpful Girl
I have to say, i've been in a similar (not the same) situation. I was the fat girl, constantly being rejected back and forth by guys I liked. They liked being around me and talking to me, just never wanted to date me or even worse, date me but in secret (yeah, shitty I know..).
I finally decided I was done being the fat girl and over 4 years lost 90 lbs. (Amazing how cutting back on eating and exercising works…) I have to say, a lot of these same guys who rejected me before and now asking me out left and right. My attitude at first was to reject anyone who rejected me… but losing the weight has def. given me a different perspective on life. I've given some a chance, but they have to work even harder for my attention. ;D
This guy… seems way insecure about what other people think. And that's not the guy you want. If it's not your weight he has image problems with now, his other insecurities will show. And may bring you down in other ways. This guy sounds like he has issues. If he really wants things to work, let him work for it! But I'm sure there are better options out there.