dubiousjacob wroteSecond, all of the bigger women I have dated have been very self-conscious about their weight. They weren't comfortable with themselves like a lot of you guys are. They always talk about losing weight and how bad they feel about themselves, and I don't know how to say much more than "I like you the way you are" without sounding like a perv. Several of them gained weight (not on purpose), and I told them they looked cuter but they didn't believe me

This right here. I've relived this scenario a few times myself. I have this uncanny ability to fall in love with women who gain weight and hate themselves for it. Of course, it's impossible to convince a woman that she looks beautiful if she refuses to believe it herself. Not to mention they can't understand why I feel the way I do.
The one who does believe it has to be out there somewhere, right?
And my family has always been a little puzzled by my taste in women, but ultimately they just want to see me be happy. Hopefully yours is the same way, even with the teasing.