To Show or Not To Show

I met a guy online at an off the wall kind of dating site. It's strange how these things happen, isn't it?

Anyway, he sent me pictures of himself. He's a bit older than I generally date (I try to stay within 10 years, and he's 15 years older than I am). But I figured that it wouldn't be too much of a stretch, especially if he was intelligent, successful, independent, and other attributes I value in a mate. Intelligence is a deal breaker, as is financial independence. Looks? I'd rather be with someone I can carry on a conversation with than someone whose looks could impress others. They just don't matter that much to me and never have.

Well, so he asked for pictures of me. What? My charm and sexy phone voice aren't enough? Right. But he still wants pictures, and is apparently unwilling to continue chatting with me on the phone without said pictures. So I wonder: Should it matter to me that it matters so much to him? Am I being naive in assuming that looks don't matter to other people like they don't matter to me? Am I just freaked out about my weight? Probably all of the above.

I've decided to go ahead and send him a picture. My assistant took it today. Frankly, I think I look pretty good. Yes, I'm overweight and out of shape, but that's changing. I'm down 22 pounds now, and I think that's pretty damn good. I even started going to the gym again. I spent over an hour and a half there last night, and I might even go tomorrow before work (assuming I get my sleepy butt out of bed).

I'm well aware of the fact that, if he's unwilling to even consider the possibility of friendship because I'm presently overweight, he's a loser and it's totally his loss. But it still stings. It must be what people with scars on their faces feel like. The difference? Those people can use cover-up. There's only so many ways to camouflage fat.

Anyway, wish me luck! Or him, that is.