I've never been with someone older than me. The oldest was just 4 days younger than me.
It seems to be I've dated/hooked up with more older than younger women. It seems they're also more attracted to me than younger women I guess. I find younger women more superficial about looks and tend to flock in droves to the guys over 6', flat abs, spiked blonde hair/popped collar types.
In the words of Bill Clinton, "I feel your pain". Most girls my age only seem to care about 3 things:
1) If you are "hot"... like fashion catalog hot
2) If you played sports in high school... never mind that that was 5 years ago.
3) If you look like you have the potential to make a lot of money.
Doesn't matter what kinda guy you are. You could be the greatest guy in the world, and if you don't have at least two of those three things, then girls don't care... try to convince them that you aren't worthless and they will start to assigning negative traits to you.
I totally agree with you. Guys want nice girls, and girls want guys who are jerks. I've had many arguments with a female friend over this, but I'm the only one who can back up my position with examples, and she's basically admitted I'm right.