Dating in your 40s. Ain't it a bitch? If you're not sure why it's a bitch, let me count the ways. First of all, dating just generally kind of sucks. For every one halfway decent person you meet, you meet 10 weirdos, flakes, sex maniacs, or just plain old people you don't gel with. But in your 40s, it gets much, much worse. For one, men in their 40s suddenly decide you are too old for them. Yes, you go your whole life dating men who are your age, give or take a year or two, and suddenly, boom! The only guys who want you are in their 50s or 60s -- or 20s. I suppose it has something to do with those barely-working ovaries. Or maybe it's Hollywood. Thanks to men like George Clooney, Bruce Willis, and Nic Cage, men have become accustomed to seeing guys in their 50s banging chicks in their early 30s. They just naturally think this applies to them too.