Ever date someone considerably older than you? When I was twenty-one, I dated a thirty-eight year old woman who I went to school with. My family (mom) did not like that, but the relationship lasted nearly a year.

I don't think I ever "dated" anyone more than 5 years my junior/senior. Sex, yes. Dated, no.

When I was 19, I dated a 36 y/o for a few months. Sex with her was some of the best I ever had actually.

When I was 19-20, I was in a relationship with a 32 year old woman. On the flipside, my last girlfriend was eight years younger than me.

The oldest guy I've been in a relationship with was 7 yrs older than me. He used to joke that he was robbing the cradle with me because of that, but I don't think it made that much of an impact because I was 22 when we hooked up. So he was 29 and I was 22. The oldest guy I've had sex with was 13 yrs older than me but I was 25 at the time. I've always dealt with men older than me anyway but usually no more than about 5 yrs older.

The guy I'm dating now is five years older than me. The guy I lost my virginity to was four years older. For some reason I always gravitate to guys who're approx. five years older.

I dated someone 16 years older when I was 20. It was awful, and not due to age. He turned out to be an awful person.