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In fact, Stephanie was even more beautiful than her older sister, and I just had to pursue.

For one semester, Stephanie and I had a frolicking good time.

.” No matter what I said, or what nice things I did for Karen, she was out of my league since I was younger.

Karen was a 17 year old junior, and I was an incredibly good looking and intelligent 16 year old. This is exactly what my mom told me every time I brought her cupcakes.

Stephanie was Karen’s younger sister and she was hot!), there are thousands of other instances of cross-generational relationships that die a quick, painless death. Because he was born in the 80’s, right about the time that you were losing your virginity in college. This is a valid concern to men looking to have families, so let’s not overlook it. It just seems far more likely that a) he’s bragging to his friends that he might get to sleep with a woman 20 years older than himself, or b) you guys really might be compatible if only he were significantly older or you were significantly younger. A caveat which I must acknowledge: if neither of you desires children, then you have a far better chance.Because he’s been in the workforce for oh, about four years. But still, I’m a big proponent of life experience and wisdom. So even if this young man’s interest in you is completely pure, even if he wants to have a real relationship with you, you guys are most likely doomed. But presuming he does, if I were you, Carla, I’d probably have some fun. Maybe not all of them, and maybe not this particular guy, but most guys in their 20s think an older woman is easier and hornier than women their own age.Time creates wisdom – but it also creates responsibilities and complications – mortgage, kids, career, etc.All of this makes dating more and more complex as we get older. Still, most of them fail miserably, for the exact same reasons that I think Penelope is suggesting.

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You don’t want to hear it, but, there are same basic rules of dating as a women, post thirty-five, that are worth following … Which isn’t necessarily a bad thing (give me Angelina Jolie over Emma Watson any day) but it does mean you need to be realistic about the kind of men you’re going for.

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