Nearly 60 and Loving It

Q: I am a woman nearly 60-years old and quite well off. I have become attracted to a man in his early 20s. In fact, he's finishing college this spring. He's bright and intelligent and young, and he makes me feel young again. He escorts me to opera, ballet and art gallery openings, but truth be told I'd want to be with him for the sex alone. It's better than anything I've ever known—intense, emotional and frequent. He's taught me about anal sex (which I've never been brave enough to try) and things like pocket rockets and ben wa balls. Sex with him is like a whole, forbiiden world I've loved exploring. The problem is my friends, family and his friends and family. On his side, everyone thinks he's doing something awful spending his time with an old woman. On my side, everyone thinks he's after my money and just wants to live off me. They are making life difficult for us. I'm in this for the ride and have no illusions that he loves me. I give him gifts because I like to and I can. Is there anything wrong with that?

Anne: It could be said that you are leading him down a bad path, encouraging him to rely on a woman for his livelihood. However, if both of you accept the rules of the game you've started, I don't see anything wrong with what you're doing. I would advise you not to sign anything.

Dee: Good golly. You're almost 60 and you snapped up a young 20 something guy?? How the hell did you do that? Conversation, escort duties and all the fucking you can handle (or maybe more, dare I hope?). Life has treated you well woman! Tell those screwball friends and family that they're just jealous and if they can't get with the program, to buzz off. Take life by the horns! You can't make your friends happy and they shouldn't have the power to fuck up your happiness.

A Horse Ain't Always a Horse

Q: My boyfriend of three months and I just finished watching Secretariat. I thought it was a sweet, brave and inspiring movie. Jim made wisecracks all through it until I didn't even want to sit there with him. When it was over I showed him the door and he acts like he doesn't know why I'm upset. This has pointed out that his attitude about the movie is present in all kinds of things—things I'd been willing to overlook. Now I wonder if I should be overlooking them. If his actions during a movie bother me this much, won't other things—more important things—bother me even more in the future?

Anne: I would say that this might be a sign of things to come, so maybe you should think through this relationship carefully. Life ain't a movie.

Dee: Know what I got out of Secretariat? He sired 600 foals! That was one fucking good horse. Really, are you asking us about whether you should stay with your boyfriend because he made fun of a "sweet, brave, inspiring" movie? Are you listening to yourself??

Harrison High School Jerk

Q: A guy I had a huge crush on in high school took me out once our senior year. We didn't have sex (though we came close) and he never called or really talked to me again. I always thought it was because I didn't let him "go all the way," but maybe it was because I was kind of chubby and wore glasses and stuff. I saw him a few weeks ago and I'm quite different looking. He didn't remember my name—or that we dated that one time—but he sure is interested now. What should I do?

Anne: Well, that stinks, but really, high school is over and done with. It all depends on how you feel now, as an adult. If you met up with him and find you want to go out, do it. I would say though, that if you have any kind of idea of revenge for the wrong he did you in high school, forget it. If he's still the same jerk he was back then, just don't go out with him again.

Dee: What can we say? Guys are jerks often enough when they're grown up. In high school there's no hope at all. They're totally hormone driven, with fucking on the mind morning, noon and night. If you didn't give it up, he might well have been stupid enough to forget about you. If he pulls the same shit now, blow him off—and I don't mean in the fun way you both will enjoy. Good luck.