Jamie: But seriously, in spite of all the things women may have accomplished, there is some quality in them — and I’m not sure whether it’s financial or emotional — that they do want to be taken care of. Recently, my wife’s work arrangement changed in a stressful way. She was upset about it, and I tried to comfort her by saying everything would be all right. But that’s not what she wanted to hear. What upset her was the realization that she’d always have to work, because I wasn’t a traditional man who would ever make enough money to support us both. I’ve always seen her as a career woman, so it didn’t occur to me that she would need me in this way.
Steve: In my experience, women in their 40s who are making tons of money — a lot more than me — are usually much more vocal about expecting to be paid for. And women in their early 30s and late 20s are much more like, "Oh, let me get this." That’s one of the reasons I like younger women. Money isn’t the central metaphor for them.
David: I’ve gone out with women twice my age, and I’ve never confronted that — maybe because I’m so young. In my experience the woman has always been happy that I’m not the one taking her out.
Joel: Today you have all these women, like Demi Moore, who are rich and have their arm-candy boyfriends, and they are also financially able to keep themselves up, to keep themselves attractive to that person.
Jamie: They’re in the position that men have generally been in. So now they’re wrestling with that whole idea of how can that power be used? Should it be used to find a young man? Should it be used to find a soul mate?
Go After What You Want
MORE: Or maybe it should be used in the same way men have used it, to be sexually aggressive, to know exactly what you want and to go after it.
David: I think for women there is still some reticence about being that dominant — to say, "This is what I want. These are three things that will make sex better for me."
Joel: If you ask me, by the time you’re 45, you should have figured out what turns a man on and turns him off.
Jamie: That’s right. Everybody’s had sex at that point. Everybody’s done it enough to know what works and what doesn’t. Whereas younger people are all worried about performance.
MORE: Are women over 40 better in bed?
David: A friend of mine who’s 32 says that sleeping with young women is like putting together a stationary bicycle in terms of how much work you have to do for the payoff. You’re moving around these parts and struggling; whereas my experience has been that women who are a little older…It’s incredible how much better the experience is than with women my age, where it’s this postadolescent, collegiate, "What the hell are we doing?" kind of thing.
Steve: But if you’re sleeping with someone much younger who has been mostly with guys her age, she’ll probably be happy you’re more relaxed and know something about what you’re doing. It’s similar to when I was younger and had relationships with older women — it’s like, "Oh, here’s a woman who is confident and knows things."
MORE: When you’re with a woman who’s much older or younger, do you feel influenced by the opinions of friends, family, strangers?
Steve: When I’ve dated women significantly younger, I’ve been very aware of what people are thinking. My women friends, especially, are like, "Who does he think he is?" But with my family, it’s just, "Please, God, let him marry her." She could be 15; she could be 55. On the other hand, if I’m with an older woman, my female friends all think, "He’s seen the light! He’s finally grown up!"