Steve: What I worry about is looking into a future with a woman who’s significantly younger than me, because I see myself in a wheelchair and her pushing me around. Whenever I see couples like this — where he’s older and she’s the younger, more vital one — it makes me uncomfortable.
Joel: And that’s what I strive for! [laughs] But seriously, also a problem with younger women is you don’t know if they’re always on the lookout for a bigger, better deal. Older women may be more honest about their intentions, because they’ve been through life and they’re better at knowing what they want and explaining it.
Dating Younger Women
MORE: But going back to what David said about Lindsay Lohan — there are a lot of media images of younger women out there, and a lot of men who date younger women simply because they can. What does a woman have to do to keep a man’s attention as she ages? Is Botox the answer? Plastic surgery?
Jamie: I actually don’t like fake breasts. Am I wrong in that?
Joel: I like fake breasts. They’re better than real ones. I mean, breasts are visual things, and it makes women feel better when they look better.
David: It’s a fine line, and I know I’m very knee-jerk anti-plastic surgery. But then I think, I’m not knee-jerk anti-dyeing your hair. So what’s the difference between dyeing your hair and plastic surgery?
Geoff: I don’t think you have to cut any flesh to dye hair.
Joel: The thing is, when a woman is young and attractive and she walks into a room, she gets attention. And as a woman ages, she wishes she could stay in that moment. But it’s a mistake. Women should try to make themselves look their best for their age. At my salon, when women bring in pictures and say, "I want to look like that," it’s almost always a picture of someone much younger. And I’ll say, "Can you bring in a picture of someone your age who you think is attractive?"
David: It’s almost like our culture has forgotten how to make a 45-year-old woman look like a beautiful 45-year-old woman. The social machinery is to try to force her into the mold of a 28-year-old.
Geoff: There’s a tragic look to women who struggle to stay younger-looking. In many cases they’d be more beautiful if they just let it go.
Steve: If you ask me, women worry too much about how we feel about their looks. Women always say, "Men say they don’t want women to wear makeup. But the truth is you like us better when we wear makeup." But the truth is, I really don’t.
Geoff: Men do tend to be obsessed with appearance, though when I was 25, I was a lot more obsessed with it than I am now. My idea of what’s attractive in a woman has changed a lot. Now the hair doesn’t have to be perfect, or the weight, or the face. I used to want to date only nines and tens. And as I’ve gotten older I’ve realized how ridiculous that is.
MORE: What about the "confidence factor" of older women? Can that make up for some of the potentially less-sexy aspects of physical aging?
David: One thing I’ve noticed with my mother, who’s in her early 50s, is that a lot of men of her generation don’t know how to deal with a woman who doesn’t need to be taken care of — who can afford a Lexus, who owns a house, who owns her own beach house. Whereas men of my generation know exactly how to deal with women like her. Have fun! We never want to have to take care of anyone but ourselves.
Geoff: Which is why 50-year-old women don’t want to date you. [laughs]