Dating Older Women
Just when you thought you couldn’t hear any more about Demi and Ashton’s breathless, "she could be his mom" romance, along came Desperate Housewives, featuring Eva Longoria, her jailbait gardener, and their sweaty primetime frolic. And what have we got down the road? Next summer’s sequel to the ultimate woman/boy classic, The Graduate. A trend? Maybe — at least in Hollywood. But how do real men feel about older versus younger women? To find out, we assembled five guys, 25 to 50, who’ve dated, married, and dallied up and down the age range — and are willing to talk about it. We wined and dined them (emphasis on wined) until we got them to tell all.
- David Amsden, 25, novelist, has always dated older women and confesses he’s "never even kissed" a woman younger than he is.
- Steve Friedman, 49, writer, never married, has dated women from 17 years younger to six years older. He’s still looking for a woman to have a family with.
- Geoff Loftus, 50, communications executive, had a fling with a 37-year-old married woman at 17. Divorced in his 30s (when he dated both younger and older women), he is happily remarried to a woman his age.
- Joel Warren, 44, co-owner of New York’s Warren Tricomi hair salon, divorced after 12 years of marriage and currently lives with his 25-year-old girlfriend.
- Jamie Savian, 36, anthropology professor and cabinetmaker, had a serious relationship with a single mother eight years his senior, but recently married a woman his age.
Dan Jones for MORE: You see two women on the street — one 45 and the other 25 — and you’re equally attracted to both. What do you see in the older woman that’s different from the younger one?
Jamie: I doubt I’d find the 25-year-old as attractive as the 45-year-old. I’ve always thought that women who are starting to show their age are the most attractive — lines on the face, a leanness of features as opposed to the doughiness of youth, and a confident way of carrying herself.
Geoff: I’m with Jamie. I’d go for the 45-year-old. And I probably would have gone for her when I was 25. The older woman has character in her face — she’s lived life. The 25-year-old has a kind of unformed prettiness. She hasn’t "become" yet.
David: What attracts men to women is vulnerability — and an older woman has all the vulnerabilities that come with age. Or maybe she’s divorced, which I’ve always found oddly attractive. But, you know, Lindsay Lohan was just on the cover of GQ magazine, which is for men in the 30s, 40s, even 60s. And she’s, what, 18? So I guess I’m wondering if we’re being honest about this.
Steve: I know a lot of men who wouldn’t buy that you’d be equally attracted to both. But for me — someone who wants to have a family — I just don’t have a shared reference with the 25-year-old. On the other hand, the 45-year-old probably isn’t going to have kids, so it’s kind of a cruel calculus.
MORE: Which brings up an important issue. Say you’re casually dating someone older. Is there a threshold you cross, when the relationship becomes more serious, where the age difference becomes a problem?
Geoff: For a woman in her 40s who still wants children — if she hooks up with somebody it can quickly turn into her saying, "Let’s start screwing around without birth control before the wedding!" That puts a lot of pressure on a relationship.
Jamie: When I was 30, I was in a serious relationship with a 38-year-old who already had a kid. And as much as I’d like to think that love ruled the day, I know that the logistics of dealing with the kid were really tough. Even down to the mundane level of us driving together — I own a pickup truck and it has a bench seat, and the kid always had to be sitting between us. Little things like that become a real problem.
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]
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!"