What Men Really Think

About fake breasts, biological clocks, your money, and their new status as arm candy for older women.

By Daniel Jones

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.

The Guys

  • 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.

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