See Ya, Lindsay Lohan! Who Says All Men Prefer Younger Women?

Thanks to Desperate Housewives, suburban fortysomethings have replaced Britney and Lindsay as the sex symbols du jour. It’s about time.

Thanks to Desperate Housewives, suburban fortysomethings have replaced Britney and Lindsay as the sex symbols du jour. It’s about time. While the cultural wisdom may suggest that most men favor pop superstars just old enough to drink legally, some of us recognize that women over 40 can make better girlfriends and more sophisticated lovers than their more youthful, belly-ringed counterparts. Like the lawn boy on ABC’s campy hit series, I had my own brief foray into the paradise of older women, and I’m a better man for it.

Sign Up For Our Daily Newsletter

By clicking submit, you agree to our <a rel="noreferrer" href="">terms of service</a> and acknowledge we may use your information to send you emails, product samples, and promotions on this website and other properties. You can opt out anytime.

See all of our newsletters

A decade ago, I was a 25-year-old magazine staffer trying to navigate the seemingly glamorous world of Condé Nast Publications. Being set adrift in such an expansive sea of well-tailored talent should have provided a rich vein of dating potential for a straight single man. Yet I was stunningly unsuccessful in my efforts, fumbling about like some minor P.G. Wodehouse character reincarnated as a twentysomething publishing hack with Internet access and a gym membership.

My work-related inadequacies thus forced me to fend for my romantic life at book parties, gallery openings and any other velvet-roped events I managed to doubletalk my way into. At one such affair, I met a captivating redhead who, as an added bonus, was a media bigwig with much to offer in the way of career advice. Ruth was fit and fantastic-looking; to stand next to her, you never would’ve known that she was 49 years old-a fact that eluded me when we met. Looking back, her lengthy digressions about Studio 54 and Patti Hearst should have stopped me cold. But as so often happens when copious amounts of complimentary off-brand vodka are involved, the night fell into a passionate state of affairs, leaving me no time to check her paperwork.

I soon began to enjoy the fact that she was older. Ruth had a wealth of life experience, and she brought this wisdom into the relationship. She was nurturing, warm and too out of touch with popular culture to realize that my “conversations” were simply recycled episodes of Seinfeld. And she did not impose the artifice of commitment. There were no demands for daily phone calls, or inquiries as to what our future together might look like. Ruth was able to date just for the moment-not the norm with women my own age. This independence was liberating, and my commitment to her grew out of respect, not a request on her part.

But more than anything, Ruth fell squarely into the wheel house of the female “sexual prime.” Like a well-rehearsed orchestra, Ruth’s talents had blossomed with years of practice; she was playing with the sophistication of the Vienna Philharmonic. And, unlike younger women I had dated, Ruth had few inhibitions. I recall several public romps in various museums that were likely jailworthy under the iron hand of Giuliani’s “decency” laws.

And Ruth’s emotional openness stood in striking contrast to my youthful detachment. Her willingness to discuss her broken marriage and career failings taught me how to open up and communicate-not a skill I had in surplus at that aloof age. By leaving herself so exposed, she showed me the difference between vulnerability and insecurity.

In fact, things were going very well-until the night we accidentally bumped into Zoe, her stunning, midriff-baring 24-year-old daughter. Men face enough romantic challenges as it is; the desire to sleep with your girlfriend’s youngest child is an extra hurdle we don’t need. But with her blue eyes and bohemian-chic outlook, Zoe was exactly the sort of woman I imagined myself settling down with. And here I was, dating her mother. If I ever had a chance with Zoe, this reality reduced the odds substantially (as did the fact that she was happily involved with a well-known artist).

Ruth was concerned that her daughter might not approve of our affair, so we were forced to create an elaborate ruse: I became Ruth’s private yoga instructor, offering personal tutorials in exchange for media-world advice. That most Three’s Company plots are rooted in better logic seemed unimportant to Ruth as she explained all of this to Zoe over a late meal at the Corner Bistro. Our explanation, in fact, raised more questions than it answered. Why, for example, was her mother out with her “yoga instructor” past midnight on a Tuesday? Why was a man so devoted to clean living ingesting red meat and Scotch with the fervor of an underfed Teamster?

The difference in our age became glaring when we socialized with friends. I grew to resent spending every Friday night at stuffy dinner parties discussing the escalating cost of Ivy League tuitions-especially when my most pressing economic concerns involved securing funds for upcoming Pavement concerts. And while Ruth never said anything, I don’t think she felt comfortable with my gang, for whom “home décor” meant replacing our post-collegiate milk crates with equally unattractive unfinished wooden bookshelves. Making plans became an exercise in choosing between the gentrified bohemia of the East Village and an evening of canapés on Park Avenue. Neither of us fit neatly into the other’s real life, despite our efforts to fake it.

The clincher came during a brunch I rashly set up with my parents during one of their spur-of-the moment weekend visits. I had told them I was dating someone, but did not provide any significant details. My folks are intelligent people, but they came of age in an era when courtship was a simple, expedient enterprise. They have never been exposed to the limitless romantic potential-or neurotic overanalysis-that accompanies modern dating. I usually operate under a strict “don’t ask, don’t tell” policy.

Yet there I stood, one sunny Saturday morning, introducing them to my “chatty older ladyfriend,” as my mother would come to refer to her. While my father’s sidelong glances indicated a mild sense of confusion, Ruth and my mother hit it off, beginning a long discussion about the flea markets below 26th Street. And as fate would have it, they were both devotees of Murder, She Wrote. As they professed their mutual admiration of Angela Lansbury, a critical recognition dawned on me: Ruth and my mother were contemporaries. It suddenly felt as if I were dating my aunt, not a sultry divorcée with an account at La Perla.

As it turned out, Ruth was feeling the same way, which made the eventual breakup easier. Though I missed her for many months thereafter, it was time for me to get back to being turned down by women from my own generation. She is nearly 60 today, and probably a grandmother, which makes any sort of fallback far too weird for me to even consider. Not that I’d really want to. I’m now dating (at least until she reads this essay) a perfectly youthful 32-year-old, and she is the beneficiary of what I learned from Ruth: that older women are often self-aware and deeply sensual, but differences in age present some quirky, perhaps insurmountable obstacles. What’s perhaps more important, though, is that Ruth opened my eyes to the possibility of a partner who has both the limitless enthusiasm of youth and the level-headed steadiness of maturity. So here’s to you, Mrs. Robinson.

Peter Hyman’s first book, The Reluctant Metrosexual: Dispatches from an Almost Hip Life, was published in August by Villard.

See Ya, Lindsay Lohan! Who Says All Men Prefer Younger Women?