It was, by and large, one of the most engaging conversations I’d had with a man in the city in months. Tucked into a corner of a bustling café, speaking intently over wine and aperitifs on the subject of art (his impressive art, specifically) and language (he was French and his English was rough, but we somehow stumbled through a lively conversation) my attention was piqued. And he was handsome—thick head of hair, a strong stature, and a sly smile. But it was really a profound and rare sense of confidence that he exuded that was enthralling—the kind that comes only with age and experience. I didn’t want to pry, but he was older. Much older. He had been friends with Andy Warhol and went to art school with Paco Rabanne. He had retrospective exhibitions of his work. You do the math: He was no millennial. But as his friends relayed to me that evening, women still fell at his feet. I felt somewhat vindicated, and when we began an innocent email exchange soon thereafter, I flirted with the idea of a May-December romance. After all, he was refreshingly honest and worldly—qualities that eluded the modern-day guys closer to my own age. Moreover, he had an overwhelming ability to be subtle about his accomplishments, as if he had lived long enough with them that the idea of boasting seemed pointless; they simply spoke for themselves.
It was all very attractive and when I told a colleague of the elder statesman, she regaled me with a story of her own. Dating a graying and distinguished journalist for six months, she was enthralled by his throwback moves—they seemed uncanny in today’s dating market. “There was something very reassuring about the old-school chivalry,” she explained. “He was really graceful about being a gentleman, making little thoughtful actions like opening doors and relieving bags from my shoulders. Performed without a hitch and without exception, they seemed like second nature. It’s also romantic not to have to wait around for a text back. I admire a generation that knows how to make a plan for dinner and stick to it.” And what jaded modern dater wouldn’t? But I, of course, couldn’t ignore the looks of concern my other friends shot me when I revealed the silver fox’s age.
To be sure: No matter how progressive one thinks they are, when older men take up with younger women, talk of daddy complexes, gold-digging, and trophy girlfriend statuses are most likely to abound. Certainly couples make it work—newlyweds Mary-Kate Olsen and Olivier Sarkozy come to mind—but there always seems to be a tinge of illicitness when it comes to an age gap. It’s an unfair judgment, especially when you consider true chemistry often crosses all sorts of divides—race, class, gender, and yes, generational. Now admittedly, I stopped emailing the artist soon after meeting someone else—true, someone closer to me in age—but I was at least expanding my idea of dating and what my future beau may look like. So this date night, don’t simply write off a man of a certain age because of a few gray hairs. While your new beau makes you dinner (because he actually knows how to!), slip on your Self-Portrait tiered lace midi dress while you follow him around his well-stocked kitchen. Attend his art opening in Faith Connexion’s off-the-shoulder black crepe dress and dazzle him with your style and art acumen. And when you bring him to meet your progressive group of friends, try timeless denim on denim with A.P.C.’s chambray henley and matching Gucci garden jeans.
