02/27/2014 06:22 pm ET Updated Feb 02, 2016

The Gay "Cougar": Why the Men I Date Keep Getting Younger

If we were to play the Sex and the City game with the guys on Looking, who would my counterpart character be?

That's easy: I'm so Dom. It's not that we have similar temperaments, because we don't. Not the way Miranda and I did. And it's not just about our closeness in age. (Dom turned 40 in the show's sixth episode; I'll be 45 in May.) It's more for the way we love and lust, which I suppose makes our connection more like the one I used to have with Samantha.

When Patrick invited Richie, his new boyfriend, to Dom's 40th-birthday celebration, qualifying his and Dom's early hook up with "I'm a little old for Dom at this point," I understood exactly where Dom is coming from. I've been living abroad since 2006 (in Buenos Aires, Melbourne, Bangkok and now Cape Town), and the men I date seem to get younger every year. Twenty-two is so much more scandalous now than it was when I began dating 22-year-old Leandro six months after moving from New York City to Buenos Aires.

He was my first boyfriend who wasn't born within five years before or after me. When we broke up several months later, I figured I'd return to my regularly scheduled age group, but most of the guys who came after him, both the serious romances and the casual flings (Matias, Marcelo, Alejandro and Gonzalo in Buenos Aires, Jayden in Australia, David in Bangkok), were in their twenties.

While I'd love to say it's my youthful glow that makes me popular in the kiddie dating pool (several years ago, a 19-year-old mistook me for 24, but I still blame that on the flattering lighting in the Auckland club where we met), the truth is that most of the age-appropriate men I meet would rather wade there, too. I recently went on several dates with someone who told me that he was initially wary of going out with me because he thought I might be too old for him. He was worried I'd be a tired old queen whose fun days were far behind me.

He was 51 years old!

That's 30 years older than Jayden was when he and I met four years ago in Melbourne on a night when he was out with his soon-to-be ex-girlfriend. That's how young he was: He hadn't yet come to terms with his sexuality, never mind coming out of the closet. As he later told me after ardently pursuing me, our meeting provided his moment of clarity. Meanwhile, I knew he was all wrong for me. He was still in university and dependent enough on his parents to be terrified to tell them that he was gay.

Despite the social and economic limitations of his youth, I was attracted to his openness and his fearlessness (if coming out wasn't the dare involved). I was his first boyfriend, and he dived right into the relationship, unencumbered by the baggage of past loves and disappointments. He wasn't jaded. He may have looked like a baby, but the courage and vigor with which he pursued me was all true man. As with most of my relationships with younger guys, none of which were just about sex or my paying their way, we had a smooth ride out of the starting gate because there weren't all those roadblocks that get bumpier as potential mates get older: fear of rejection, pride, a need to keep score lest the scales tip causing him to lose the upper hand. He hadn't lived long enough to compile a lengthy list of rules, so he forged recklessly ahead.

Sadly, that old devil called doubt, with insecurity as its pitchfork, would eventually come between Jayden and me. Several months into our romance, he told me about a dream he had in which I left him for someone closer to my own age, a grown-up with a career and a home who was out and proud. I may not have known what was best for me, but Jayden thought he did.

I knew the end was coming, though it didn't arrive for another six months. People from different generations can grow even farther apart. But if I learned anything while sorting through the wreckage of our relationship once it was over, it wasn't that guys half my age are too young for me. I couldn't imagine getting involved with anyone else who wasn't completely out of the closet, but I wasn't ruling out a future boyfriend who was born after the Class of '87 graduated from high school.

I don't believe a twentysomething is inherently worse for me than a man in his forties. I've dated enough of my contemporaries to know that they're not necessarily more mature or well adjusted. Stevie Wonder, Kate Bush and The Beatles created some of the most enduring music in the history of rock and roll well before they turned 25, so youth does not necessarily equal undeveloped. And being older certainly doesn't mean you have your shit together. It's not like I lived happily ever after with any of the people my own age whom I dated before I turned 37. It's not like any of those relationships were easier -- or better.

I hate that guys born after the Reagan Administration rarely have the same points of pop-culture reference (cases in point: Gonzalo's Transformers obsession and Jayden's preference for the Glee version of "Don't Stop Believin'" over Journey's 1981 original), but I'd rather commit to an enthusiastic twentysomething whose iPod is stocked with bad pop music than a middle-aged man whose romanticism is tempered by a long list of don'ts and who is terrified of losing control.

I didn't fall for Jayden because of his age, but loving him was like bathing in a fountain of youth. When he and I split, I didn't only lose the guy. I lost what he represented: youth and what part of me worried might be my last chance to recapture it. He was still young. His heart would go on because it had only half the wear and tear of mine. He had everything to look forward to. I had too much to reflect on.

I imagine this must be how a lot of guys my age feel, too haunted by the past to forge too bravely ahead into the darkness of the future. That's the cost of experience. I'll take the fear-free, the shining light of wild, youthful abandon, whether it comes in vintage packaging from before 1974, or wrapping that was made in the late '80s. That was the era that gave us Dangerous Liaisons, MTV's 120 Minutes, and "Oscar winner Cher." Who's to say it didn't produce Mr. Right, too?