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Dating An Older Guy…


If you’re gay and want the scoop on May-December relationships (and what makes them last), look no further.

By Stephen F. Milioti

aybe you met him at a dark bar and didn’t realize the age gap; perhaps you were aware of the difference and barely gave it a second thought…or maybe it’s the kind of relationship you swore you’d never have. But now you’re dating a guy much older than you — as in a dozen years or more. Once you’ve made the decision to date up in age, you’ll face some new issues if you want it to work. Here, how to have your best shot at lasting success.

Success Secret #1: You’ve got to be equals
What if your date seems a little too excited about all those years between you two? Case in point: David, a 27-year-old marketing manager in Stamford, CT, met a 50-ish guy at a party and agreed to a date. “I’m a mature guy, and I didn’t think too much of the age difference — I knew we’d have plenty to talk about,” says David. But without warning, that
“Research shows that inter-generational relationships tend to be quite successful.”
first date quickly went sour. “He kept telling me I was a ‘prize.’ It was flattering the first time, but by the fourth time he said it, it had gotten old.” And the objectification escalated: “When the check came, he grabbed it and said, ‘Please, you’re just a baby, I’ll get this.’ Clearly, the guy had an interest in being a sugar daddy, and that wasn’t what I wanted.”

Younger men can be just as guilty of exploiting the age gap. Larry, a 52-year-old creative director in Los Angeles, recently went out with a 29-year-old. “As soon as we sat down for dinner, he checked me out and said, ‘You look like you work out a lot,’” he remembers. “Then he added, ‘That’s a real turn-on for me — I love the muscle-dad type.’ Muscle dad? I was disgusted.”

If you sense your date’s more interested in your birth date than you, the relationship is starting off on the wrong foot. But don’t assume everyone your date’s age will have the same viewpoint — just keep looking for more open-minded men. “An intergenerational relationship can have the loyalty, trustworthiness and honesty of any strong relationship,” says Michael Koetting, a psychotherapist in private practice in New York who focuses on gay male issues. “Clinical research, including my own, shows that intergenerational relationships tend to be quite successful,” he says.

Success Secret #2: Embrace your differences
Koetting says there’s one key reason May-December pairings work: “A difference in age means there’s generally less competitiveness and jealousy.” For instance, two guys the same age might inadvertently compare who’s farther along in their career. An age
There are downsides, like when you find yourself playing the sugar daddy.
disparity can eliminate this type of jockeying. Overall, says Koetting, age is a minor concern. “The qualities of these people bring them together, not their ages,” he says.

Another necessary component is having realistic expectations of one another. “There are things I realize my boyfriend can’t know, understand, or relate to because he doesn't yet have the life experiences,” says Greg, a 39-year-old operations/planning manager who lives in Dallas and has been dating a 22-year-old for almost a year. “It's a process that has its own timetable. On the other hand, he realizes there are some things I don't care to experience again, like staying out until 4 a.m. at a dance club. Well, maybe once in a while.”

Success Secret #3: Talk about your concerns
After sounding out his boyfriend before getting involved, Greg is dealing just fine with the age difference. “For the record, he approached me!” he says. “I was a bit skeptical in the beginning, but the more I talked to him, I realized it wasn't a phase or something he just wanted to try.”

Greg admits there are downsides, like when he finds himself playing the sugar daddy — not out of desire, but out of practicality. “Probably the biggest challenge for us is that he’s just getting started professionally, while I'm well established in my career, so there's disparity in our incomes,” he says. But they’ve accepted it and dealt: “Recently, we took a trip where I had to cover the majority of the expenses or he couldn’t have come, and of course I wanted him along. He expressed concern that he wasn’t contributing, but eventually realized the reality of the economics and was able to enjoy himself.” Clearly Greg and his partner rely on good old-fashioned talking. “Communication’s a must. If something’s bothering us, we have to speak up — no keeping emotions in the pressure cooker.” And that’s sound advice for any couple.


Stephen F. Milioti is a freelance writer and editor who contributes to New York and Salon.
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