‘I have a problem that many would not, on the surface, see as a problem: I’m getting hit on by men in their early twenties—a lot.’
I’m riding my Segway home from a movie at 11 pm on a Monday night. I stop at the light on Broadway and Prince Street, and a handsome young man walks up to me and says, “Do you realize how cool you are? I’ve always wanted to ride one of those.”
“Hop on,” I respond, and he does.
After a spin around Soho, I drop him back at the subway, and we exchange cell numbers. By the next evening, I’m meeting him in Union Square for a date. We’re on the Segway again, as I talk about my recent 60th birthday celebrations, I ask him how old he is.
“21.”
I almost crash. This is the first time I’ve been on a date with a man who could be my grandson.
I have a problem that many would not, on the surface, see as a problem: I’m getting hit on by men in their early twenties—a lot.
He reminded me of myself when I was younger. I, too, enjoyed the company of older men; my contemporaries often bored me. He seemed to be an old soul, but by our fifth date, the kid with father/authority issues took over, and it wasn’t all fun. We slowed down, changed course and worked it out. We remain in touch—at a distance.
♦◊♦
Recently, it was a 25-year-old I met on Grindr. Then there’s this 24-year-old who’s returning from Turkey next week. I usually think they’re older. The Turk has a full beard and is very much an “I’m in charge” kind of guy. That appeals to me. In most of my life, I’m the man in front of the room, the leader, so in romance, I like to relax. However, I can’t cede power to a clueless kid. So, what am I getting myself into?
I understand the seduction of it: the charm, the brightness, the excitement of skin that still fits. The parent in me, the avuncular mentor, is also activated. It’s not just physical. It feels good to be appreciated for my life experience while also being seen as hot.
Being a Hot Daddy brings all kinds of warning labels and limitations. Is this a subtle (or not so subtle) form of self-sabotage? A new version of pursuing the unavailable man? Getting involved with a man 10 or 20 years younger doesn’t phase me. Thirty-plus years younger feels like too much.
Therefore, I make sure to also date men closer to my own age. I had a date with a 69-year-old recently, and he was truly hot. (Unfortunately, he lives in California’s Napa Valley.) I’m eager to be non-ageist here and take each man on a one-to-one basis. I counsel clients to not live in policies, to be in the present and examine the actual situation, to look at the individual in front of them and ask, “What’s the best relationship I can have with this person?” I wonder, however, if some policies simplify and facilitate rather than merely limit. The statement “I don’t date men under 40!” sounds rigid but also oddly liberating. I’ve made a date for this weekend with a 45-year-old. I have a date for next week with the young Turk upon his return. For the moment, I’m holding the contradictions. We’ll see where it leads me. I’m playing a very broad field at 60 and proceeding with caution.
—Photo dicktay2000/Flickr



























I identify with your situation, as I usually prefer dating younger men myself. When I was younger, up until my early 30′s, I dated men my own age, and the constant problem was the degree of competition between us– all players in the same career and social scene. Finding trust was difficult. Then I had my first long relationship, 14 years long, and I was 8 years older. This was the first person I found who was as ready as I was for a deep relationship. After that, the age difference in my relationships got greater; I had gotten older but still liked men in their 20′s and 30′s. Now that I’m also 60, I’m like you, playing a broad field. But I have to say that I encounter as much inappropriate, immature behavior/expectations from older men as from younger men. For me, age is less the issue than maturity. Some of the 20-somethings I’ve known have been way more mature than some of the eligible 50-somethings I’ve met recently. There are a lot of stereotypes for 20-somethings, but what about some of the problems with 50-somethings, who, in my experience, have been overly aggressive about what they want, as in NOW, and with more of a one-track mind about sex, not to mention settled in their habits and inflexible. The MAIN thing I require is space, freedom, independence to do the range of things I love to do and pursue, and it takes another independent person to understand this and grant it in a relationship. Finding such a person at any age is not easy, but I think I am as likely to find it in a 20-something, 30-something, 40-something as in a 50-or-60-something. One of the most exciting men I met last year was in his 70′s, but I still haven’t had the openness myself to reverse my usual role and be the younger man in the relationship.
A very good point. Just as I was beginning to say for sure: No Men under 40, I am reminded that it’s always about individuals!
Humbled —> I thought I was cool for being a cougar getting 20-somethings’ attention.
Though, I did date a guy 30 years older than me. We almost got married. Realized it wasn’t what I really wanted and that it would bring a lot of trouble later and backed out.
Clearly you haven’t been using the algorhythm from the other article here.
Good point: YES they do come with WARNING LABELS! lol
I want to be you when I grow up (I’m 22).
I call bullshit. Segueways are illegal in New York City.
Yes Segways are illegal in NYC, And , I ride mine daily…
I teach college, so I spend my days interacting with a lot of 20-ish guys. They can be very appealing in countless ways and some of them do get Crushes On Teacher, but I also grade their essays, read their journals, and listen to what they say in class discussions – and there’s no way I could enjoy dating a guy at that still-unformed stage of his life. They’re just starting to figure out who they are and, more important, who they want to be, and they have so much learning to do; I don’t want to play the Pygmalion game in a relationship. When they visit 10 or 15 years later for Homecoming, THAT’s when they’re amazing – though they’re always partnered by then!
I think most older gay men have never worked in an elder financial abuse program. I did. For 8 years. In one of the gayest cities of the USA. May-December relationships are rarely, if ever authentic. The older man is only fooling himself, if he thinks that his financial situation will not be exploited. Just ask yourself: “Who is paying for everything or even MOST things?” I can site hundreds of “authentic” older/younger relationships that involved total exploitation of the elder finances. Why not? Some of you might say. Well for one thing it leaves an older gay man completely ALONE when all the money is gone. There is no money to pay for care etc when they need it. I look at these relationships, and see few, if any, where the younger man is the MAIN source of financial support. Few are egalitarian. There are a multitude of other problems as well, usually starting with a younger man desiring “another relationship” outside of the one they are in with the old man. There are also many relationships that are initiated by men finding younger men in a country outside of the USA. The younger man sees the older man as a “ticket” into the USA and once here, “escapes” to a more exciting life. Gay culture is layered with ageism and contempt of growing older. I think many older men are only fooling themselves when a younger guy looks at them over dinner and says “you are so hot” while YOU PICK UP THE TAB!
Stephen, I can imagine that is sometimes the case but it hasn’t been my experience. I do not have a large income and my much younger last two boyfriends both had good jobs, held their own and were quite proud of their financial independence. One of them now has his own business that is very successful and the other is well on his way towards that, with a job that pays better already than my own.
The first one taught me that open relationships are desirable, and I introduced that idea successfully to the second one. After seven years, we broke up because we realized we were more interested in being best friends and wanted to find sex and romance elsewhere. The break-up has worked well for both of us and we’re still very close and can depend on each other. No regrets. He’s with another great partner (his age) and I am not (and am enjoying my independence, temporarily!) So, I think it’s back to individuals. It IS possible to have a great older/younger relationship. I learned a lot from my younger boyfriends and treasure the experiences.
I’m a 46 year old gay man and, thanks to good genes passed down by my mother, I generally pass for 34-35 (37 on a bad day). I’m reasonably good looking and stay as fit as I can, and I lead an active social life. My closest friends are in their early 30s and I don’t feel older than them nor do they treat me like the senior in the group, mainly because they keep forgetting I’m 46, and because I’m still more active than half of them. I’m generally a stable kind of guy, but I like my occasional wild night and can still party with the best of them when I feel like it, which isn’t often. I rarely hide my age because I see no point.
However, here is my dilemma: I’m confused as to where I fit on the “potential date” ladder. Guys who look for men in their 40s don’t feel that I fit their 40′s “ideal” because I look much younger. And younger guys tend to back off once they learn I’m 46. Occasionally I click with someone mature enough not to care, or who likes me the way I am.. but they’re becoming increasingly rare. It’s getting frustrating, and I don’t know what to do. Help!
I have to say, after reading this one thing comes to mind. If you are on Grinder, you have to own your part, and if you are flirting with 20 year old guys I would think by the time you are 60 you would realize that flirting is a two way street. In other words, I would hope that the author understands that it isn’t out of the blue that this is happening, he may be 60, but his mind is acting like a twenty year old.
I am 60 and my partner of ten years is 39. We don’t know what the future holds but do know we are crazy about each other and tomorrow will work itself out. Unfortunately, most gay men that don’t really know us think and judge us like Stephen. Our straight friends are much more accepting. What a shame that gay men can be so shallow.
Faze.
Great age-gap discussion.
Imagine the tuttingtutting from het women feminists if this had been an older man and a younger woman.
As i often tell het men, they can silence feminists by pointing out that the sexual and romance behaviours that feminsts attack as being abnormalities in het men are found in equal measure in the lesbian and gay man communities. That broadly the behaviours of het men are like that of gay men and gay women.
That as a group it is het women, not het men, that is the odd man out
Interesting article about the age-gap phenomenon. I am in my mid 30′s, but I do like men a bit older because some of them tend to have more substance (although not always). And I love the salt and pepper handsome daddy type.
As someone of Chinese descent, I do get asked why there is a great number of Asian-White couples where early 20 something young Chinese men pair up with 65+ white men. I can only suppose a combination of daddy/granddaddy preference and desire for financial stability? Anyway, in your next article I hope you consider exploring sexual racism issues in the gay community with the title that people still use in personal ads: “No fats, femmes, druggies or Asians.”