It was just shy of three months from when I finally admitted to myself that I was gay from when I moved to New York City.  So not only was I coming to the city to start my big time career ambitions, but also my big new gay life.  Knowing little about what to expect, I came to just accept that, based on the scene I fell into, I wouldn’t feel cute enough, wouldn’t have the right clothes, and could only hope that I would get an invite to visit a Fire Island Pines house as I surely couldn’t afford it.  (Which never happened.) But after unsuccessfully fitting in with mainstream gay culture, I met the love of my life and stopped caring what other boys thought of me.

About two years into our being together I suggested we go to Provincetown, Massachusetts for the weekend.  I had spent summers on the Cape during school but never stayed overnight in the “gay town” at the end of the earth.  We went, and by coincidence it turned out it was the end of something called “Bear Week”.  At the time, we thought a bear was simply an animal that well… shit in the woods.  Let’s just say that despite living in New York, I hadn’t yet realized that not everything from our culture had in fact ended up in an episode of Queer as Folk.  Bear culture… what’s that?

So in this weekend of firsts I met not just bears, but cubs, muscle bears, and daddy bears.  I found out that there was a bear flag, a bear themed magazine, and that you can sexualize chest hair.  (Woof!)  And on day two one particularly friendly “bear tracker” (a skinny hairless guy that none-the-less had a penchant for pelt) said to me quite seriously:

“You know what you are?”

“Ah… what’s that?” I replied warily.

“You’re an Otter.”

“I’m sorry?”

Dear Kirk,

I’m an older, average-looking bear who’s attracted to young, beautiful muscle studs. I haven’t had sex in a long time, because there just aren’t any guys that turn me on that are into me. I wish my standards weren’t so high, but I just can’t bring myself to be more attracted to other types of men. I had a sweet, decent looking skinny young guy come onto me recently and I really wanted to try and pick him up, but I was afraid that it just wouldn’t work for me. How can I open up my attraction to younger men that are just average, like me?

Dear Average Joe,

You have the kind of cooties that a lot of people have. Not just gay men, either. Tons of people are fixated on unrealistic standards of beauty. You’re not alone in this. There’s no harm in being attracted to muscled young hunks, but if it’s to the exclusion of everyone else, you’re writing yourself a prescription for misery.

I think we are disturbing our capacity for sexual attraction by constantly immersing ourselves in porn that features only guys with the kinds of bodies that we find exhilarating. Whether our trip is hairy bodies, masculine guys, muscle guys, skinny twinks, blondes, Asian men, African American men, Latino men…it’s great to have things we like. It’s not so great to be confined by our narrow checklists.

You say you haven’t had sex in a while because you can’t find a guy you’re attracted to who fits your standards. You have some choices. You can wait it out, seeing if you can find someone who will come along who fits your criteria and is also attracted to you. Darwin would probably argue that you need to adapt to your situation. It’s wishful thinking that there’s going to be a stream of beautiful young muscle studs who have no hangups about having sex with you. If you have strict standards, these younger guys who spend lots of time working on their bodies are likely to have some of their own.

You could hire an escort who conforms to your standards. You could hire an escort who’s outside your normal range of attraction and, if he’s intuitive and smart, he might be able to help you work through some of these issues.

Dear Kirk,

While I have enjoyed many wonderful encounters from this and related sites, ones that cater to an older/younger audience, I sometimes feel that I am either misleading or dishonest.  Recently, I met a young man and we began an email conversation.  He always referred to me in his mail as "sexy daddy" and we ultimately met.  Now, I realize he only wanted a "daddy" type for play, nothing more and I can deal with that. Yet, I find I am not comfortable with the daddy label for myself even if it accurately describes who I am, especially in the eyes of the young.

I have many friends in long term relationships who are of the older/younger milieu and who are completely happy together.  When I am around them, I sense how right they are for each other even when separated in age by 30 years or more.  Nevertheless, I so often feel that I am not a real person in their eyes but one they have conjured up that suits their fantasies.   In short, I don't need to be real---just OLD

I understand the attraction, the chemistry aspects of any sexual allure, and my fondness for younger guys never wavers.  I would appreciate your thoughts and any suggestions of how I may alter my profile to be more accurate about my tastes.  I tend to have a way with words---perhaps all the wrong ones!

Dear Uncomfortable Daddy,

Thanks for your astute and honest letter. Intergenerational dynamics are indeed complicated. Roles like daddy/boy, master/sub and man/puppy only scratch the surface. And there are lots of guys attracted to intergenerational mates who have no interest in any of these roles.  There are lots of guys who have no interest in taking on family roles;  there are guys who have no interest in being dominant or submissive. Some of us just like guys who are older or younger.

Dear Kirk,

My boyfriend and I have been seeing each other for 6 months and we’re talking about opening up the relationship so that we could have a three way.  We’re both a little jealous, but I’m more jealous than he is. I’m twenty years younger than him and the three way thing was his idea, which makes me wonder if he’s losing his attraction to me. I’m scared he’s going to be more attracted to some younger, hotter guy. Plus, we’re attracted to totally different guys. How could we possibly settle on a single guy? Do we take our ideal ages and average them together?

Do 3 Bees Make Sweeter Honey?

Dear Reluctant Swinger,

OK, I’m going to risk pissing off the entire gay movement here by saying that this whole business of marriage and monogamy is contrary to our nature. While being gay is genetic, having a single mate for the rest of your life, or even for a certain period of time, is a choice. That’s not to say it’s a bad thing to be monogamous. Monogamy can be a great way to bond with someone or a container wherein you can increase intimacy. I support monogamy when it’s a conscious choice, but I resist it when it’s the expected default setting.

Dear Kirk,

My husband and I are getting ready for another Christmas. We’ve been together 5 years and we’ve never had a good Christmas. He always gets depressed during the holidays thinking about his first lover, who died  in 1987 when I was in middle school. I feel like he hasn’t let go of  him. I grew up in a house where Christmas was a happy time. I want my husband to wear a Santa suit and get into the spirit of it all.

Dear Santa's Neglected Elf:

I’m sure your hubby would look hot in that Santa suit, but Christmas is a complicated time of year. The sunlight has disappeared and people are chemically depressed. It’s a good time to take an amino acid supplement to help your brain. Drink a tablespoon of apple cider vinegar each day to balance out all the holiday sugar. An 85 year-old friend taught me about vinegar. It works.

You and I are part of a younger generation who barely missed the ravages of the AIDS epidemic. We’ll never know what it was like to have a mysterious plague come in and wipe out loved ones. It was a holocaust. There are times I get overwhelmed by my partner’s nostalgia and memories. But I’d much prefer that he keep these loved ones alive in his heart – he’s a deeper and kinder man because of the epidemic.

It actually makes sense to be reflective during the holidays. There’s a somber quality to most winter traditions, whether it’s the Christian story of a poor pregnant woman being turned away from inns or the Pagans yearning for the return of the sun. As much as you can, allow your husband this time to remember his partner and friends. Is there a way you could build that into some new traditions you make together?

Dear Kirk,

I have never paid much attention to how old people are. If people ask me to guess their age, I am completely stumped. It has just never registered much with me. I notice whether a guy is in good shape, whether he’s cute, and most of all how he treats other people, me included. But I’ve noticed since I hit my early 40s that I get hit on by lots of younger guys -- I mean 10 or 15 or even 20 years younger. I am very flattered -- who doesn’t like attention? -- but I have also realized lately that it is hard to communicate sometimes.

I don’t mean sex -- on the times that it comes to that, I feel that I can really connect with the guy I’m with. I mean the other times, socializing together or going out to dinner or walking and having a conversation. I find that a lot of the references I make -- to music or movies or famous writers or other people -- elicit a blank stare -- younger guys just don’t have any idea who I’m talking about.

I hate trying to explain things. Usually I just end up feeling stupid about wasting five minutes on some boring story about somebody I think is “famous”. What should I do?  Signed -- Billy Pilgrim

Dear Billy,

I never play the game of guessing people’s age, because you’re always going to come up with the wrong answer. If a 50 year-old man asks you to guess his age, he wants you to guess 43 whether that’s warranted or not. If you say 47, he’s mildly disappointed he isn’t pulling off 43. And if you guess 50, he feels like he’s doing something wrong, since this is a culture where it’s not okay to look your age. And if you guess 54, he might throw a beer in your face. So good for you for not playing that stupid game. It’s in that genre of things one should only do in a bar, like folding napkins into bunnies.

You have a different set of cultural references than the younger men you’ve been dating. It’s understandably frustrating to you that these guys give you a blank stare when you mention a movie that maybe changed your life. As a younger man, I’ve received my share of blank stares from older men.

Here’s the tricky thing. The younger men in an intergenerational relationship often get smarter from being in that relationship. We’re expected to keep up with two cultural currents – our own and that of our partner. I have seen a lot of movies and read a lot of books because older men point to them as cultural touchstones. But I can also tell you the third song on Nirvana’s album “In Utero.” I can quote Winona Ryder’s lines from the movie “Heathers.” And I don’t expect older men to be able to do that or even appreciate that. And if I show them one of the movies I loved as an adolescent, I don’t expect them to like it. I show it to them because it helped form the person I’ve become.

Sometimes I find that there is a double standard around this: I’m expected to know all the cultural references from my generation as well as from an older partner’s generation, while the older partner isn’t as invested in learning the cultural references that followed theirs. This isn’t always the case, but I’ve seen it enough that I’m saying it out loud.

I’ll let you in on a younger man’s secret: it’s super annoying when an older man acts shocked that you don’t know who sang the obscure girl group song that comes over the stereo when you’re at Safeway. How can you not know who this is?! No matter how many times it happens, he seems genuinely perplexed that you weren’t at summer camp with him in 1966, hearing that song for the first time. And it can be worse if you’re in a group of older men and someone makes a movie reference: He’s a mere child! You haven’t seen that movie? You don’t even know who Alfred Hitchcock is, do you! Making repeated jokes about a younger guy’s age can make an older guy come off as obsessive, youth-fixated and desperate. By the same token, younger guys who take insensitive potshots at older men for being “out of touch” should get smacked upside the head.

My boyfriend and I approach this issue with a lot of care. We’re both interested in seeing and experiencing the best that the world has to offer. Being in a relationship, especially one that’s intergenerational, is a huge advantage because you have two cultural filters at work. I expose him to things that strike me as interesting and he does the same for me. That way, we’re both smarter and we never get bored.

Dear Kirk,

I have always been attracted to older guys. Even in high school I always hung out with seniors, even when I was a freshman! Now I have graduated from college and started a professional life in a big city, and I have gotten into a relationship with an older man. He is 42, and I am 27.

We’re totally in love, and the sex is wild and great. We’ve been together for eight months now, spending basically every night together.

The problem is that we always stay at his house because I have roommates, and now he wants me to move in with him. I understand completely why he doesn’t want to stay at my place with my roommates hanging around. But I also feel weird about moving in because I don’t want to be someone who takes advantage of the fact that he’s farther along in his career and has more money and even owns his own house. I’ve known some guys who were “kept” by older (or just richer) men, and I don’t want to be one of those.

This guy is really wonderful and I don’t want to lose him or appear ungrateful or push him away, but I just don’t know what to do.

 Dear Real Estate Victim,

Not to minimize your concerns, which is an actionable violation of the laws of Social Work 101. but hey, there are worse problems to have! You’re fresh out of college and you’re in love with a man you’re having great sex with. Rejoice, first of all.

In celebration of the opening of the new movie "MILK", we are excited to share this amazing piece by Steve Beery. Steve was a writer and gay activist who died of AIDS in '93. He met Harvey Milk when he was 25 years old and Harvey was 48. Harvey was a daddy who definitely appreciated younger men. This piece was provided to us by Armistead Maupin (my wonderful husband), who met Steve at Harvey's memorial service and remained his closest friend until his death.

My Month with Harvey

by Steve Beery

I was suffering from a typical San Francisco ailment – costume claustrophobia. My tights were riding up, my fake-satin cape was itchy, and beads of sweat were rolling down behind my eye mask. I was dressed as Robin the Boy Wonder at the 1978 Beaux Arts Ball, and I was being unmistakably cruised by a man I knew but had never met.  The man was Harvey Milk, the first openly gay city supervisor – a man I respected and admired.

We’d smiled and nodded on Castro Street several times that year.  I like Harvey’s wide-open grin, and I’d wondered whether the attraction was mutual.  Now it looked like maybe it was. Nervously I straightened my cape, checked my trunks, adjusted my gloves. The supervisor, at ease in his rumpled grey suit, extended his hand and uttered the corniest pick-up line imaginable. “Hop on my back, Boy Wonder, and I’ll fly you to Gotham City,” he said, almost keeping a straight face.

The line was corny, but effective. Harvey had a gift for persuasion, a way of making you believe he could do anything. We swapped phone numbers and got together the next night.  The thing that impressed me most was his laugh, explosive and uninhibited; that, and the slightly daffy look in his eyes, like an overgrown kid’s. At 48 he was nearly twice my age, but full of boyish mischief.

It didn’t take me long to realize that Harvey was a nut, a screwball, a wild card. He was also a satyr, a gleeful disciple of Eros who’d found a way to marry his essential craziness to a set of well-ordered work habits. He insisted on being on call to his constituents 24 hours a day. No problem – from towed cars and trash pickup to tree pruning – was too small. Despite his hippie, flower-power, Summer of Love experience, there wasn’t an ounce of “California mellow” in Harvey. His native New York aggression, undiluted by the amiability of Castro Street, was always spoiling for a fight.

I was surprised, on our first date, to find out how strong he was.  He didn’t have a gym-toned body; he was built more like a big bull, rangy and muscular.  Within his first two minutes at my apartment he picked me up and dumped me unceremoniously on my bed.  He liked to do things fast, at double speed. He walked fast. He talked fast. He even ate fast.

Dear Kirk,

My boyfriend and I have been together for six months. He is 23 and I am 48. I’m a college professor and he works at Costco as a re-stocker. I make about three times what he makes. I often end up paying for dinners out and recently paid for a weekend vacation. I want him to finish college and get a better job but he hates school and doesn’t want to do it. We are talking about him moving in to my house, so I need to set some boundaries about money and don’t know where to start. 

Dear Sugar Free Daddy,

Money is powerful, powerful stuff. I think of it like an open flame – it can be harnessed to cook your meals and keep you warm, but it can also burn the shit out of you. Anxiety about money has derailed millions of relationships.

It sounds like you guys are just getting to know each other. You’re working with a number of potent differences: age, financial status, educational background and probably a bunch of others. Tread lightly and always keep in mind what brought you together in the first place.