Ask JT! I’m Old as Balls and Dating a Much Younger Man

Hi JT,

I love your column and love the advice that you hash out. I’m a bit of an older guy who has been single for almost 10 years, but know that maybe it is time to venture out there and find someone. I have had a few trysts throughout the years, hoping for something other than a rash or an STD to come out of those late night rendezvous’. My wish was answered, but I’m not sure if I’m doing the right thing.  

I’m 40 (about to be 41) in a few months. I work with younger people like yourself, and they keep me feeling so pumped and so energized. So I decided to get out there on the dating scene, and I met someone half my age. He was DA’ BOMB on all levels. He was maybe the politest person I’ve ever met, fairly good-looking, doesn’t smoke, and claims to be totally into fitness because he was an obese child.  Here I am a work-in-progress with some weight to lose and he was making me feel so attractive and so sexy. It was crazy.  

I just joined a gym, and these are things he knows and feels comfortable talking openly with me about.  He’s 6’4 (three inches taller than me) and buffed like he could bench press me a few times and not get tired, which made me feel even more turned on. Him talking about entering bodybuilding competitions was a bit much, but I can see myself with a big banner with his name or rubbing oil on him for a competition. With all that said, there is a catch: he is bisexual, or at least that is what he is telling me.  I’m not against bisexual men, but I’m not one to waste their time or mine getting involved because too many times prior I was completely in relationships with bisexual men and it didn’t end well at all.  

This young man has a gal living with him for financial reasons (something else he told me) and they’ve only been dating for two months.  He was honest and truthful about his life and even his sex life with this girl but that was during our pillow talk. He and I have been texting like crazy and talking on the phone but now it seems that he might be another friend with benefits on his terms.  What do I do, JT?

Old, Crazy Head in Love

Wow, there’s a lot to tackle in this question. On my first read-through I knew we had to take on realistic expectations of someone who’s currently living with and boning someone who isn’t you. Then I read it again and realized we should also address bi-phobia and your totally unnecessary “old” identity.

So let’s dig in, shall we?

I had to edit your letter way down for space, OCHIL, but I want our readers to know you spent a lot more time than see here expressing that you are, in fact, old as balls.

Well, I got good news for you, dude. 41 ain’t old. You’re not going to be the youngest guy out at the club, sure, but really, who wants to be? You’re also not going to be the oldest guy at the club, so as all those fabulous young people say (or said, ten years ago), you can chill-lax.

And here’s the thing about age: it really is what you make of it. I have friends in their 20s and 30s, and friends in their 40s and 50s, and I don’t really think too much of that disparity. And there’s a lot to be said about having a few years of experience under your belt, because one of life’s truisms is that often the older a person is, the more likely it is they have their shit together. Not to make it about me (except I’m totally about to), but there’s a great example of that right here on When I started writing my first column called SGM Seeks LTR in NYC, I was in my 20’s, single, working very unsteadily, and desperately flailing about for someone to love me for the bundle of neuroses and nerdistry that I am. Now, I’ve …

… I’ve …

(deep breath)

… crossed the threshold into my in my 30’s …

(okay, that wasn’t so hard)

… and I’ve got a nice, steady job, a fabulous side job working right here on TheBacklot, and I’m living in domestic bliss with my wonderful boyfriend, Morris. See? “Age” sometimes equals “shit together.”

Now, onto your guy. I’m going to cut right to the chase: his being bisexual is not a “catch,” and your calling it that says a lot more about you than it does about him. I don’t want to jump on you about this, but I do want to make this clear, because I’ve heard this from other gay men who write in to me, and it drives me crazy. A lot of gay dudes point to their poor track record with bisexual men and blame the other dudes’ bisexuality on the relationships not working out.

However, what is significantly absent from their reasoning is the fact that obviously their relationships with other completely gay men didn’t exactly work out either, or else they wouldn’t still be single.

You see the faulty logic there? Okay, moving on.

What is a catch, however, is that he’s currently in a relationship right now. I know you like the guy a lot – he sounds great – and you probably want him all to yourself, which it sounds like anyone would. (A hot bodybuilder who’s the politest guy you’ve ever met? Seriously??) But it sounds like A) that’s not in the cards, and B) he’s been as upfront with you as possible about that.

He’s living with someone who he’s also getting his bone on with. So as hot as the sex you’re having with him is, it’s not the only sex that he’s having. And it doesn’t sound like he’s made any indication he wants to change the status quo.

So you have three choices:

1) You can enjoy the hot sex with this Thanksgiving feast of a human being, soak in the fact that he really likes you and gets a lot out of what you have, and accept that he won’t be completely yours, or …

2) Explain to him you’re looking for a long-term, monogamous relationship and move on, or …

3) Explain to him you’re looking for a long-term, monogamous relationship, but will continue having hot uglies-bumping sessions with him until you do.

What’s most important is you do what makes you happy and satisfied, and treat him as kindly as possible. Remember, no one’s done anything wrong in this situation. All you can do is figure out the path that will make both of you the happiest and cause the least amount of bruised feelings.

Hey JT,

I met this guy a few weeks ago through friends, and we hit it off really quickly. He’s so sweet, smart, handsome, kind of shy (which turns me on), and into the same things I’m into. There’s just one major issue that I can’t get past: he is COVERED with tattoos. I’ve always said I would never date a guy with one tattoo, let alone tattoos that cover both of his arms, his chest, and his back. It just grosses me out so much.

I really like this guy, but I’m pretty sure this is a deal-breaker for me. But now it’s awkward, because we’ve gone out a few times and hooked up once. And I want to see him again, but I’m still grossed out by the tattoos. So what do I do?

Anti Tats

Okay … so tattoos totally gross you out, but not enough that you don’t go out with this guy a few times and end up in a naked roll so you can see just how many tattoos he has?

Something doesn’t add up here, AT, and it’s not this fella’s ink. It’s you, dude.

You tell me you vowed to never date a guy with tattoos, and yet here you are, doing just that. You say this tatted up guy meets all of the desirable qualities you’re looking for, save one – unaltered skin – yet you rattle off a list of totally sexy traits he possesses.

My gut instinct? I don’t think this is really a deal-breaker for you. Usually, if something will absolutely rule out if you’re willing to date someone, you know right away. You’re not “pretty sure.” You just know.

A lot of people have a very specific type of person they see themselves with, and as time goes on they cement this idea more and more in their head, making it very difficult for a real, live person with dreams and opinions of their own to fit into that mold. My advice to you would be instead of viewing his tattoos as an absolute roadblock, view it as a challenge to your preconceived notions of what you find attractive.

Work on expanding what you define as sexy, and you might find that this guy really is a keeper. Something about him made you go out with him and want to get his clothes off, so clearly there’s a limit to how much tattoos really gross you out. Go out a few more times and find out more about the man beneath the ink, and you just might discover tattoos are nowhere near the deal-breaker you thought they were.

Hey JT,

Okay, I’ve binged my way though Nikita, Alias, The Continuum, Lost Girl, Torchwood, Buffy, and Angel. What is a gay action fan to do now?

Lost Boy

Simple. Arrow.

Not only is that show kick-ass reinterpretation of a comic superhero, but it A) actually works and B) is an awesome show.

The first season is streaming now, so you can get all caught up. The lead, Stephen Amell, who before this was only known as the guy with the shiny butt in Dante’s Cove, is crazy sexy and actually seems to be doing a lot of the stunts himself, all the while providing plenty of shirtless eye candy. And there are a few kick-ass ladies in there as well, and everyone knows how much we ‘mos enjoy our brassy dames.

And at some point, I’m going to sit down and try to figure out why Marvel tends to dominate on the big screen, while DC seems to rule on the small.

But I digress. Oh, did I mention the best part about Arrow? You can totally check out our recaps here written by the ever-awesome Chris O’Guinn.


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