Hi Jake,

A few months ago, I started going to a progressive church that’s welcoming to queer people. It’s been nice, because I’ve always enjoyed practicing my faith, and I finally feel free to do so. I go to Mass every Sunday, hand out programs before the service, and volunteer at various church events.

That’s where my problem started.

There’s a married guy who volunteers too. Wife, two kids, the whole deal. He’s completely straight. But the thing is, it seems like he really enjoys gay-baiting me.

Hear me out. He’s constantly making comments that feel just flirty enough to make me wonder if he’s interested, like pointing out how good-looking certain guys are. Then he’ll randomly text me shirtless beach photos. One was even a bathroom selfie where you could clearly see the top of his pubes!

When we’re volunteering, he seems to go out of his way to get close to me. Last week, we had a church car wash, and he literally spent half the time lathering himself up with soap and laughing right next to me while wearing a skimpy bathing suit.

If that’s not gay-baiting, I don’t know what is.

The weird part is, I don’t even think he’s secretly closeted. Another gay guy at church told me he’s acted like this before. Apparently, he likes the attention and gets an ego boost from knowing gay men find him attractive. Maybe he isn’t getting that kind of validation at home.

Regardless, it’s driving me crazy. He’s attractive, he seems to enjoy whatever game he’s playing, and I’m the one left feeling hot and bothered over someone who isn’t available.

So what am I supposed to do here? Gay-baiting feels so subtle that it isn’t exactly something you can file a complaint about. Do I call him out? Keep my distance? Or just accept that I’m being played?

Hook, Line & Sinker

Dear Hook, Line & Sinker,

Traditionally, the term “queer-baiting” (or “gay-baiting”) has been used to describe celebrities, influencers, or companies that hint at queerness to attract LGBTQ+ audiences without actually identifying as queer. You’re describing something similar, but on a personal level: someone who seems to enjoy creating just enough ambiguity about his sexuality to keep you wondering what’s really going on.

Whatever label you put on it, that kind of teasing can be incredibly frustrating. Feeling like someone is dangling the possibility of something that was never really on the table can leave you annoyed, confused, and maybe even a little used.

It’s certainly possible this guy enjoys being desired. Plenty of people do. It feels good to know when someone finds you attractive, and for some, that validation can become addictive. Texting provocative pictures, making suggestive comments, lingering a little too close, and, of course, the soapy car wash performance are all ways he might be trying to draw you in. When you put it all together, it makes sense you’d be questioning his intentions.

But I’d also be careful about assuming you know exactly what’s motivating him.

Maybe he likes the attention. Maybe he’s an oblivious flirt with everyone. Maybe he’s testing boundaries. Maybe he’s wrestling with something internally. Or maybe he’s simply one of those people who enjoys being perceived as desirable without giving much thought to how confusing that can be for the person on the receiving end.

The truth is, you probably won’t know unless he tells you. And frankly, I’m not sure that’s the question worth spending the most energy on.

The more important question is this: What is this dynamic doing to you?

You’ve already answered that. It’s distracting you, frustrating you, and leaving you emotionally invested in someone you’ve already acknowledged is almost certainly unavailable. Fortunately, that’s the part you actually have some control over.

If he really is intentionally dangling the possibility of something that he has no intention of acting on, you don’t have to keep grabbing for the hook. And if he’s completely innocent and you’re misreading the situation, creating a little distance still protects your peace.

That doesn’t mean you need to confront him or make a dramatic announcement. In fact, I’d probably start much smaller. Stop engaging with the flirtation. Respond to the shirtless photos with the same enthusiasm you’d have for a picture of someone’s new lawn mower. Keep your conversations friendly but a little less personal. Give your attention to people who are actually available rather than someone who keeps you guessing.

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Your responsibility isn’t to figure him out or set him straight. Your responsibility is to protect your own peace. The rest? He can save for Confession.

Ask Jake a Question

If there’s something on your mind, send it to jake@askjaketherapy.com

Your question may be part of a future Ask Jake, answered anonymously.

And if you’re looking for a queer therapist who actually understands what you’re dealing with, you can find one at LGBTQTherapySpace.com.

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Hi Jake,

I’m about to turn 32, and sometimes I look at my romantic history and just… sigh. It’s basically nonexistent. I’ve never been in a relationship, and I’ve only had less than 10 partners in my entire life—and those were mostly friends, not people I met through dating or hookup apps. Most of them are now in relationships, live far away, or are just unavailable. I don’t have a network of gay friends or prospects, and honestly, I wouldn’t even know where to start building one.

It’s not that I haven’t wanted connection—I just feel like I somehow missed a crucial window for developing the skills or confidence to pursue it. And now, at 32, I’m wondering if something’s wrong with me. Have I fallen behind? Do I need to “boost my numbers” just to catch up and feel like a well-rounded, dateable adult?

I can’t help but feel underdeveloped—like I’ve missed the gay version of puberty. Am I just late to the game, or is this something I need to fix?

Notchless in Seattle

Dear Notchless in Seattle,

Notches on the bedpost do not make a gay man. If they did, we’d have a lot of so-called “experienced” men walking around who’ve never developed a real sense of emotional intimacy, communication skills, or the capacity to build a healthy relationship. Romantic prowess is not the same thing as emotional maturity—and racking up partners doesn’t automatically mean someone knows how to be present, vulnerable, or connected with another person.

I’ve known people who’ve had dozens—sometimes hundreds—of partners, but still freak out at the first sign of real intimacy. They can flirt, charm, and hook up with ease, but the moment something feels emotionally vulnerable, they shut down. Others jump from relationship to relationship without ever slowing down to ask what they truly want or need. They’re technically “experienced,” but they keep reliving the same patterns—confused, frustrated, and wondering why nothing sticks.

What you’re describing isn’t a failure—it’s a different timeline. And in our community, where so many of us didn’t get to experiment or date freely as teens or young adults, different timelines are more the norm than the exception. It’s just that no one really talks about them.

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Hi Jake,

I moved into a new apartment about a month ago after meeting my roommate online. One of the reasons I chose his place was that we’re both gay, and I thought it’d be nice to be open about that part of our lives.

Turns out, I got a little more openness than I bargained for.

He has a certain habit that comes with a really annoying, honestly unsettling noise. On my second night in the new place, I started hearing a “swish, swish, swish” coming from his room. I figured it was something with the air conditioner or maybe a fan. But I soon realized this was a different kind of appliance, and definitely not one sold at Home Depot.

I’m now 99% sure my roommate is in a serious relationship with his Fleshlight... and the sound it makes carries all the way through our shared wall.

The problem is, I love the new place, and everything else has been great. But this happens almost every night, and it’s driving me crazy. I’ve started dreading bedtime because I know there’s a good chance it’ll wake me up if I manage to drift off.

Now, I don’t know how to bring it up. If I’m honest about what I think the noise is, I’m afraid he’ll think I’m prudish or judgmental and decide he’d rather find another roommate. And if I try to be vague about it, I’m afraid I’ll still embarrass him, which will make our whole living situation uncomfortable.

How can I get him to stop without embarrassing him or making him resent me?

I’m Wide Awake

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Dear I’m Wide Awake,

Living with a roommate means learning more about another person’s habits than you ever wanted to know. Usually it’s their questionable taste in music, their shower schedule, or the fact that they apparently own a blender with only one setting. Occasionally, though, it’s something a little more… personal.

Here’s how I see it. I don’t think this is actually a conversation about masturbation. It’s a conversation about boundaries. More specifically, it’s about what happens when someone’s private behavior stops being entirely private because it interferes with someone else’s ability to live comfortably in their own home.

Your roommate isn’t doing anything inherently wrong by watching porn, using a sex toy, or masturbating. Solo sex is healthy, normal, and none of your business.

The noise, however, is.

But here’s what I found most interesting: it seems you’ve spent far more time thinking about how your roommate might react than about simply asking for what you need. Before you’ve said a single word to him, you’ve imagined him deciding you’re prudish or judgmental—or even that he’d rather find a new roommate. That’s a lot of emotional energy spent trying to manage a conversation that hasn’t even happened yet.

One of the hardest parts of setting boundaries is accepting that you can’t control how another person interprets them. You can be kind, respectful, and choose your words carefully. But you can’t guarantee someone won’t feel a little embarrassed or defensive.

That’s okay. A little awkwardness is often just part of living with other people.

So don’t make this a conversation about what he’s doing. Make it a conversation about sleep.

I’d say something like: “Hey, can I bring up something a little awkward? I’ve been hearing some noise from your room most nights that’s been waking me up. I honestly don’t care what you’re doing in there, but I was wondering if there’s any way to keep it a little quieter.”

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Notice what that does. It doesn’t accuse him, shame him, or even mention the Fleshlight. It simply explains the impact his behavior is having on you.

If he guesses what you mean, that’s okay. You’re roommates. Sometimes sharing a home means having conversations that neither of you would choose to have.

The irony is that you’ve spent weeks trying to protect him from a few minutes of awkwardness while sacrificing your own comfort. That’s a trap many of us fall into, especially if we spend a lot of energy trying to keep everyone else comfortable.

Wanting a good night’s sleep doesn’t make you a prude. It makes you a good roommate who’s asking for a reasonable boundary. Here’s hoping everyone experiences a little less… friction.

Ask Jake a Question

If there’s something on your mind, send it to jake@askjaketherapy.com

Your question may be part of a future Ask Jake, answered anonymously.

And if you’re looking for a queer therapist who actually understands what you’re dealing with, you can find one at LGBTQTherapySpace.com.

Photo by Usman Yousaf on Unsplash

Hi Jake,

My boyfriend grew up in Mississippi and insists we need a gun in the house to protect ourselves as a gay couple. I hate guns and don’t even want one under my roof.

The confusing part is I kind of get where he’s coming from. Growing up in the Deep South, he was bullied for being gay, called slurs, and often felt like he had to watch his back. He says those experiences taught him that the world isn’t always safe for people like us.

Now, whenever there’s a story about another anti-gay hate crime, he brings up getting a gun again. His argument is that he’d rather have one and never need it than need one and not have it.

I see it differently. To me, bringing a gun into the house would make me feel less safe, not more. I worry about accidents, impulsive decisions during moments of anger or drunkenness, or it being taken and used against us.

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We’ve been arguing about this for weeks. I know he thinks I’m being naive about how hostile the world can be toward people like us, but I think he’s letting his fear get the better of him. Neither of us seems willing to budge. He can’t understand why I wouldn’t want us to have a way to protect ourselves. I can’t understand why he’d want a gun in our home, knowing it’s going to make me uncomfortable every single day.

So I guess my question is, is this the kind of disagreement we can work through, or is it one of those things where we’re just fundamentally incompatible?

Feeling…Triggered

Dear Feeling…Triggered,

I don’t think this is really a disagreement about guns. I think it’s a disagreement about safety.

Your boyfriend grew up in a part of the country where being openly gay had legitimate risks. He probably learned early on that not everyone would be accepting, and that sometimes the safest thing to do was stay alert and prepared. Experiences like that don’t simply disappear because you become an adult or move somewhere else.

And while acceptance has increased dramatically over the past few decades, we’ve also seen a recent rise in anti-LGBTQ rhetoric, political attacks, and public hostility. It’s not hard to understand why many LGBTQ people feel less safe and less accepted today than they did just a few years ago.

When people feel threatened, their natural instinct is to protect themselves and the people they love. Your boyfriend believes a gun is the best way to do that. He’s probably reacting not only to today’s political climate and headlines, but also to every locker room he had to endure, every homophobic dig he brushed off, and every other experience that taught him that being openly gay could make him a target.

None of that makes your reaction unreasonable, though.

For you, the gun itself feels like the threat. The very thing that makes him feel safer would make you feel less safe. That’s the paradox at the heart of your disagreement.

When couples reach an impasse like this, arguing harder rarely helps. Instead, I’d encourage you to get curious about what safety actually means to each of you. Try to understand each other’s fears before trying to convince each other who’s right.

When your boyfriend imagines having a gun, what fear is he trying to calm? When you imagine a gun in the house, what fear gets activated in you? Is there another way your boyfriend could feel safer without a gun? Is there perhaps a way you could feel safe with one in the house? Are there alternatives that address either of your concerns without violating the other’s boundaries?

The goal isn’t necessarily to change each other’s minds. It’s to understand each other better.

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Sometimes those conversations soften our positions. Other times, they reveal a compromise that wasn’t obvious before. And sometimes, they clarify whether a disagreement is bridgeable...or not.

The good news is that the two of you aren’t fighting because one of you doesn’t care about the other’s well-being. Quite the opposite. You’re both trying to create the same thing: a life where you both feel protected. You just have different ideas about how to get there.

The challenge is figuring out how to build a home where you can both let your guard down.

And if you can’t, that’s not necessarily a sign that either of you is wrong. It may simply be a sign that you’ve discovered one of those rare issues where love and compatibility aren’t always the same thing.

Ask Jake a Question

If there’s something on your mind, send it to jake@askjaketherapy.com

Your question may be part of a future Ask Jake, answered anonymously.

And if you’re looking for a queer therapist who actually understands what you’re dealing with, you can find one at LGBTQTherapySpace.com.

Photo by Tom Def on Unsplash

Hi Jake,

So, I had an experience on Sniffies the other night that still has me shook.

I met up with this white guy whose profile said he was into “role play.” I didn’t really know exactly what that meant, but I’m pretty open-minded, so I figured I’d give it a go.

The first thing he did when I arrived was comment on my race. He told me I was a “really strapping Black man,” which immediately made me uncomfortable, but I tried not to read too much into it.

Then he told me he wanted me to pretend that I had just escaped from prison. At first, I thought he was joking, but he insisted that I act out being an escaped convict on the run who had stumbled to his house looking for a place to hide and would do whatever he asked in return. When I looked at him in disbelief, he was like, “What? It’s just a fantasy. No big deal.”

The problem is, as a Black man, this really did not sit well with me.

I’ve spent my whole life dealing with stereotypes that paint Black men as thugs, criminals, or low-lifes. It felt less like he was seeing me as a person and more like he was reducing me to a fetish. Maybe that wasn’t his intention, but it sure felt that way to me.

Part of me wonders whether I was reading too much into it all. But if you’re asking someone to participate in a fantasy that’s wrapped up in a lot of history, shouldn’t you understand why they might not find it sexy?

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I quietly excused myself and left. But now I’m wondering: Did I overreact? Was there some other way I should have handled this?

Wrongfully Convicted

Dear Wrongfully Convicted,

Um, no, I don’t think you overreacted. I think you handled this exactly the way people should handle sexual situations that suddenly stop feeling sexy: You listened to yourself.

One of the strangest things about dating and hookup culture is that we often feel pressure to justify our discomfort as if we’re presenting evidence in court. We start asking ourselves questions like: Was he really being racist? Was he fetishizing me? Did he mean it that way? Sometimes those questions matter. But they aren’t always the most important questions.

The more important question is whether you wanted to participate. You didn’t. That’s enough.

Could this guy have viewed the whole thing as an innocent fantasy? Sure. Human sexuality is weird. People fantasize about all kinds of things that have little to do with what they consciously believe in everyday life.

But here’s where I think he made a mistake. The moment he invited another person into that fantasy, it stopped being just about him.

Whether he intended to or not, he asked a Black man to participate in a fantasy that drew on stereotypes carrying a whole lot of baggage. Once another human being is involved, their experience matters too. You don’t get to tell someone that a fantasy is harmless after they’ve already conveyed that it isn’t.

And let’s be honest: the prison fantasy wasn’t the first thing you heard. Before that, he was already commenting on you being a “really strapping Black man.” Then came the escaped-convict storyline. It’s not hard to see why those two things felt connected.

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We’ll never know exactly what was going through his head. But I don’t think that’s the real issue. The real issue is that the entire encounter left you feeling more like a character than a person.

You showed up looking for a connection, however casual. Instead, you felt like you’d accidentally walked into somebody else’s bizarre casting call, a role that had way less to do with who you are and more to do with what he wanted you to represent. That’s not a great foundation for intimacy, even the casual kind.

I also want to point out that leaving doesn’t automatically mean you’re condemning someone as a bad person. Sometimes it simply means you’ve discovered that the two of you have very different ideas about what’s sexy, playful, or acceptable. You’re allowed to decide that a particular fantasy isn’t for you without needing to prove that the other person had malicious intentions.

And for what it’s worth, I think you handled this situation with a lot of grace. You could have shamed him, started an argument, or demanded an explanation, but you didn’t. You simply decided that this wasn’t a situation you wanted to be part of. That’s called having self-respect.

Ask Jake a Question

If there’s something on your mind, send it to jake@askjaketherapy.com

Your question may be part of a future Ask Jake, answered anonymously.

And if you’re looking for a queer therapist who actually understands what you’re dealing with, you can find one at LGBTQTherapySpace.com.

Photo by Abubakar Isa on Unsplash

Hi Jake,

I am a 28-year-old, professional gay man with a very specific liking for married straight men. Now, I know such guys (usually in straight relationships and on the DL) should be faithful to their significant other, I just feel it is almost a biological urge on my side to flirt with them if I think they are cute or if they show any signs of being bi-curious. I generally like the daddy-type of guys and even for porn, my preference is “married man cheating”. Should I feel guilty? Why do I have this predilection? Do I need to change?

The Caped Seducer

Dear The Caped Seducer,

I don’t think it’s healthy for anyone to have guilt around their sexual desires and predilections, as long as you are engaged in mutual affairs and are not harming anyone or breaking any laws. Let’s face it, it takes two to tango, so if you’re able to seduce these married, straight-identifying men, then you’re obviously tapping into an unfulfilled need they have to explore other sides of their sexuality.

Is it healthy for these men to have an illicit affair with someone (of any gender) behind their partner’s back without talking to them about it? Probably not. But this is a decision they are making, not you. Ultimately, if someone is cheating, the ownership of that is on them, not on the “manstress”.

That said, you bring up some good questions about where this naughty super-power comes from, and why you’ve chosen to cultivate your gift, Obi Wan Kenobi-style. You describe an almost “biological urge”, which to me, could mean that there is some psychological need being met by wielding your power. The best thing to do would be to talk to a therapist about this, and see if you can uncover where this might come from (if you don’t see your state listed, let us know!).

For example, perhaps you love the “conquest”, and when you achieve it, it provides some sense of self-worth or validation that you otherwise might not feel. Or, maybe it almost feels “dangerous” or naughty, and the adrenaline from the chase harkens back to when you were first exploring your sexuality and felt shame, guilt, or that it was “bad” in some way (yet oh so good) to explore your sexuality. It might not even be that deep, and you simply lusted after the straight “daddies” in the country club locker room as a teen, and that imprinted upon you a desire for a certain type going forward.

Regardless of its origin, the question you seem to ask is, “What do I do about it?” As RuPaul says, “With great power, comes great responsibility”, so it’s up to you to decide if there’s any harm in this behavior, and if you feel it would be better for you to let your power go dormant for awhile.

Are you limiting your own chances to find a healthy partner because you’re drawn to unavailable men? Does it feel “safer”, in some way, to know that there’s a shelf-life once your seducing power takes hold? Perhaps it feels scary to think about going after an available gay guy you’re attracted to, because you worry about rejection? Rejection might feel easier if it comes from a straight guy, because you can blame his sexual orientation, instead of yourself. Again, talking to an LGBTQ psychotherapist could really benefit your understanding of it.

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As far as if you “need to change”, that’s up to you. I often ask clients if the pros outweigh the cons. Are there any risks involved? Are you putting yourself in unsafe situations, such as the possibility of a scorned spouse enacting revenge on her cheating man, or a closeted guy wanting you to keep quiet from his secret shame? If you don’t sense any kryptonite, then I say, “What’s the harm?” Clearly your married daddies like themselves a piece of Clark Kent. Just don’t fly too close to the sun!

An Update from Jake on this letter:

After this column ran, I received a pretty intense comment from a reader who was deeply upset by the way I responded to the letter. They were shocked that I referred to the writer’s attraction to married men as a “superpower,” and accused me of condoning unethical behavior, blaming the married men entirely, and ignoring the responsibility we all have to act with integrity. They went as far as to say that I’m “not fit to give advice.”

That’s a hard thing to read—but also worth addressing.

So here’s my response: I hear you. I absolutely believe that ethics and accountability matter in all relationships—especially the messy, complicated ones. The tone of the column was intentionally playful, and the use of “superpower” or “caped seducer” was meant to mirror the tone of the letter itself, not to excuse deception or betrayal.

That said, if my humor got in the way of the message, that’s on me. The point I meant to make was that desire—especially desire rooted in taboo—can be psychologically complex. My aim was to explore why someone might repeatedly seek out unavailable partners, not to let anyone off the hook for hurting others.

The responsibility in situations like this doesn’t lie with just one person. The married man cheating is making his own choices, and those choices have consequences. But yes, the person knowingly engaging with someone who’s partnered also holds responsibility. That’s a piece I could’ve emphasized more, and I appreciate the reminder.

As always, I’m open to feedback—and to evolving the way I write about these layered topics. Thanks for holding me to a high standard.

Ask Jake a Question

If there’s something on your mind, send it to jake@askjaketherapy.com

Your question may be part of a future Ask Jake, answered anonymously.

And if you’re looking for a queer therapist who actually understands what you’re dealing with, you can find one at LGBTQTherapySpace.com.

Photo by Levi Meir Clancy on Unsplash

Hi Jake,

Since entering my 40s I’ve noticed something unexpected over the last few years: my type has changed!

I used to be exclusively into smooth, lean, athletic guys. Give me a swimmer’s build, and I was done for. In my younger days, Tom Daley was basically twink perfection. But lately I’ve weirdly found myself attracted to almost the exact opposite: dad bods!

I catch myself checking out guys with a few extra pounds way more than the ripped guys I used to lust after. If a guy has a little bit of a belly and some love handles, I find it very hot.

I’ve noticed something else, too. I’m not as self-conscious around these kind of guys. I don’t have to psych myself up to message them or feel nervous if I want to strike up a conversation.

So, now I’ve actually been wondering... Has my type really changed, or am I just finding it easier to be with guys who might not think I’m out of their league? Sometimes it’s hard to tell what’s true attraction and what’s just easier.

From Abs to Flab

Dear From Abs to Flab,

Believe it or not, attraction isn’t always frozen in time. What you liked 20 years ago may not be the same thing that gets you going today. As we age, gain more experience, and reevaluate priorities, preferences do sometimes change. This all might be as simple as that.

Think about it this way. If you suddenly discovered that chocolate ice cream had become your favorite flavor, you probably wouldn’t question whether it was “real.” You’d just eat the ice cream.

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So before we turn your attraction to Dad Bods into some grand psychological mystery, let’s acknowledge something: Dad Bods can absolutely be sexy.

There’s something undeniably attractive about a man who’s comfortable in his own skin and isn’t spending every waking hour trying to maintain perfection. There’s something attractive about a guy who’s comfortable being himself. And yes, there can be something comforting about a softer, fuller physique. More to love, as they say.

What turns us on isn’t always about abs and measurements. Sometimes it’s about warmth or relatability, or looking at someone and thinking, “Yeah, I’d happily curl up on the couch with him on a Sunday morning.”

At 25, you may have been looking for excitement, status, or validation. At 45, you may find yourself valuing connection, comfort, and authenticity a little more. Neither version of you is wrong.

So no, I don’t think your newfound appreciation for some extra weight automatically means you’ve lowered your standards or talked yourself into anything.

That said, I understand why you’re asking the question. And honestly, the fact that you’re even asking it tells me you’re trying to be insightful, honest, and curious about yourself.

It is true that, as gay men, many of us have become experts at seeking safety in a world that didn’t always feel safe. Part of that safety involves avoiding rejection. Sometimes it’s easier to go after someone who doesn’t make us feel quite so nervous. That doesn’t mean we’re settling. It just means we’re human.

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But that doesn’t mean your attraction isn’t real. I don’t think we should assume that safety and passion are opposites. Sometimes feeling safe is part of what makes someone sexy.

So yes, I think you should embrace your Dad Bod era and stop overthinking your attraction.

If a little belly and some love handles genuinely make your heart race, enjoy them. At the same time, if some ridiculously ripped guy catches your eye, don’t count yourself out with him either.

Dad Bods or not, you don’t need to keep putting your attraction on trial. You just need to make sure fear isn’t the one doing all the swiping.

Ask Jake a Question

If there’s something on your mind, send it to jake@askjaketherapy.com

Your question may be part of a future Ask Jake, answered anonymously.

And if you’re looking for a queer therapist who actually understands what you’re dealing with, you can find one at LGBTQTherapySpace.com.

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Hi Jake,

So, I have a type, and I’m getting tired of feeling like I’m supposed to apologize for it.

I’ve always been attracted to conventionally masculine men. Beards, body hair, muscles, gym bros, daddies, deep voices—the whole package. I like guys who look and act like guys. That’s what turns me on. It’s not something I chose, and it’s not something I’v…

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Hi Jake,

I’m in my late 40s, and while I don’t party like I used to (thank God), I still miss dancing to electronic music and feeling that collective pulse of gay men moving together. There was something transcendent about it — that mix of bass, sweat, lights, and connection. For a few hours, it felt like we could all be free.

These days, I think about going out clubbing again, but every time I picture it, I imagine being the oldest guy there, surrounded by twenty-somethings with much better bodies, and feeling like some tragic relic trying to relive his youth. I imagine people seeing me and thinking, “How sad… doesn’t he realize it’s over?” There’s just so much ageism in our culture.

Still, every now and then I’ll hear a song that used to play at Twilo or some long-gone after-hours warehouse, and I’ll feel it — that old ache for the experience returns. I do miss a lot about it. For me, going out wasn’t just about hooking up (though grinding on the dance floor was fun too); it was about being alive and connected and sexy and joyous. I miss that feeling deeply.

I feel like I’m missing out on a world I no longer have a place in. Is there a way to reconcile this?

Music Sounds Better with You

Dear Music Sounds Better with You,

I love how clearly you remember what those nights meant — not just the dancing, but the communion. What you’re describing wasn’t simply nightlife; it was an experience. For so many of us, the club was church, therapy, and family reunion rolled into one. We found each other there — sweaty, euphoric, anonymous, and free — and for a moment, the world outside stopped judging. It makes perfect sense that you miss it; you’re mourning a space that once held your aliveness.

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Hi Jake,

My boyfriend and I have been together for about four years, and six months ago, we decided to open up our relationship. Before doing so, we had an honest talk about rules, expectations, safer sex, and what we wanted. We ultimately decided that outside hookups were allowed as long as we were transparent about them.

A few weeks ago, a group of frie…

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Hi Jake,

My new boyfriend is amazing. We have great chemistry, he’s so fun to be around, my friends all love him, and he’s super sexy. I feel like I won the lottery! But there’s a catch...

He’s also very affectionate in public.…

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Hi Jake,

I’m self-employed and recently took a job as a personal assistant to a woman who works in the entertainment industry. It’s been about four months and she and I have developed a good working relationship, although sometimes she can be a little much.

For the most part, she treats me with respect, and claims to be very liberal/open-minded and an LGBTQ+ ally. I think she believes this, but there have been a few times now where she’s made off-handed comments that I’m not sure how to take.

For instance, she likes to refer to herself as a “f*g hag” and doesn’t seem to know that the phrase went out of fashion a while ago. She’s also said that she “doesn’t get” the whole “they/them” pronouns thing and she’s made passé jokes about bisexuals not being “real.” But what bothers me most is when she calls me “princess”. She literally sometimes introduces me to other people as, “This is my assistant. He’s my little princess.”

I think she thinks it’s a term of endearment, but I don’t think she would refer to me that way if I weren’t gay. I also don’t know how to address it with her since she’s my boss and it’s just me and her. There’s no HR department to go to. I would like to keep this job, but I also don’t want to constantly feel uncomfortable when she tries to be an “ally.”

The Princess Diaries

Dear The Princess Diaries,

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Hi Jake,

My husband and I started an online business together a few years ago as a side project. At first, it felt like a dream. He’s my best friend, so it was genuinely fun to work alongside him every day. Plus, neither of us had ever worked remotely before, so it felt surreal to be sitting by a pool in Puerto Vallarta with our laptops and cocktails whi…

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Hi Jake,

I’m a 75-year-old lesbian, and have never written to an advice column before.

But last week, I went to my Pride planning committee meeting and had a really awful experience with a younger gay guy who disagreed with me about something. He started snapping at me, rolling his eyes whenever I spoke, and calling me “out of touch” and “silly” in front …

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Hey Jake,

I turn 50 next month, and so I’ve been doing a lot of reflecting. For the most part, I’m happy with my life and proud of the choices I’ve made. Except for one thing. I’ve never been in a serious relationship. My longest one lasted about two years, and that was over a decade ago. I date and occasionally hook up (when I’m lucky), but I’ve never landed on “the one”, and I don’t know why. It’s certainly not for lack of trying. All my friends assume I’m happy being single since I never talk about my love life with them (mainly because I DON’T HAVE ONE!), but the truth is I never thought I’d be a 50-year-old bachelor, and I feel like I’ve missed out on something special. Everyone always says “50 is the new 40,” and I know there’s still time, but part of me regrets that I haven’t found anyone yet and that if/when I do, we will have missed out on so many great years together. Thoughts?

Fifty and Forsaken

Dear Fifty and Forsaken,

Milestones are often a time to reflect, so it makes sense that you’re taking stock of your life. A lot of people say turning the big “Five-O” is one of the harder birthdays to grapple with. Even though I believe there’s truth to the cliche that “age is just a number”, I understand that 50 may feel a little different. Some might feel their carefree days of youth are over, and they’re looking at what’s next, what’s truly important, and how they want to spend the last few decades of their life (and who they want to spend them with).

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Hi Jake,

My husband told me a while back that he wanted to post some mild photos of himself on Bluesky—shirtless, a little flirty, nothing too extreme. He’s always had a bit of an exhibitionist streak, and I’m no prude, so I’ve mostly found it endearing. I trust him, so it just felt like a harmless outlet. If anything, I’m kind of proud I have a sexy hus…

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Hi Jake,

I still can’t believe what just happened.

So, I dated a guy for a few weeks that I met on Hinge. I finally spent the night at his place, and we hooked up that night and again the next morning. I stayed most of the day and was getting ready to leave when he told me he’s HIV-positive.

I gave him a kiss and said I understood and that this changed not…

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Hi Jake,

All my friends think I’m a top, when I’m actually a bottom. And it’s not because that’s how I present, or that’s the type of energy I give off (although I do try to present as masc) — it’s because that’s what I tell them. So, yeah, I lie to everyone.

I actually haven’t even topped in a few years and am exclusively a bottom with hookups. I guess i…

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Growing up gay has been both one of the most liberating and challenging experiences I can imagine. On one hand, I’ve been able to carve out a life outside of heteronormative expectations and live more freely, gaining a deeper appreciation for authenticity, self-acceptance, and being fully seen. On the other hand, the reality of growing up in a world tha…

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