"Hi Jake,
I’m a 75-year-old lesbian and have never written to an advice column before. But last week, something happened that I’m struggling to wrap my head around.
I went to my Pride planning committee meeting and had a really awful experience with a younger man who disagreed with me about something. The man was probably in his late 20s or early 30s. As we were talking, he rolling his eyes and butting in to call me “out of touch” and “silly” in front of the entire room.
I tried to defend my points, but he kept talking over me like nothing I had to say mattered. The whole thing felt incredibly dismissive, made even more painful by the fact that nobody else stepped in or stood up for me. It felt like they all agreed with him.
I was honestly upset for a day or two afterwards. The more I thought about it, the more it bothered me. I still can’t shake the feeling that he saw me as some old relic with gray hair and outdated ideas instead of an equal and valuable member of the committee.
This young man has no idea that I spent much of the 1980s helping take care of dying young much like him when much of the world ignored them. I sat beside hospital beds, brought groceries to friends in need, marched in the streets, went to funerals, and watched an entire generation–my generation–disappear.
Back then, I showed up because people needed help, and because that’s what being a queer community meant. It was unsettling to feel dismissed by someone benefiting from freedoms people my age fought so hard for him to have.
Am I wrong for still feeling hurt by this? And should I have said something in the moment?
Still Here, Still Queer
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He turned 50 having never been in a serious relationship.
Not for lack of trying. Just — life went differently than he planned.
This week’s Ask Jake is about reaching a milestone and feeling like you missed something. The quiet grief of a path that didn’t go the way you imagined. What our unconcious resistance to love actually costs us. And why it might not be too late.
Jake also opens up about something personal: his husband Jamie, who turned 50 thinking love had passed him by entirely — and what happened on a trip to Maui that changed everything.
This one is for anyone who has ever wondered if their shot already came and went.
— — —
The full column, including Jake’s unfiltered take, is available to paid subscribers.
Paid members get two deep dives a month, the complete version of every column, and at the Founding level, a personal written response from Jake to your own question.
Subscribe at the link in bio.
#AskJake #LGBTQTherapy #QueerMentalHealth #GayTherapist #SingleLife
"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 husband.
That said, the last time I saw his profile, it was just a few suggestive gym progress pics. Now I’ve found out he’s been building a much more explicit presence than I realized, and it’s starting to blow up. He has a big following now, and people we actually know are beginning to recognize him. That’s how I even found out how far it had gone.
So now I’m caught off guard. What I thought I was agreeing to feels very different from where we are now. I mean, it’s not just suggestive anymore… it’s gone full-on sexual.
Part of me thinks I shouldn’t care. We’ve always been open, and I don’t want to come off controlling. But another part of me feels betrayed and hurt that this escalated without really including me.
How do I figure out what my boundaries actually are here, and how do I tell him I might not be okay with this anymore?
Didn’t See It Coming"
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"Hi Jake,
I think I’m addicted to cruising… but it’s not even for the hookup. What’s exciting to me is the eye contact, the silent back-and-forth, the head nod that feels like a win. It’s about the chase more than actually doing anything. It’s especially fun when it’s not even a gay spot. I’m on Sniffies pretty much everywhere I go. A Home Depot bathroom, a Macy’s dressing room, a Chase Bank parking lot, even a random truck stop on the side of a highway during a road trip. It’s almost like I can’t help but check who might be around.
Sure, part of the thrill is that some of these guys might be bi or even straight-curious. If that’s the case, it feels like even more like I’ve hit the jackpot, and getting something I’m not “supposed to.” But the weird part is, the second it feels like it could actually happen, I’m out. I lose interest and move on to the next. And then I’m right back looking again, like I need another hit. So what am I actually chasing… and why does it never feel like enough?
No Cruise Control"
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"Hi Jake,
My boyfriend and I have been together a few years, and early on we agreed to split everything evenly—rent, bills, trips, all of it. We liked keeping things simple and fair, without any weird power dynamics. It felt very “us,” and it’s always been nice to feel like equals.
So that’s what we’ve been doing… or so I thought.
The other day, we were going over our monthly expenses like we normally do, and I saw a deposit on his screen that caught my attention. It was way higher than anything I’d seen before. I pointed it out and he tried to brush it off at first, but then admitted he actually makes a lot more at his job than I thought, and said has been putting the extra money into a separate account I didn’t even know about.
He said it was just “extra savings,” and no big deal. But the more I think about it, it’s not sitting right with me. It’s not like I want access to more money; it’s that we built our whole 50/50 setup on numbers that weren’t real.
Now I’m spiraling a bit. Is he building a safety net for himself if we break up… or quietly helping out some twink I don’t know about? He does have a bit of a “savior” streak with certain friends.
I don’t have proof of anything, but the secrecy is getting to me. If everything’s above board, why not just be upfront? Part of me thinks I’m overreacting, since in theory we’re still splitting everything 50/50. But another part feels like this says something bigger about honesty—and how he sees our relationship.
Is this something I should actually be concerned about?
Doing the Math"
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"Hi Jake,
So, my husband sent me the Queerty article this week about Kristi Noem’s husband allegedly being into “bimbofication,” and he was going off about it. He started ranting about how gross and “pathetic” it was, and said something along the lines of, “Imagine being turned on by that?!”
I laughed along in the moment… but the problem is: I didn’t totally feel like I was laughing.
While I’ve never used that exact term—and I don’t agree with politicians (or their spouses) who act against things they secretly do—I’ve had my own version of this in my head for years. Not a full transformation fantasy or anything extreme, just a fascination with exaggerated, hyper-pretty, slightly clueless “himbo” energy. Think overly-groomed, smooth, a bit airheaded, and more focused on perfect pecs and biceps than having much going on upstairs.
for a minute… less in control, more… objectified. Which is not how I move through the world at all.
I’ve never told him this or acted on it. It’s just this quiet fantasy of mine. But after hearing how strongly he reacted, I feel like I’ve gotten a glimpse of exactly how he’d see me if I ever shared this part of myself.
I feel stuck. Do I keep this in my own private “spank bank,” or do I find a way to share it with my husband and risk being seen as “gross” or “ridiculous” by the person I’m supposed to feel safest with?
Himbo in Hiding"
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"Hi Jake,
One of my coworkers is constantly in my DMs on our work Slack with really explicit, slutty talk. It’s not necessarily about hooking up with me, but more like running commentary—stories about jerking off, getting turned on at work, asking what I “did” with my boyfriend the night before, stories about his brief foray into being a “nudist.”
At first, I’ll admit, it was kind of entertaining, so I engaged. But over time, it’s gotten more X-rated, and now it feels like it might be crossing a line. I’m finding myself uncomfortable—I literally minimize our conversation anytime someone walks behind my desk.
What makes it confusing is that this kind of talk can feel pretty normal among gay guys. So I’m struggling to tell if he’s actually doing something inappropriate, or if this is just typical horny gay banter and I’m overthinking it.
Do I need to say something—or even report it? I’d feel bad getting him in trouble, especially since I didn’t shut it down sooner (and honestly, if anyone actually read our conversations, I’d be mortified).
So at what point does this become an HR issue versus “this is just how gay men talk”? Does he get a pass because he’s waving a rainbow flag? I’m pretty sure a straight guy couldn’t get away with talking to a female coworker like this.
Too Much Slack"
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"Hi Jake,
I had a close male friend who is openly gay (I am non-binary, assigned female at birth). We had a lot in common, became close really quickly, and started spending a lot of time together. Slowly, I realized I was falling for him, and one evening after a party, I confessed.
On the spot, he took it really well. He said his feelings are entirely platonic and that he likes me as a person. I felt a sting, but I was also relieved that I’d told him and didn’t have to keep it a secret anymore.
A few days later, he messaged me saying he wants to take a break from our friendship and needs some space. I apologized and agreed to it. Suddenly, not having my friend around broke my heart. I spiraled into self-blame and felt guilty for ruining our friendship. I haven’t heard from him since.
I keep wondering if I crossed a line without realizing it. As someone who is non-binary, is it somehow wrong or inappropriate to have a crush on a gay man? I wasn’t trying to change him or expect anything. I just developed feelings.
Is this about identity and incompatibility? Or is it simply that he didn’t feel the same way and needed distance? I don’t know if this is just what happens when feelings aren’t returned.
Now I’m at a loss. Should I reach out again, or let it go?
Out of His Binary"
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"Hi Jake,
This guy from my old gay kickball league texted me out of the blue and started flirting. It felt harmless, so I went along with it, but pretty quickly he started hinting at some kinks. He said he liked when guys were mean to him and called him names — and then it got even weirder.
Before I knew it, he was asking me to demand that he send me money. I was confused at first, but he explained that being dominated and “forced” to pay is his thing. I thought it was kind of funny, so one day I texted, “Listen, you little pig — Venmo me $300 right now so I can buy new shoes.”
Sure enough, minutes later, the payment showed up.
This has been going on for a few months. I’ve “ordered” him to send money four or five times now, and he’s sent me around $3,200 total. The meaner and more degrading I am, the better — so once I even told him I needed money to buy my new, sexy boyfriend a phone, and he said that was the hottest demand yet (I don’t even have a boyfriend).
My friend told me this is really uncool and that I should stop taking his money, but I don’t really see why. He likes doing it, and he has other guys he does this with, so it’s not like it would stop if I quit. So… can I keep taking his money for basically nothing? Is there actually any harm if this is what he wants?
Venmo Dom"
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"Hi Jake,
I keep seeking out sex even when I’m not really feeling it. It’s almost just like a habit or something. Even when I’m not horny, I still open the apps, scroll, message, or even meet someone, just… because. Honestly, I don’t even know why I’m doing it.
Sometimes, when I finally do hook up, nothing happens — I can’t even get it up. I guess I wasn’t in the mood, even though I thought I was. The lead-up always ends up being more exciting than the reality.
All I know is that I’m wasting time and emotional energy seeking guys out, acting “as if” I’m all horned up, then either flaking or going through with it only to disappoint them or myself. I mean, who wants someone to come over after a long buildup only to end up unable to perform?
It’s confusing and a little embarrassing. Why am I constantly doing this?
Lost in the Chase"
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