1. I’m a woman living with a supportive, caring man. We’ve been together — on and off — for twenty years. The sex is always hot when we get back together. Then, after a year, the sex fades to nothingness. I believe the problem is that hot “reunited” sex only turns me on for a while and then I crave a more passionate, erotic connection, which is not his thing. He’s a wham-bam kind of guy. This time around, after we didn’t have sex for a year, he had an affair. I was devastated. Help?
Break up with him for cheating on you, get back together when (or if) you can forgive him for cheating on you, dump him when the sex has started to fade but before he has a chance to cheat on you again. Then start the cycle over again.
2. Will hooking up and having fun while single lessen my hunger for an LTR? I’m horny!
I met my husband doing something fun and sleazy (drunken one-night stand in Seattle) and I met my boyfriend doing something fun and sleazy with my husband (sex dungeon in Berlin). So, if you go into your hookups with the right mindset — fun hookup partners can make a great life partners — you could wind up finding the LTR you want while you’re out there having the horny fun you need.
3. Should I take on a summer lover even though I really want a partner?
Yes!
P.S. Lover? We’re not using that word — it’s gross.
4. I got on a dating app and pretty much instantly matched with the couples counselor I saw with my ex. This feels unethical. But is it?
It’s not unethical for a couples counselor to be on dating apps and — according to the American Psychological Association — it’s not unethical for a mental health provider to date a former client provided more than two years have elapsed since the client/provider relationship was terminated. (There are, of course, other considerations.)
P.S. I’m assuming this person “swiped right” on you and that weirded you out. If your pictures aren’t recent and/or aren’t representative, there’s a chance your former counselor didn’t recognize you. There’s also a chance your former counselor is a creep. You aren’t required to see this person just because you matched with them on an app. If it’s giving you the icks, block ‘em and move on.
5. What’s the most creative way you’ve ever heard of someone ending a relationship honestly?
I’ve watched some extremely dramatic breakup videos — people confronting cheating partners with evidence of an affair, sometimes at the altar in front of family and friends — but those breakups strike me as performative, vindictive, and (perhaps) deeply satisfying, but not “creative.” I’m not even sure what a “creative” breakup would look like or why someone would want to get creative with a breakup. Seems to me that breakups should be simple and direct conversations, not elaborately staged affairs. The flashmob proposal fad was bad enough — do we want to live in a world with flashmob breakups?
6. Thinking about staging an old-school flashmob wedding proposal. Good idea or not? Is there a reason people don’t seem to do them anymore?
“Do it,” said a good friend who staged a flashmob wedding proposal that went viral a decade and a half ago. “The worst that could happen is your partner says no and you’re humiliated in front of a bunch of people. The second worst is they say yes and then leave you for someone else after you’re married — you’ll still be humiliated, but in front of fewer people.” (Full disclosure: My friend’s partner said yes, married him, and then left him for someone else. Still, he has no regrets — not about his marriage or about the flashmob proposal he organized.)
7. What do gay men think of shirt-cocking? Women of all orientations seem to be united in our disgust of the practice, but are there any gay men who think it’s hot? I’m all for shirtless and naked men, but shirt-cocking is just…well, gross, in my estimation.
I have something of an in-house expert when it comes to shirt-cocking, aka “Donald Ducking,” which is when a man wears a t-shirt and nothing else.
“I love it,” said Terry Miller, my husband and a huge fan of shirt-cocking. “Maybe it was an old locker room moment that imprinted on me. But there’s something about a hot guy in a cropped tee and a Speedo or naked from the waist down. Fucking hottest thing ever.”
My husband, of course, speaks for all gay men everywhere.
8. What are your thoughts on the film Thanks for Sharing?
Do you mean the 2012 romantic comedy about sex addicts starring Mark Ruffalo and Gwyneth Paltrow? Haven’t gotten around to watching it but plan to — no spoilers, please!
9. Navigating the kink scene online as a professional (educator)… is it possible? Is it silly to share pics?
Thomas Rosengren was one of eleven finalists for the Teacher of the Year Award in Minnesota when a rightwing “news” website found some PG-13 pics of him in leather and posted them. Rosengren is longer employed by the public school where he worked. This didn’t happen in 1996 — it happened in 2026. So, while it’s definitely possible to navigate the kink scene as a professional educator, you’ll need to be very careful about where you post your pics and who you share them with.
10. I’ve never heard you talk about my kink: hotpast. Some people get turned on by listening to their partners talk about the sex life they had before they met. Like most men, I started out jealous if my girlfriend mentioned anything about her past. But as our relationship progressed — my girlfriend is now my wife — it became a turn on for me. I know I’m not alone. It’s hotwifing light!
I shared your letter with Hopeful Cuck, one of the hosts of the “Cuck My Life” podcast, because sharing stories about previous sexual experiences is sometimes a gateway to cuckolding. So, If this is a kink, I figured Hopeful and his crew would know about it.
“I dropped this question into the hive mind,” said Hopeful. “’Complimentary Compersion,’ and ‘retrocompersion’ got tossed out as other possible names for this kink, but we all agreed that ‘hotpast’ is the best name for it. For some men, this might be a stand-in for ‘actual’ cuckolding. So many men can’t imagine their wives sleeping with someone new but get turned on by the idea that she used to sleep with new guys. It’s also a much safer option for women. Is it a gateway? Probably not for all, but it can be a first step for some! We love the name!”
The Cuck My Life podcast — the podcast by cucks for cucks (and other adjacent people) — is available on all podcasting platforms.
11. Is it normal for my orgasms to get stronger the older I get?
It’s normal for you, you lucky bastard.
Read the rest of this week’s column here! And this week on the Lovecast: A woman who really wants a long term partner has gotten a “tantric opportunity” she may not be able to refuse. Hours and hours of hot sex? But the dude isn’t boyfriend material. Should take this once in a lifetime opportunity anyway?
A woman’s friend only dates women much younger than himself. He insists he’s being respectful and mindful of power imbalance. But it still gives her the creeps- should it?
On the Magnum, a man asks if hypnotism as a means to control someone sexually is a bunch of nonsense. Dan brings on science journalist Sadie Dingfelder to look into the matter. LISTEN HERE!
