1. How do you tell the difference between a slow-burn connection and settling for something that’s just okay?
There’s no settling down without some settling for…. because no one gets everything they want where romantic partners are concerned. So, if you’ve chosen someone you aren’t entirely sure about… welcome to the world’s most crowded club. Only time will tell whether you settled for something “just okay” (or worse) or if there was a slow-burn connection smoldering under the ambiguity and doubt. Good luck.
2. I’m a trans woman. A few weeks ago, I was hanging out with friends and one of them, a gay man who is also a furry, told me that he thinks his furry identity should be granted the same level of legal and societal validation as my trans identity. My first thought was, I wasn’t aware we were getting any validation! But my second thought was to be offended at the comparison between my identity, in which I exist every second of every day, and his furry identity, which seems more like a kink. Was I right to be offended?
“The statement this furry made is absurd and none of my friends would ever say something like that,” said a furry gay friend who agreed — somewhat reluctantly — to take a look at your letter so long as I kept his name out of my mouth/column. “My immediate thought is what is the furry guy actually asking for? Legal recognition? Does he want his fursona name on his government ID? If he wants to make his fursona his real name, there’s nothing stopping him from doing that; he just needs to get a legal name change. That said, while it’s certainly far harder to exist day-to-day as a trans person than it is as a furry, I don’t think boiling down being a furry to a kink is right. For some it might be ‘just a kink,’ but for others it is very deeply felt.”
P.S. While things have definitely gotten worse for trans Americans under the Trump administration, majorities of Americans still support the rights of trans people. Trans Americans have even gotten some legal validation — from the fucking Supreme Court, no less, in a decision written by Neil Fucking Gorsuch. Just as trans people shouldn’t be erased (and can’t be erased), trans wins and the progress we’ve seen over the last two decades (current backslash notwithstanding) shouldn’t be erased either.
P.P.S. My gay furry friend was too polite to say it, so I’ll say it myself: your gay furry friend is an idiot.
3. I want to love myself more and have the confidence to not care about other people’s opinion of me. Any tips for an anxious weirdo to stop caring about how the world sees me?
You can take other people’s opinions into consideration — you can show a decent respect for the opinions of mankind, as someone or other once said — without being paralyzed by them. But if you find yourself obsessing to the point of emotional paralysis (that “anxious weirdo” place), a good therapist could help you strike a better balance between consideration (of others) and confidence (in your own self/choices).
4. I was fascinated to hear the story of the woman who traveled to Peru for an erotic massage. She expressed frustration at not finding local providers. I have been giving these massages like the one the caller described on your show for five years but just to friends and those I meet on the apps. Is there a way to monetize this service? Where to start?
I’ve heard good things about Tryst — I am not endorsing the platform (“home of the independent escort”) but someone jumps into the comment thread to talk up Tryst whenever the subject of sex work comes up. So, just passing that along. (You also might want to listen to my conversation with podcaster and “love coach” Shaun Gelanos on the Savage Lovecast. Gelanos, a straight man, successfully monetized the erotic massages he enjoyed providing to women when he lived in the SF Bay area, which we talked about on the show.)
5. I’m a 30-year-old cis woman who has only really ever been intimate with cis men. Lately I’ve been chatting a lot with a trans man who has had bottom surgery. I’m really looking forward to getting intimate with him, but since this is new territory for me, I want to do a little research beforehand. I plan to ask him about what he likes and what feels good for him when the time comes, but I’m wondering if you have any advice or know of any good resources out there (i.e. written by a trans masc person) so that I can better understand his anatomy because most of what I’m finding is written by doctors or people that aren’t trans masc.
“Whether you’re a trans person exploring T4T sex for the first time, a cis woman who has historically dated cis guys, or maybe a cis gay man who’s never hooked up with a transmasc person, having a new sexual experience can feel daunting without guidance,” Jo Valdes wrote in an essay for Them. Valdes, a writer and intimacy coordinator, solicited advice from trans masc people on best practices where having sex with them is concerned. Go read the whole thing.
6. I’m active in water sports during the summer — no, not that type of watersports, but the kind with surfboards and paddle boards and sand and things like that. After a few weeks, I noticed that the tip of my cock will get little red marks, small abrasion raspberries, from rubbing up against the board, and sometimes, I think because I stay in a wet bathing suit for a while. This is suboptimal because it makes it look like I’ve got an infection of some sort. Any advice on what to do here?
A foreskin might help — if you don’t have one of those, you could look into getting one. In the interim, a triathlete pal recommends slathering your cock and balls with Trislide, an anti-chafing lubricant, before pulling on your wetsuit.
7. I’m a young 65-year-old straight woman and my ten-year relationship with my (narcissistic) guy ended abruptly without a reason. Prior to the end of this relationship, this guy successfully isolated me from all of my old friends. Now I am on my own. Dating apps are a wasteland and my day job has me in bed by 11 PM, even on weekends, and night life doesn’t get started where I live until after midnight. What can I do?
Reach out to your old friends and throw yourself on their mercy: “I’m so sorry for disappearing on account of my shitty ex and I would love to apologize in person and reconnect — if you have the time — and I promise I won’t spend the whole time complaining to you about my shitty ex.”
8. Have you read The Great Believers? It made me think of you.
I have not — but it sounds amazing. Thanks for the recommendation, and I will add it to the pile on my nightstand.
9. Does having a threesome with two people who are siblings constitute incest?
Interesting question.
I’ve always said there’s nothing necessarily gay about two straight guys having a threesome with a woman… so long as neither is quietly hoping something gay happens. So, by the same logic, one could argue there isn’t anything necessarily incesty about two siblings having a threesome with a non-sibling… so long as neither sibling is quietly hoping that scene from season three of White Lotus happens. But just as MFM threesomes will always be haunted by the specter of homosexual desire, SNS (sib-nonsib-sib) threesomes will always be haunted by the specter of incest.
P.S. There was definitely something gay about the threesome I had with another man and a woman when I was a closeted teenager — it was me, I was the gay thing about it.
10. If you could fuck any guy in history — they’re all gay in this scenario — who’s catching a facial?
My top three: Bagoas (as brought to life by Mary Renault in The Persian Boy), Antinous (prior to his deification by Emperor Hadrian), and Leopold II (at the time he was painted by Pietro Leopoldo).
11. I’m a gay man. My boyfriend says all gay guys watch porn and I’m lying when I say I don’t. But I honestly don’t.
I curate and host the HUMP! Film Festival — tickets for the fall season are on sale now! — so I watch a ton of porn (mostly straight) when the HUMP! Jury meets in December to select the films that make it into the festival. But I’m an erotica and imagination guy otherwise, perhaps because I came of age before online porn became a thing. That said, men like us — gay or otherwise — who don’t watch porn are rare, and shame does lead some people to lie about their porn consumption, and the lie is always “I don’t” and never “I do.” So, your boyfriend’s skepticism is understandable.
P.S. Tickets are on sale now for the HUMP! 2026 fall tour — watch the trailer and get tickets to a screening near you here!
12. My wife wants to go to a sex club “just to watch.” Is that a thing?
Lots of people go to sex clubs just to watch. And while watchers sometimes frustrate doers, smart sex clubbers goers — goers and doers — know that most couples come “just to watch” the first few times. So, making a couple that’s just came to watch feel welcome on their first visit (being friendly and respectful, not pressuring them to do anything they’re not ready for) could pay dividends on that couple’s third or fourth visit.
13. My (straight) husband and I have been monogamous for ten years. His go-to fantasy when we’re fucking is always — always, always, always — me sleeping with other men. Do I keep treating this like dirty talk or does listening to this over and over and over again (and helping him spin his the fantasy out) mean I have a hall pass at this point?
Keep treating it like dirty talk if you’re not interested in actually sleeping with other men. If you are interested in sleeping with other men, initiate a conversation with your husband about this fantasy when you aren’t having sex. (“Is me sleeping with another man something you want to keep a fantasy or is it something you actually want to happen? Because I am down.”) If he gets mad because you’re actually thinking about doing the thing he’s been encouraging you to fantasize about doing for more than a decade… yeah, then he never gets to bring it up during sex ever again.
14. My new ex is running around telling all of our mutuals that I was “emotionally abusive” basically because I broke up with him. No one has said anything to me about it. What the fuck do I do?
At least one of your mutuals said something to you — I mean, you wouldn’t know your ex running around talking shit if one of your mutuals hadn’t told you about it, right? As for why your other mutuals haven’t said anything, my hunch is that they know it’s bullshit. If mutuals suddenly start cutting you out of their lives, you’ll have to raise the subject yourself. If they aren’t cutting you out of their lives — if your mutuals are refusing to take sides (or, even better, if they’re easing your ex out of their lives) — continue to maintain a dignified silence.
15. My controlling ex had a huge problem with me posting thirst traps while we were together — not allowing me to show off was just one of the many ways he didn’t allow me to be myself — but now that we’re exes he likes every single one my thirst traps. Why is he doing this? I would ask him, Dan, but we had a bad breakup, and we are not speaking. (We’re straight.)
Your ex could be enjoying your thirst traps again because he no longer regards you as his property… or your ex could be slamming his thumb down on the like button to remind you of his existence and his disapproval. My money is on the latter, and my advice is to block him. (I could tell.)
16. My BF and I are moving in and have been dating for two years. I’m certain we are moving towards marriage. How do we combine finances and expenses as we begin living together?
Asking me about finances is like asking Dave Ramsey about fist fucking — finances are not one of my areas of expertise, just as (I assume) fist fucking is not one of his.
17. Hey, Dan, love the podcast! My question is, how do I approach opening up my relationship with my husband of 13 years? Knowing he is more reserved and traditional than myself.
I recommend jumping in a time machine, setting the dial to 2013, and having a conversation with your husband about monogamy, non-monogamy, and openness before getting married.
18. I’ve been seeing someone for six months. How long before I can demand being called his girlfriend?
Be the change you wanna see in this douchebag: Introduce him to someone as your boyfriend. If he freaks out, you’re never gonna be his girlfriend. If he says, “Your boyfriend? Yes, I think so, probably,” marry that man.
19. My boyfriend and I have been together for a little over a year. Our sex life is fulfilling, and we communicate really well. Recently my boyfriend let me know that he doesn’t get enough stimulation to keep him hard when I bottom for him, and this is why penetrative sex — when he tops — doesn’t last long. He’s mostly a bottom but we do flip from time-to-time. Do you have any advice on how to increase sensation for my boyfriend when I am the bottom?
Obvious suggestion: experimenting with different positions and different angles of penetration might help. Also, make sure your boyfriend knows he’s allowed to pull out, stroke himself for a second, and then dive back in once he’s fully hard again. But there’s a chance it’s not about stimulation, angle, etc., but about topping. Your ass could be completely sensational, but if your boyfriend is strictly a bottom, it’s not going to do it for him.
20. My partner and I have been together for almost nine years. We’ve always had a good sex life, though it’s become less frequent since our daughter was born. I’ve long suspected he’s bisexual. I also recently found messages and nude photos exchanged with a trans woman, including plans to have sex. The secrecy hurts, but I don’t necessarily see his attraction to men as a deal breaker. I love him, we still have a good relationship and sex life, and I don’t want to break up our family. I’d be open to some form of ethical non-monogamy. The problem is that he refuses to discuss any of this with me. How can I support him — or even figure out what’s really going on — if he won’t talk about it?
Your man can refuse to talk with you about this… but he can’t stop you from talking at him about it. So, tell him what you’ve always suspected, and tell him what you found. Then tell him you’re fine with an open relationship, so long as it’s ethically open. (You can add “mutually open” to that statement if you want the same freedom.) But if he’s going to have sex with other men and with trans women while he’s having sex with you, he needs to get on PrEP to protect himself and you from HIV, get all the recommended vaccinations for gay and bi men, and stock up on doxy.
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