STRUGGLE SESSION: Parsing a Crush, Life-Changing Sex, Getting to No, and More!

...ing is cheating. She says she doesn’t want to have sex with him. She sounds like his best friend. And there’s no evidence she’s cheating him out of time he would otherwise be spending with his wife, or confidences he’s not (also) sharing with his wife. Sure, if she is flirting, if she is sending him hints that their relationship may become sexual, she should cut that out. And sure, she should seek available men to date, to distract her from that crush. But I don’t think we should be discouraging people from having friendships, even close friendships, outside of their marriages, with people who share a gender with the people we have sex with. From CHUMP’s letter: “Am I endangering his family just by talking to him so much, about absolutely everything (including sexual fantasies we will never act on), and treating each other as soulmates?” So, I’m reading too much into that parenthetical aside or BiDanFan is reading too little into it. But when my best friend shares sexual fantasies with me, we both understand he would like to act on them and will act on them when the right person comes along. The sexual fantasies CHUMP shares with her soulmate can’t be acted on because they can’t fuck each other (or haven’t fucked each other yet) because CHUMP’s soulmate is married to someone else and CHUMP doesn’t want to cheat. That doesn’t seem like BFF stuff to me. And then there’s this: “I don’t even want to be involved with him physically and we aren’t doing anything physical. We’ve both been good about maintaining that boundary.” Maybe I’m an outlier… but I don’t have to work at maintaining boundaries that disallow sexual contact with “friends” I don’t wanna fuck. And when someone tells me they’re hanging out with someone in a monogamous relationship but it’s okay because they’re “not cheating, at least not technically,” that means one thing: they wanna cheat with that person and they’re going to cheat with that person if they don’t stop hanging out with them. Hence my advice for CHUMP to go find herself a soulmate who is emotionally and sexually available to her. But I absolutely agree with BiDanFan on this: We shouldn’t discourage people from having friends — even close friends or entering into passionate friendships — with people who share a gender with the people they have sex with — as I discussed with Rhaina Cohen, author of The Other Significant Others, on this week’s Lovecast! Hal, a long time reader and first time commenter, asks… Is it possible that the guilt in this scenario comes from programming of a specific form of toxic monogamy that says your romantic/sexual partner also has to be your only emotional outlet? If CHUMP had no interest in fucking her married crush — please go re-read her letter — and felt bad about how close they were emotionally because that kind of closeness is for romantic/sexual partners only, that could definitely be evidence of toxic monogamy. But CHUMP feels bad because not because she’s confused about having powerful feelings for someone she doesn’t wanna fuck, but because she wants to fuck this guy and knows she’s gonna sooner or later. (And my money is on sooner.) Says Myk… Rhaina was a great guest and her book sounds super — one additional thing I liked was when she pushed back when you said, “Thank you for demeaning yourself by coming on my sex podcast” (something you often say to guests) by pointing out that you have meaningful, intelligent conversations on this podcast. Conversations about politics, about humanity, about relationships, and yes of course about sex but specifically in ways that do the OPPOSITE of demean! (Except in situations where the demeaning is desired and consensual)… I’m always glad when a guest says “what are you talking about?” when you jokingly throw your show under the bus. So, thanks for doing the show — YOUR VERY IMPORTANT SHOW ABOUT MORE THAN JUST SEX WHICH IS ALSO A VERY IMPORTANT TOPIC IN OUR SOCIETY AND WORLD — and thanks for having on guests like Rhaina who know how meaningful the show can be. I usually argue with people whose comments make Struggle Session, but this time I’m just gonna take my lumps… Says OrchidThief… The caller with the long-distance boyfriend didn’t say the sex was going to be “great.” She said it was going to be “life-changing.” I did not get the impression she expected great sex from this dude. And for a 34-year-old virgin, yeah, having sex for the first time is going to be life-changing. I get there are gender differences, but the difference between the way Dan handled this older virgin, compared to the female older virgin was pretty striking. The advice to ditch the virgin and find some other dude to fuck was pretty mean-spirited. To me, it sounded like the guy was nervous and insecure AF. Not some sleeper incel. People tend to use “great” and “life-changing” interchangeably — at least when they’re talking about sex. A cancer diagnoses, a layoff, a car accident, etc., qualify as life-changing events and are sometimes referred to as such, but when someone talks about a “life-changing” blowjob or a “life-changing” fisting session they usually mean a great blowjob or a great fisting session. So, it seemed clear — or seemed clear to me — that the caller was expecting the sex with this rather uncommunicative virgin to be mind-blowing, not catastrophic or even meh. And I encouraged her to go find someone else not because male virgins are pathetic — I’ve given pep talks to lots of male virgins over the years! — but because this particular male virgin wasn’t being polite, kind, or communicative. And, hey, the other person she finds could wind up being another one of those male virgins I’ve given pep talks to! Says XarXar… I thought Dan was harsh toward the 20-year-old man asking the 40-year-old woman if she wanted to do some BDSM with him. Yes, he sounds annoyingly persistent but it sounds like every time he contacted her she did the classic female (I do it too) “protect his feelings” thing and just said, “Okay, sure you can come along.” She seemingly never told him off or gave him any reason to think his advances were unwanted, despite saying she could tell immediately he had a crush on her. How was he to know she wasn’t entertaining the idea of getting with him? Dan perhaps has a point that the guy’s cousin could get a heads up that this guy will hit on her friends, so she can take that into consideration for the future. But definitely don’t out him as kinky, and I think calling him a creep is a bit far given we didn’t hear anything about her trying to tell him to calm TF down. Good call, XarXar. Men — even inexperienced and sheltered young men — need to understand that women deflect and learn to take, “I would love to, but I’m busy this Saturday and next Saturday and the Saturday after that,” for an answer… and that answer is “no.” But at the same time that we’re asking men to unlearn the toxic ways they’ve been socialized (to feel entitled to female attention), as Laura Kipness writes, we need to ask women to unlearn the ways the toxic ways they’ve been socialized (to defer to men). Women don’t always feel safe saying “no” to men — with good reason — but when a woman does feel safe saying “no,” she should deliver a clear, unambiguous “no.” Says High Estate about the same call… Not even sure it warrants a “heads up” to the friend TBH — he’s literally done nothing wrong! And it’s not clear that this is a general tendency — he might just find the caller and her approach to life less grating than I did and find her (specifically) attractive; it doesn’t mean he’ll hit on all women he meets. AuroraErratic disagrees… Hassling people after they say no is doing something wrong. Is it a hanging offense? No, but it’s not harmless either. “She didn’t say ‘no’ at any point for the past N months — I listened twice,” said High Estate in response to AuroraErratic. “She has done so now, post BDSM-proposition, and there’s no indication he has persisted since she’s done so.” So, the annoying 20-year-old kid took the “no” when he got the unambiguous “no.” Now, it’s not the caller’s fault that she lives in a world — we all do — where men sometimes murder women who say “no” to them and it took her a minute to get that “no” out. But it clearly worked — and seeing as the boy took it for an answer when it finally came, maybe it was unfair to call him a creep. One other thing about that call came in via email… Magnum Sub here with some feedback on Episode 908. I’m a long time listener who is also Jewish. I am really disappointed in the way that the caller who was asking for advice about the younger boy who wouldn’t leave her alone referred to the boy’s Jewish identity. She sounded incredibly ignorant when she said  he comes from a  “strict Jewish family” (many kinds of families can be strict, not sure why the Jewish piece is relevant) but I was willing to shake that off until she said, “I don’t think it’s appropriate for me to be taking a 20 year old young Jewish boy along to these events.” This sentence alone comes off accidentally anti-Semitic and I wish you had called that out. The issues that the caller addressed were about his inappropriate neediness, him not getting the picture she was not interested whatsoever, her connection to the family — made more challenging knowing how strict the family is, etc. — none of which had anything to do with his Jewish identity, except maybe the brand of conservatism that his particular household upholds. (Not to mention that many ‘20 year old Jewish boys’ might find themselves at kinky events.) I can’t imagine someone in a similar situation  stating, for instance, that the boy was from a “strict immigrant family” and she wasn’t going to take “a 20 years old immigrant boy” to a kinky event. I don’t think you had launch into a lecture on micro aggressions, but simply saying, “Being Jewish has nothing to do it with it so I recommend leaving that part out when you retell this,” would have sent the right message to me and other Jews, since the comment was awkward and hurtful — even if accidentally. I apologize if you were hurt by the caller’s reference to this boy — to this young (and persistent) man — being from a strict Jewish family. To my ears, it sounded no different than someone mentioning a suitor being from a “strict Christian family.” It seemed like an innocuous, matter-of-fact reference to this kid’s Jewishness to me; some kids are from Jewish families, and Jewish families — like Christian ones — run the gamut from very liberal to very conservative. And if an inexperienced young man with strict immigrant parents or conservative Muslim parents asked me to take him into a fetish party, I could imagine myself mentioning that fact to a friend — not to otherize the kid who wanted to go to the fetish party, but because the default assumptions people tend to make, e.g., that everyone you mention is Christian or was born here, are inaccurate and in their own way kind of problematic. I share this not to argue with you about how that played for you — and I’ll defer to you on it — but to share where I was coming from. Says KT Benjamin… Great answer to the caller who’s GF didn’t like him taking viagra. I’d add that they should both read the article at this link by Girl On the Net and add that you should have GOTN on the podcast to answer some questions with you. I’ve learned nearly as much from Girl On the Net’s blog as I have from you, Dan, she’s very insightful and would be a great compliment to your advice! We’ll reach out to Girl On the Net and invite her on the show! Thanks for the tip, KT! Says Aaron on Bluesky about Math Man… A struggle session comment: I’m SO glad that you didn’t take the bait from the guy complaining about straight dating app math by bringing a woman on to answer, as he had hoped. His request had a slightly victim-y vibe… and you emphasized his proactive potential steps. My followers on Facebook had some thoughts about that call. Says Monica… Consider what you have to offer women besides shallow entitlement. Most women don’t care if you’re pretty. Most women do care if you’re kind, funny, generous, thoughtful, and so on. Says Nancy… Maybe men need to expand their definition of “attractive,” just as they do for themselves. Men who treat women like human beings with multi-faceted, complex personalities don’t have to do this kind of math. And says Denis… This is so cringe. The only words that came to mind while listening to this guy’s call were “Stage 1 Incel.” Go to therapy, my dude, and get off the apps. You have some growing to do. Harsh! And speaking of dating apps, former Lovecast guest Magdalene Taylor had an opinion piece in the New York Times last week about the uselessness of dating apps (gift link).One of the things frustrating people about the apps: “[The] gender divide,” writes Taylor. “Women feel overwhelmed by messages, while men are underwhelmed by the lack thereof.” So, while it was dumb for Math Man to ask me to have some hot women on the show to give him pointers about catching the attention of  hot women on dating apps, he may have a point about how men and women experience the apps differently and maybe we’re being… too harsh? • Says SFMike64 about this week’s rant of a column… OMG. This nonsense about “micro-cheating” is going to make my fucking head explode. Anyone who thinks that’s a real thing deserves what they get. In Gay Land, unless your ex is toxic — and I have one of those — remaining friends with them is the norm, not the exception. Hell, one of my ex-boyfriends became friends with my MOTHER and she knew more about what was going on in his life than I did. She liked him because he was charming and a good guy, just not the good guy for me. (HT to my ex Brad and his husband John!) Says WTAF… The concept of “micro-cheating” involving confiding in a friend is setting people up for abuse. Abusers isolate the people they abuse, which prevents them from getting help. Having a friend or family member say “wait… they did what?” helps people recognize early warning signs, and having that person there when you need to get out is crucial when escaping an abusive relationship. More people need to join Dan’s one-man band here and shout from the rooftops that this is not ok. I made the same point about how this micro-cheating bullshit is aiding and abetting abusers in my last rant-of-a-column about this micro-cheating bullshit. Pushing this crap doesn’t just undermine good relationships, it’s normalizes and valorizes abusive behaviors. Okay, before we can close out this week’s Struggle Session… Our Muppet-Faced Man of the Week is Aaron Jackson, co-creator and co-star of DICKS: THE MUSICAL, a brain-melting work of staggering genius. (Don’t take my word for it — read the reviews!) Like the hottest Muppet-faced men, Jackson is 40% mouth and, after watching DICKS twice, I’m crushing so hard on him that Jackson should probably take a restraining order out against me now.