Savage Love: Dec. 7, 2023

A tale of two shitty men

Dan Savage

It’s been a month since my great five-year-long relationship ended, and it’s my fault. We were both in our mid-forties, got along and had amazing sex three to four times a week. Yet I felt unsatisfied with the sex as it was almost always “maintenance sex,” at least on my ex-partner’s side. While I found it enjoyable, I knew she often didn’t. Another reason for my dissatisfaction was her inability to converse about the things I am most passionate about: music, movies, anime and the paranormal. Her interests were tax codes, insurance rates and other administrative topics. It should also be noted that my ex was a heavy pot smoker due to terrible menstrual cramps and, as a consequence, I became a huge pothead.

I actually broke up with her after our first year, but we ended up getting back together after she texted to tell me how heartbroken she was. I loved her and felt terrible about the whole situation, so I caved. I enjoyed my time with her and, despite conversations that were often boring, the pot-fueled maintenance sex was amazing, and the cuddling afterward was nice.

Fast forward three years, and an attractive woman in her twenties moves in next door and we quickly become friends. She would bring pastries over for my child (I’m a single dad) and once brought soup over when I had the flu. On one occasion, she drunkenly knocked on my door late at night wanting to hang out. I couldn’t, as I had my child at the time. Due to the dissatisfaction I had long felt about the maintenance sex that characterized my relationship, I was tempted to have sex with my neighbor if she was interested. I told my girlfriend about the late-night incident, and she demanded that I no longer hang out with my neighbor. I agreed, but soon I was hanging out with my neighbor behind my girlfriend’s back. My girlfriend found out by snooping through my phone and broke up with me. I was devastated and begged for her to forgive me, which she did on the condition that I cease all contact with my young neighbor. I agreed and another (pleasant) year passed until I met another young woman who seemed to like me.

This young woman, also in her twenties, was interested in all the same things I am. Knowing I couldn’t trust myself, I made the difficult decision to break up with my girlfriend. When she left my house for what I thought would be the last time, I felt like I had destroyed a functional relationship. It wasn’t perfect — lack of common interests, uneven sex drives — but we enjoyed each other’s company. A week later, I asked her to take me back again. She agreed. A few weeks later, I was again scheming to hang out with this twenty-something young woman. I was almost immediately busted by my girlfriend — she snooped and read my texts (this time on my laptop) — and upon discovering my betrayal, she screamed at me at the top of her lungs before slamming the door and exiting my life, this time, I fear, forever.

Will the regret and shame I feel ever go away? I’m utterly “maiden-less” now and, in my mid 40’s, am having a difficult time finding someone in my wheelhouse. I was kidding myself that two cute women in their twenties would be interested in a man like me. Not only did I wreck a perfectly good relationship, in the end I wrecked it for nothing. There was no pussy at the end of this shit rainbow. Please, Dan, tell me something that will make me feel better about this flaming dumpster. Will I find my way? Or am I condemned to forever lay in the bed I shat?

Anonymous Magnum Subscriber

You didn’t actually cheat on your ex-girlfriend, right?

You thought about cheating on her, AMS, and you were tempted to cheat on her, and you’d gone to the trouble of crafting a rationalization: the sex with the girlfriend, while amazing, was maintenance sex (at least on her end), which somehow ruined the sex for you without making it any less amazing. I’m not sure how one squares that circle — lousy and amazing — but in the end, AMS, you never actually touched someone else with your dick.

And it’s not like you were indiscreet. Your ex only learned you were talking to a young neighbor that — let’s be honest — nothing was likely to happen with because 1. You told your ex about her and 2. Your ex took that admission as a justification to snoop on your devices.

I’m not your ex-girlfriend — my boundaries are not her boundaries — but if I were a straight woman in my forties with a straight male partner in his forties, I wouldn’t be surprised to learn he’d engaged in harmless, delusional and discreet flirtations with other women. If I knew I couldn’t handle it emotionally, I would ask him not to tell me about his flirtatious interactions with other women and I wouldn’t go looking for evidence of them. So long as my boyfriend didn’t do anything stupid — so long as flirtations remained flirtations and didn’t turn into affairs and/or the kind of obsessions that result in neglect — I would suspend my disbelief, turn a blind eye, and enjoy a few harmless flirtations of my own. But, again, I’m not your girlfriend, AMS, and neither is girlfriend anymore.

Zooming out for a second…

Many people want to believe that younger women who are interested in older men — which includes a subset of young women who are specifically attracted to partnered older men for reasons —are a figment of the straight male imagination. That’s not true. While there are fewer younger women out there who are interested in older men than there are older men like to imagine and/or write screenplays about, some younger women are attracted to older men. (Jon Hamm is in his fifties and he can still get it.) The odds that you ran into two of these women in such a short period of time are close to zero (as are the odds that you look like Jon Hamm), AMS, but it seems possible — at least to me — that you might’ve run into one.


Your young drunk neighbor and/or that other young woman who was interested in the paranormal might not have been flirting with you at all and you misread — due to dickful thinking —simple/messy neighborliness and/or shared interests as sexual interest. 

I’ve been going on for a while here without answering your question: Will you find your way? Yes, AMS, you will. It’s only been a month since you broke up with your on-again, off-again, on-again, off-again, on-again, off-again ex-girlfriend. Just because you haven’t found someone else in four weeks doesn’t mean you won’t find someone else. My hunch is that you’ll wind up getting back together with your ex-girlfriend — on-again, off-again relationships are like that — and when you do, AMS, I hope you’ll have a renewed appreciation for her. Frankly, AMS, your ex-girlfriend sounds pretty amazing, and you sound like you let and your ego, vanity and self-pity fuck up a good-to-great relationship. 

If you’re lucky enough to have ex come back into your life, resolve not to take her for granted anymore. If maintenance sex makes you sad, only have sex when she’s horny — sex that she’s just as excited to have — and take care of yourself the rest of the time. If she doesn’t enjoy discussing music, movies, anime, and the paranormal, talk about other things (there are other things). And speaking as someone who doesn’t understand tax codes and insurance rates, being with someone who does — God bless you, Terry — is a pretty good deal.

P.S. They say there’s no fatal dose of pot, but if discussing the paranormal was something my partner insisted on, I would find it.

P.P.S. Delete “shit rainbow” from your vocabulary immediately.

P.P.P.S. Thank you for being a Magnum Sub, AMS!

My friend needs help. He’s an adorable 30-year-old gay boy who’s a top, but his mannerisms, height, demeanor and exceptionally cute butt suggest otherwise. 

Here’s the issue: He’s so strident about monogamy that it turns most men off, which is a shame. Most gay/bi men expect some degree of openness. Additionally, he thinks relationships that start out as hookups or something slightly sleazier are suspect, whereas I and the most significant men in my life disagree. 

Besides occasionally offering a nudge, is there anything I can do for him? He truly is a catch, and I don’t like seeing him glum. He’s broken up with several guys who can’t commit to total monogamy forever — all while still being flirty with me, a guy who has multiple partners. (Nothing would work out between us, as we’re both tops.) 

I know that my life is enhanced dramatically by my boyfriends, and I just want him to have what I have, instead of going to bed alone almost every night. How can I help him?

— Boy Explaining One Possible Erotic Niche

Does he want to be helped, BEOPEN?

I’ve known some gay couples who met cute, e.g., their straight besties conspired to introduce them, they reached for the same sweater on a sale rack, they took a class together at college, etc. But most gay couples I’ve known met sleazy, e.g., they swapped hole pics on Grindr by way of introduction, they were chained to the same rack in a sex dungeon in Berlin, they met sucking dick in a cruisy toilet at college, etc. I’m going to guess that your friend, having been out and for at least a decade, has met enough gay couples to know that ruling out guys he meets under sleazy circumstances — he doesn’t go to bed alone every night — is an act of romantic self-sabotage. Same goes for browbeating men who might be willing to consider monogamy (at least at the start, at least for him) by insisting their commitment to monogamy on principle before he’ll consider dating them.

I’m guessing this problem — your hot friend’s inability to find a boyfriend — isn’t a problem for him. Some people set unrealistic expectations/conditions at the start of their dating lives, they’re alone as a result, and they eventually adjust their expectations/conditions. But not everyone who sets unrealistic expectations/conditions is unhappy about being alone — some prefer to be alone — but they would rather be seen as pitiable than seen as being damaged or emotionally stunted. (For the record: I don’t think people who prefer to be single are damaged or emotionally stunted.) They never adjust their expectations/conditions because they’re only pretending to be unhappy about still being single.

Seeing as there are guys out there who want monogamy as badly as your friend (my hunch) on pretending he does, BEOPEN, the fact that he hasn’t managed to locate even one over the last decade is solid evidence he isn’t seriously looking. Which means your friend’s insistence on monogamy isn’t an obstacle he faces, but rather a barricade he built.

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