Maintenance Haze

...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. Afterall, 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. So, 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. So, 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 So, 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 just in case: 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 anyone 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 occasionally engaged in 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 these flirtatious and I wouldn’t go looking for evidence of them either. 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 your girlfriend anymore. Zooming out for a second… Many people wanna believe that younger women who are interested in older men — which would include 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 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 in a pair of gray sweatpants), AMS, but it seems possible — at least to me — that you might’ve run into one. Or… Your drunk neighbor and/or that other 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-yet-again/off-yet-again ex-girlfriend. Just because you haven’t found someone else in four weeks doesn’t mean you won’t ever find anyone 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 — what you had with your ex sounds pretty amazing — but you let and 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 or the relationship 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. We’ve been friends since I was 19 and he was 22. 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, like that one college student you’ve mentioned on your show, 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 know a few gay couples that 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 know met sleazy, e.g., they swapped hole pics on Grindr by way of introduction, they were chained to the same rack in a 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 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) into committing to monogamy on principal before he’ll even consider dating them. So, 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 and unhappy as a result, and they 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 be seen as damaged or emotionally stunted. (For the record: I don’t think people who prefer to be single are damaged or emotionally stunted.) So, 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) insists 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 looking. Which means your friend’s insistence on monogamy isn’t an obstacle he faces, but a barricade he built. Got a problem? Everyone does! Submit a written question for “Savage Love” now! Or record your question for the next Lovecast here! Follow Dan on Instagram and Threads @DanSavage. Follow Dan on BlueSky @DanSavage. Discounted “early bird” tickets for HUMP! 2024 are on sale now! The best little porn short film festival returns to theaters in Seattle on February 8th before heading to San Francisco and Portland! And check out the full list of cities HUMP! 2024 is coming to next year! There’s nothing like seeing HUMP! in a theater! Order your tickets now and save!