Source: When I Was 13, My Boyfriend Was Obsessed With My Mom Publisher: Cartoons Hate Her | Author: Cartoons Hate Her Published: February 10, 2026 | Archived: March 21, 2026

First of all: yes, this story is true, at least the way I remember it. But keep in mind my real-life mom will be reading all your weird comments, so don’t be mean to her. I don’t blame her for this, and neither should you.

I could look cool when I wanted to!

Josh was a little geeky-looking himself—tall, skinny, short brown hair with the notorious 2000s-era gelled flip at the hairline. He wore glasses, polo shirts, and other AV-club coded attire. I was not instantly physically attracted to him, although at the time I would say I was too sexually immature to be capable of feeling that way about anyone. But either way, I liked Josh enough to go out with him. I loved the idea of having a boyfriend, holding hands, and going on dates. And after a few extremely awkward double dates, with Nadine as the mediator and interpreter of our mutual feelings, Josh became my boyfriend.

Because we were too young to drive and we lived in the suburbs, our moms were a pretty big part of our dates. Even before my mom met Josh, I warned her not to “do anything funny.” At the time, she probably saw this as her teenage daughter being irrationally mortified by everything she did, and she wouldn’t be wrong, as I had previously admonished her for yawning “embarrassingly.” But from my vantage point, I had a long history of friends and crushes practically preferring my mom to me, and I didn’t want that to happen with my first real boyfriend.

Unlike other moms, she wasn’t a disinterested chaperone or chauffeur. She might deny it, but the way I saw it, she tried pretty hard to be funny, charismatic, and make my friends like her in a way that felt completely unnecessary. She didn’t try to be “cool” like the infamous character Amy Poehler played in Mean Girls and she wasn’t a MILF in the typical sense (she was pretty, but in a very age-appropriate way, with no nipping and tucking, no revealing clothing, and no attempts to look twenty.) If anything, she leaned into being dorky and, in her words, “un-hip” in a way that unfortunately made her more appealing. Given her history of razzling and dazzling all my friends, I was terrified that Josh would like her just a little too much. And well, this fear was entirely warranted.

You may be wondering what on Earth my mom did to make my friends like her so much. Perhaps you are a forty-something-year-old mom yourself, and your own children and their friends consider you mondo-cringe, and you can’t imagine how my mom successfully won over a bunch of teenagers. Fair. The best way I can refer to this behavior is “comedy hour.”

To this day, if I go to a restaurant with my mom, she will engage in friendly, chummy banter with the wait staff that goes beyond politeness and frequently involves little jokes and one-liners. Although she’s now single, it’s never flirtatious, which almost makes it more absurd, because she has absolutely zero agenda outside if making strangers laugh. Most of the time, these people are women or an entire generation younger. Now that I’m not a perpetually-embarrassed teenager, I find this friendly, bubbly tendency endearing and wholesome. After all, wouldn’t life be better if everyone was comfortable palling around with strangers? We need more people doing comedy hour! The only times I find it annoying are when it derails the schedule of the day. For example, on a recent outing with me and my husband, my mom popped into a store to buy one thing she needed, and somehow spent over fifteen minutes at the register chatting up the saleswoman. She emerged from the store to declare that the saleswoman “wouldn’t let her leave” and wouldn’t stop talking to her despite her protestations that we were in a hurry. I’d believe her if clingy, needy salespeople weren’t apparently such a regular occurrence for her and only her. Another time, I heard my mom checking out at a store and I suspected she was extending the checkout process to do comedy hour. My suspicion was confirmed. As she signed the receipt, I could hear her telling some kind of story, saying, “And well, he turned out to be gay…”

As a young child, I sometimes enjoyed this quirk of hers. When my friends would come over for playdates and I would regale them with stories of fairies and invisible dragons living in my house, my mom would back me up and amplify the embellishments, providing much-needed adult credibility to my claims. My mom was “fun” in a way that other moms weren’t fun. But as I got older, I really did not want my mom to be central to social activities with my peers. Unlike many other teenagers, who find their moms insufferably cringe in all settings, I actually really enjoyed spending time with her, just the two of us. But I did not want her to be the “fun mom” when my friends were around. Her personality was just too big, and ran the risk of overshadowing mine. She was too charismatic, with too many interesting stories (she used to work in a very exciting industry, which all my friends found fascinating.) When my friends were around, I wanted my mom to be helpful but invisible. Not entirely fair to her, but you’re about to see why.

Okay, so back to Josh. I warned my mom not to do anything that could run the risk of making Josh like her more than he liked me. I told her to basically ignore him unless it was a matter of safety or logistics. She incredulously asked me why a fourteen-year-old boy would ever prefer the middle-aged mother of his girlfriend over his actual girlfriend, and informed me I was being silly, as if she had not overshadowed me with my friends so many times before.

While my mom did a decent job of making herself as boring as possible the first few times she met Josh, our relationship continued for longer than anyone expected. Typically, my “boyfriends” at this age lasted about two weeks until their friends found out they had a girlfriend (which, in middle school terms, is actually extremely gay) or until they realized having a girlfriend entailed calling and spending time with said girlfriend—the horror. But Josh was the first boy I dated who seemed to have matured sexually. That doesn’t mean he was “mature” in any real sense, but we did real teenage boyfriend-girlfriend things. Contrast this with my seventh-grade boyfriend who spent our one and only date reciting McDonald’s commercials at me while jumping on his parents’ ottoman. Josh and I made out. We went on dates. He was, arguably, far more interested in below-the-belt sexual activity than I was (I was interested in romance, and maybe kissing, but still found anything sex-adjacent to be kind of gross.)

I asked my mom if she was OK with me writing this and what she remembered about Josh. “Wanna get high” is still seared in her mind more than 20 years later.

Made worse was the fact that all of this happened around the time that the band Fountains of Wayne released their viral song, Stacy’s Mom, about a teenage boy who uses an age-appropriate girlfriend named Stacy as an excuse to get closer to her mother. Notably, the teenage boy character in the song was just as delusional as Josh was. At one point, he sings that he knows Stacy’s mom wants him because she says romantic things to him, like “You missed a spot over there” while he’s mowing her lawn. Josh also took any nugget of attention from my mom and rode with it. If she gave him an inch, he took a mile. In the middle of one of our millionth fights on the topic, my mom exploded, “You think I like him following me around like a dog? Guess what: I find him annoying as hell!”

You might be wondering why on Earth I still liked Josh. A girl with any degree of self-respect would have dumped a guy for having an obvious crush (even a platonic or parental crush) on her own mother. But I wasn’t like other girls—I was insane. None of the kids at school liked me, even as a friend. I was unpopular enough that I had projectiles thrown at me when I walked to class. Boys would prank each other by telling me that their friends had crushes on me—something too ridiculous to ever be taken seriously (I still don’t fully get why. I thought I was ugly at the time, but I was cute!) I thought Josh was the only boy who was ever going to like me.

I didn’t even really enjoy spending time with him. I never developed physical attraction for him, even though I hoped I would. I didn’t enjoy fooling around with him, and sometimes I made that clear, but I was too afraid of conflict to make a big deal out if it so often I just let it happen. This wasn’t healthy, but with no prior sexual experience, and without a literal gun to my head, I thought everything he did was normal. I hated the idea of disagreeing with Josh, even as he explicitly told me he wanted me to disagree with him more often so I wouldn’t be so boring. Looking back on this relationship as an adult woman, it makes no sense. The whole mom-crush aside, it was an objectively horrible experience. And yet, I wanted to stay. I cried over the idea of our courtship ending. I worried every week that Josh would break up with me, and performed elaborate shaman-adjacent rituals to prevent such a thing. One could argue my mom should have eventually forbidden us from seeing each other, given how miserable he made me, although she didn’t know the whole story. But I made it clear to her that our relationship ending would “ruin my life.” As ridiculous as it sounds, I wanted to marry him. Not because I liked him, but because I thought nobody else would ever want me.

As the school year ended and summer began, I went off to sleepaway camp. I was terrified at the idea of being away from Josh for a full three weeks, but my mom assured me that she would facilitate a visit in between the first and second three-week sessions of camp. This meant that she would drive Josh for a full three hours to come and visit me at camp for a day, then drive him home for another three hours. I’m sure Josh was absolutely thrilled about this experience. Although I wasn’t in the car, my mom has since told me what happened: lots of South Park impressions, to the point that she eventually dissociated and stopped hearing them. Also, he repeatedly tried to engage with her about ways to help me develop and mature. He suggested, once again, that I get a job. He complained about my lack of a backbone. At one point, probably mistaking my mom’s silence for agreement, he suggested the two of them team up to get me drunk so I would unwind and become more confident. At this point, my mom snapped back to reality and asked him, “Did you forget that you’re talking to your thirteen-year-old girlfriend’s mother?” Josh piped down momentarily, then resumed the conversation with a dazzling rendition of Mr. Hanky the Christmas Poo.

It feels worth mentioning that Josh didn’t even drink, and had no access to alcohol. Presumably, he thought my mom was “cool” enough that she would facilitate this. Obviously, that’s insane, although she had already agreed to spend six cumulative hours driving him around and listening to his Cartman impression, so at that point, he probably thought anything was possible.

After I finished my time at summer camp, Josh and I continued seeing each other. He even joined us for a week on our annual family vacation (in a separate bedroom of course—it had been a tradition for me to bring a friend on our summer vacations, to that wasn’t too unusual.) After the vacation, my mom understandably opted out of any kind of Josh-related chauffeuring and made my dad drive him another three hours back to his house. But that summer vacation spelled the end of our relationship. My paranoia went into overdrive as Josh was literally living in the same house as my mom, following her from room to room, showing up next to her as my mom closed the refrigerator like some kind of A24 jump scare. The more access he had to her, the worse it was. By the time the vacation was over, I had no interest in him anymore. The idea of him breaking up with me still made me sad, but his obsession with my mother had finally, fully, repulsed me. Even then, I couldn’t bring myself to end the relationship. We sleepwalked through our courtship for another two months, and finally he broke it off with a quick phone call. Surprisingly for me, I felt nothing but relief.

Josh and I went to separate schools. We didn’t really see each other again, although we briefly reconnected in our late teens on a date to The Cheesecake Factory with zero spark, and then went our separate ways permanently. Years went by, and I didn’t really think about him, although I’m sure my mom was still plagued with phantom Towelie impressions that only she could hear in the distance when she thought she was alone.

The only other time I came close to seeing him was about fifteen years after we originally met, when my mother informed me she was deep into a Facebook comments section on a news article and saw an aggressive young man arguing some “extreme position” (she has since forgotten what it was.) That man was, of course, Josh. I am only grateful to her that she didn’t make his day and shoot him over a like.