It Happened to Me: I Dated an Underage Guy

Why would I, a morally upright citizen, allow myself to have an underage boyfriend? The answer is, I don’t know.
Bree Davies
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Why would I, a morally upright citizen, allow myself to have an underage boyfriend? The answer is, I don’t know.


Have you ever made one of those "life plan" manifestos in that you share with your friends while you’re getting ready to go out or over brunch or something? You’re past the point of make-believe, but still not quite old enough to know what real decisions mean, and you’re philosophizing life’s place markers with no real reference to your actual existence at that moment.

When I was 19, mine went like this: Finish college by 21, get married at 25, have my first kid at 28, and my last at 32. Buy a house and get a job at a magazine were somewhere in there, too. 

The first problem with that life plan I made 12 years ago was that I didn’t even like my boyfriend at the time. Well, not enough to marry him. He was my first serious boyfriend, which was probably why he was a good candidate for my life plan.

But fast-forward a couple of years, and we had broken up. I was drinking way too much to have even gotten close to finishing college, and I was living in an apartment with a roommate. I had missed my first two goals already. But what would veer me so hard off of this life plan that I would never return to the track would this: I got a new boyfriend. And I met him on Myspace.

No big whoop, I suppose -- a lot of people were meeting on socially acceptable social networks. But my Myspace boyfriend was 17 and I was 23. Yeah. 17 and 23. My secret underage Myspace boyfriend was a complete stranger and for the record, his profile did not share his real age. Neither did mine, though (mine said I was younger), so the charade initially went both way

How could this happen? Why would I, a morally upright citizen, allow myself to have an underage boyfriend? The answer is, I don’t know. All of my boyfriends before him were “normal”; either my age or older. What I could not foresee was that this age gap trend would continue for the rest of my adult life. Literally, every single guy I met after this boyfriend has been five to ten years my junior. 

When we first started messaging each other, it was super fun. I wasn’t the most well-versed social networker; I didn’t utilize chat rooms or instant messenger much before this, so it seemed harmless. We weren’t actually going to meet each other. At least I didn’t think people who met on the Internet met real life. 

We moved onto texting each other, and from there he wanted to talk on the phone. I was not having it. By now, I had told my circle of friends about he and I talking, but I swore up and down that I wouldn’t meet him. Then he called me. 

I didn’t answer the first time.But he called me again, and I answered. And he had a really cute voice. I am easily swayed by attractive tones in a man’s voice, and his was deep and beautiful. We talked a lot. 

We play-threatened to meet each other for a few weeks, and of course, eventually, it happened. He came to one of my band’s shows and we hit it off. Like, hit it off like I have never hit it off with a dude before or since. Yes, he was 17 and lived with his parents. But after meeting him, it didn’t matter anymore. All of my friends already knew, and they seemed okay with it -- not without some serious "What in the fuck are you doing, Bree?” chiding, but still they were, for the most part, supportive. 

He was still in high school -- typing that out eight years after the fact makes me cringe -- but he had a job, was taking college classes, had already bought his own car and was preparing to move out when he turned 18 in a two months. He always picked me up for dates, took me out to dinner, paid for everything, and treated me like a princess. He had his shit together more than I did.

Most of the time, without the constraints of certain realities, he was a real boyfriend. (Except that one time, when he got a terrifying stomachache and ended up in the hospital with appendicitis, forcing me to meet his parents for the first time -- while he was being treated in the pediatric ward.)

For the nine-ish months we were together, things were cool and functioned better than any other relationship I had ever had. I stopped caring what other people thought about the age difference. He was a really good boyfriend. 

When we broke up, it was brutal. I was a full-blown drunk by then, and I put him through a living hell I think I am still paying my penance for. It took years, but we’re finally on friendly terms. It felt like he was more of the adult throughout our entire, still-evolving relationship. 

But after that it happened again. I met a dude at another one of my band’s shows, and he too was underage. I’m not saying “it happened” because I take no responsibility for my actions; I’m saying it because I truly don’t know how it happened. It was like I had unknowingly created a pattern for myself. 

He, too, was in high school, and he also had his shit together. This relationship, however, was very different from my previous one  -- or any other before. We didn’t date, we just hooked up. Now that he’s done with college, we still hook up.

For the last half-decade or so, he has poked his head back into my life once of twice a year. He takes me to dinner, regales me with his world travel stories and then we fuck.

He’s 22, but he’s motorcycled and bicycled up the West Coast, traveled all over Europe and South America alone, speaks Italian and Spanish fluently and works as a liaison between Spanish and Italian businessmen. He’s preparing for med school and volunteers at a hospice, for fuck’s sake. How could I not love him?

Since my underage MySpace boyfriend and my ongoing "Graduate"-style booty call relationship, I have yet to date someone my age or older. Again, it doesn’t feel intentional, but it has to be, right? I’m 31 now, and I haven’t dated much (if at all) over the last four years. A part of me wonders if I'm avoiding dating because I’m freaked out by the age of the men I'm attracted to. 

Am I the only woman like this? Does it make me a pervert? How can I flip a switch and start liking dudes my own age so I can get on with my life already?