Tell Us About Your Worst School Age Breakup


Welcome back to Jezebel’s once-dormant, now revitalized Pissing Contest! Each week, we’ll pose a crucial question to you, the reader, in the hope that you will enlighten us with your own experiences in the comments. Then we’ll share those mutual mortifications (or whatever they may be) and keep it going until we know more about you than you know about you.

This week, school’s in session. Depending on where you live and your age, you’re probably making your way to class or wistfully walking by the new binders and shit at Target, wishing you had a reason to drop $40 on a new JoJo Siwa-branded sequined backpack. Whatever the case, we’re thinking about middle school and high school here at Jez, and reliving our worst breakups.

I’ll kick things off:

In 6th grade, after changing every discernible thing about my appearance, attitude and general interests, I managed to feign popularity. Not only that, but I actually became popular—so popular that when Scott asked me to accompany him to a nearby carnival where American radio rock band Hinder would play their only hit, “Lips Of An Angel,” I knew it was real and definitely not a prank. We spent the week leading up to the gig sitting close to enough to each other at lunch for me to score the daily Axe body spray contact high I so coveted. It was great, until he did not take me to see Hinder and I went on! my! own! anyway!, only to run into him there. He was hanging out with some skater boys from the high school. I was heartbroken.

Julianne Escobedo Shepherd won’t travel for no man:

In 11th grade, my best friend Marie and I were dating best friends named Dino and Jeff. When she and Dino broke up, I also broke up with Jeff because they both lived three hours away (we met AT CHURCH CAMP) and the commute was too much of a pain on my own. It would foreshadow my dating life in New York, where I would never travel cross-borough for a man!

Clover Hope invented ghosting:

I’m really tragic and did not have many middle or high school boyfriends—probably three? And one of them was a pen pal I met through AOL and never in person… lol. I’m a loser. If I recall, the way I broke up with them was just that we stopped talking.

Frida Garza had drama for days:

Sophomore year I had a friend named Daniel who had a girlfriend (this was my MO). We flirted, always, and one time we went to an Angels and Airwaves concert. It was very romantic until I tried to kiss him and he was like, “WOW, What about our FRIENDSHIP?” And then we didn’t speak for a while. Looking back maybe that was fucked up of me? But it was also fucked up of him to flirt with me?

Prachi Gupta fell for her opposite (in more ways than one):

I don’t have any “worst breakup” stories from middle school because I never had a boyfriend. The closest thing that counts, I guess, is that during my senior year I briefly dated a guy named Craig. Craig was everything I was not: white, hot in that Abercrombie model way (he used to work there, which I thought was just SO COOL), popular, tall, blonde, in college, and, years later I would learn, gay. My friend more or less set us up—one night, on our way to some garba at the Hindu Temple (very cool), he met up with us at the Dunkin’ Donuts and my friend blurted out, “So, Prachi doesn’t have a date to prom.” Outwardly, I was embarrassed, but inwardly, I was extremely happy that my friend was so shameless.
Anyway, Craig agreed to be my date, and then we started dating. I think we went out a few times, but mostly we just talked on the phone every night, and honestly I cannot remember if we ever decided we were in a relationship. He invited me to spend a week at the beach with him and his family, but my parents would never allow this and I wasn’t planning on telling them I was secretly dating someone, so at that point I knew things between us had to end. Alas, we never did more than hold hands and dance together at prom—but what a great prom it was. We lost touch soon after that—I think I stopped calling him back, which was cold, but I’m pretty sure he got over that just fine.

Hazel Cills blogged her breakup:

I never really had a Real Boyfriend in grade school but I did once break up with someone early on in college by putting Whitesnake’s “Here I Go Again” on my blog when I knew I wanted to break up with him. When he texted me asking if anything was wrong I said “nothing” and then broke up with him in person the next day.

Katie McDonough was a punk, he was nu-metal guy, can I make it any more obvious?:

I met Sean, the cousin of my across the street neighbor, at some kind of Catholic function—either a communion party or a baptism. I was 11 or 12, had just started listening to Rancid, and interpreted the Korn patch on his backpack as punk-adjacent. We “dated” for maybe two months, during which I pretended to smoke cigarettes but never actually had to because we mostly talked on the phone. We broke up because he lived an hour away and it was too hard to keep meeting at the mall that was the midpoint between us. It felt very Romeo and Juliet at the time.

So tell us—what was your worst middle school or high school breakup?

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