The Glorious Way You Broke Up With a Frenemy

Screenshot: The Office

Have you ever had a frenemy? A pal who is also your nemesis? More often than not, “frenemy” is a nonsense term utilized to pit women against one another (what isn’t at this point). But sometimes it’s an accurate way to describe a former friend who depleted your life force—someone who you once held near and dear but soon realized was toxic so you had to 86 their ass. I want to hear all about those breakups: How you got rid of your own Caroline Calloway, even if it took years.

I’ll begin: I once broke up with a frenemy by moving to another state. There are more painful details to that story, but Pissing Contest is all about you, dear reader. You have the floor. Tell me about your friendships gone awry.

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But first, let’s take a gander at last week’s winners: here are your silliest regrets.

itsnotaboutthepasta, you win, because I felt this in my damn bones:

This is the very dumbest regret ever, but: In the summer of 1998, I had just turned 12, newly full of hormones but very sheltered/naive, and was attending Vacation Bible School. An older boy (15? 16?) that I had a crush on (I had a crush on basically everyone) was volunteering as a VBS helper, and with one of his other friends was chasing me and one of my friends around the very large church, which I think was also a K-5 school. Lots of empty classrooms and nooks for hiding in.

So my friend and I got separated and I darted into an elevator, but the door didn’t close fast enough. He leaned across the entrance and smirked at me. My hormone-addled brain couldn’t decide between Scared and Turned On, but my fight-or-flight instincts kicked in and I jumped over him and ran.

I spent the remainder of my adolescence filled with regret, CONVINCED that I should have stayed in the elevator, should have decided for Turned On instead of Scared. Nevermind that objectively it’s clear he had exactly 0% interest in kissing an oily-haired, slightly chubby, awkward 12-year-old. I think I was more mad at my skittishness than anything else.

Beige Iridescent Lipstick, yikes:

In high school I was reading aloud in class and pronounced ‘Hyperbole’ as “Hyperbowl”. I still visibly cringe when I remember that moment.

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basilbowman, go back to the zoo. It’s never too late:

I was 8. We were volunteering at an event at the zoo. I had five bucks for lunch, and there was one of those trampoline bungee cord things that lets you jump a million miles high right next to our booth. Lunch cost four bucks, that thing cost five. I took home a dollar in change and a lifetime in regret.

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E=MC Hammmered, this is the kind of shit I’m looking for. Bravo:

Once I was sitting in an airport bar waiting for my flight and a German couple was sitting next to me. At one point, the lady sneezed and I said “bless you” instead of “gesundheit.” This happened a decade ago and I still think about it at least once a week.

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Hobocamp, you should regret nothing because this is a nice and fun story:

My husband and I went on a honeymoon cruise, and one night the entertainment was a Newlywed Game style audience participation show where they picked a newlywed couple from the audience, a couple that had been married the longest, and a couple in between to participate as contestants. We were the newlywed couple. In true Newlywed Game fashion, one of the questions was “What’s the craziest place you’ve had nookie?” For some reason, my husband said Chicago. Then they brought out the other half from backstage and my answer was “my backyard when we were dating.” The whole place roared with laughter, and the host asked if anyone caught us. I said no, but what I almost said was, “I had a big bush,” meaning shrubbery we hid behind. But then I realized how embarrassing that would have sounded. Not a week goes by where I don’t wish I would have said it.

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Damone’s Five-Point Plan, listen to your friend! I hope they’re still your friend?:

Not seeing Tool in 1992, before they made it big. I was wary of the band, since the guy who tried to get me to go had also tried to get me to see GG Allin.

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eatthecheesenicholson2, I regret... you... not ordering the pigeon. You should like a good time:

Honestly not sure if this is a regret or not. It’s my second year of college, while I was still in a dorm. I woke up from a night of pretty heavy drinking. When I opened my laptop, I found that I’d been attempting to order a carrier pigeon online, and the only reason I didn’t was that I was too drunk to enter my credit card number correctly. For the best, but part of me still thinks... what if?

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wearebarnacles regrets not going to bone town:

I am 34 now, and happily married.

But.

When I was 22, I worked at a gem of a wine shop. A sublimely gorgeous, Brazilian orthopedic surgeon (my type of gorgeous — like, he could model for REI) was returning home in 2 days and buying some parting bottles of wine for his colleagues. I made eyes at him, wild eyes. (Was I leering? Am I a perv?) He returned the eye contact. I wasn’t sure if I was allowed to ask him out. I think he wasn’t sure if he should ask me out, given I was at work. He came back the very next day to buy more wine. I still didn’t know what to do. (Now, at 34, I would have known what to do.) We stared plaintively at one another. Eventually, the purchase was concluded and all possible small talk was had, and he walked out that door yet still lives large in my imagination. Oh, REI-model-doctor who twice bought Champagne from me, I still regret not bedding you.

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Apparently a lot of you regret not going to bone town, OneArtPlease included:

I definitely have a not-bedding regret too!

I used to post on a music message board for years and would meet up sometimes with people from there, especially when they were travelling through the city i worked in (i commuted about 45 minutes away from a suburb). I was in a long term relationship (that in hindsight was going nowhere fast).

One guy who posted on the board - who was known throughout as the hottest guy there (judging from pics of course) mentioned he was travelling to Canada with two of his friends doing a big road trip through the US. He listed all the cities he was going to - one of which was mine and said to message him if they wanted to meet up. I did so (and was the only one from my city apparently) so him and his two buddies arranged to meet with me downtown have dinner have some drinks, go to a baseball game. My boyfriend was working the night shift so couldn’t come with - i told him the details, so he knew all about it and was cool with it.

So i met the 3 guys in a hotel lobby downtown. We were all in our late 20s and they were all firefighter paramedics from Texas. Well, the dude from the message board was as hot in real life as his pictures had been and his two work friends equally as hot - all in amazing shape (that being part of their job and all) - t had been raining hard earlier when i met them and the one guy’s white t shirt was soaked through, showing off his impressive chest. They had adorable southern drawls and were super nice, despite my protests on the contrary - they bought all my food, bought all my drinks, bought my ticket to the game - as a ‘thank you for my hospitality’. I look alright, and am a pretty modern woman i guess - but i did not expect these guys to be so charming and nice and generous- plus their looks...i was taken aback a bit.

Anyway, we hung out for the 3 days they were here ending with us having some drinks and just as it was getting a little fun-drunk at their hotel bar, it ended with me running to get the last train back to the suburbs, back to the apartment i shared with my boyfriend. They were amazed i would commute like that - they said something like, ‘No way would girls in Texas ever do that - they would make the guy commute” (?) and said they were impressed i was so down to earth.

The guy from the message board met his to-be-wife literally a week later on one of their stops back to the US.

I should’ve fucked all 3 of them that night - looking back if anyone would’ve been into it i think one or all of them would’ve been - i’m 40 now but i highly doubt i’ll ever get a chance to bang a bunch of hot, polite firefighters again.

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Cestrumnocturn1, this one really made me sad, for some reason:

About 15 years ago I used to go to the same restaurant for lunch. Wonderful food and beautiful desserts. I always passed on dessert.

They went out of business when the real estate bubble burst....and I never got a single one of their beautiful huge desserts.

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VeryDivisiveMikey, lol:

While visiting New York awhile back, I ended up talking to this cute girl in line for the bathroom at a bar in Crown Heights. Very briefly, for maybe a minute, but in that time she told me her plan was to move to Hawaii to become a doula. I said “Ah, cool” or something like that. When I came out of the bathroom, I looked for her to keep chatting some more. She had gone. No big deal, happens.

Half an hour later, it suddenly dawns on me that I should have replied, “A hula doula!” I was distraught.

This was several years ago. I still think about it a couple times a month.

Let’s hear about those friend breakups below. Hopefully the other person doesn’t read Jezebel. If they do, you’re screwed!

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About the author

Maria Sherman

Senior Writer, Jezebel