My Six Worst Relationships and How They Failed

Categories: Serrano Time

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flickr.com/suzijane
Not me and not someone I dated, but it may as well have been
Editor's Note: Shea Serrano is an award-winning music writer and goofball who recent exploits include Bun B's Rapper Coloring and Activity Book. In his new column, he writes about his life and times.

I went running the other morning. I used to run all the time. I was in shape, and had a six-pack for a week. I then threw all of my shirts in the trash, which was not that smart.

Alas, now I'm sloppy and unhealthy. The buttons on my pants are always angry. So that's why I went running, and while I was doing so, Dustin-Prestige's album Dharma cycled on. The tape, which is very good, focuses on the dissolution of a relationship. It also got me thinking about about some of my own relationships that have withered away. So here they are: Six failed relationships.*

*Now, to be clear, I use the phrase "relationship" extremely loosely. Before I got married, there was a seven year period where I asked nearly every girl I saw to be my girlfriend. (If I asked 100 girls to show me their boobs, they couldn't ALL say no, was how I felt.)

Girl: Adrianna
My Age: 12

Adrianna was the first girl I kissed. She wasn't very pretty but she was really good at basketball, which was more important to me back then. ("I don't care that she's got a cloudy eye, bro. She's fucking devastating in the pick and roll.") Also: She didn't scrunch her face up like she was staring at the sun when she looked at me. That's how I knew it was love.

See also: Here Are the Songs They Play at a Middle School Dance

Ours was a relationship of convenience. She was spending the night with a friend who lived next to my uncle, and I was spending the night at my uncle's. So I snuck over at night and stood at the window of the bedroom they were in, staring like a total weirdo. (It was not nearly as romantic as it sounds. There were definitely a lot of mosquitoes.) Eventually, her friend dared us to kiss. We did, although it was mostly banging teeth together. A sad start to my love life, but a propros for my eventual lovemaking style.

Why we stopped dating: We never actually started. I never really talked to Adrianna again after that first evening. I definitely told everyone she was my girlfriend though. But then we played against each other in this co-ed basketball tournament and Adrianna fucking lit us up for, like, 60 points or something. After that I was like, "Man, you know what, Adrianna, this just isn't gonna work."

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6 comments
kylebrooks1
kylebrooks1

Wow, what an insightful article..... Wait for it... Not.

GatoCat
GatoCat

Dude, you run while listening to... a tape? This may give us some insight into... ah, nevermind.

paulpsycho78
paulpsycho78

Young lovers entwined pass me by, and Heaven knows I'm miserable now

JustSaying
JustSaying

Its his 6 worst. Not his only six.

Daniel
Daniel

So you're 18? Relationships before about age 20 don't really count. These were in no sense "women."

J_A_
J_A_

Did you stop dating after 17 or are you 18 years old?

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