Amusingly Horrible Things I Have Said: The Bracket

This is the last in a series of tournaments pitting the amusingly horrible things people have said to one another … against one another. This round turned out to be a little trickier than the past few (see: strangers, moms, bosses, significant others), with submissions skewing a bit more “horrible” than “amusing.” [Nervous laughter.] So we skipped the starting 32, and headed straight to the Sweet Sixteen! An impartial judge picked the “winners,” but the big “winner” still needs to be determined, if you’d like to vote. And yes, it’s not seeded; it’s unamusingly horrible; we’re idiots.

1. At my male (I’m a girl) best friend’s wedding, while drunkenly congratulating him and his bride: “Your uncle just told me he thought it’d be me.” She, rightly, still hates me.

2. My friend sarcastically asked me if I like her new “pixie” cut. I knew she was slightly unhappy with it. Me (totally slipped out): “Mmm, sort of reminds me of Javier Bardem in No Country for Old Men.” Friend: “That’s widely considered the worst haircut in cinema history.”

3. Past boyfriend and I are messing around in bed when my cell phone rings. I check caller ID and see that it’s my dad calling. BF, jokingly: “Tell him you can’t talk because your mouth is full.” Me, laughing: “It wouldn’t be all that full…”

4. “I can’t place your accent — where are you from?” “I’m deaf.”

5. “I think you should … you know … fix this,” I said, as I made gestures pulling my face back, indicating that I think my mother should get a facelift. 

6. What I meant to say: “I slay me!” after making a bad pun and laughing at it. What I said: “I kill myself!” in front of a guy whose mother had recently committed suicide.

7. A very short guy friend of mine introduced me to his new, tiny girlfriend, and I was genuinely thrilled for him. So much so that I gushed “Oh my god! It’s so great that you finally found somebody who’s shorter than … ahhh.”

8. On a booze cruise, I went up to my friend and his girlfriend. They’d been dating a long time and living together. I, being drunk, said to my friend, “Hey, when are you gonna ask this nice girl to marry you? Huh?!?” I pestered him about this for at least five minutes, asking his girlfriend, “When do you think he’s gonna ask you, huh???” She giggled and said, “I don’t know.” My friend looked a little upset, but I was too drunk to notice. I was later informed that he had already asked her to marry him several times, and she kept saying no.

9. Went into the bedroom/coat room at a party, where my friend had put her cats for the duration. Bumped into a an acquaintance who had recently finished a two-year prison sentence, and the first thing out of my mouth was the nonsensical yet totally offensive “OH MY GOD, CAT JAIL.”

10. Around Christmastime, I’m sitting on the C train at 86th Street station, and a well-dressed Upper West Side old lady laden with FAO Schwartz shopping bags decides to stick her arm in the closing doors so she can board the train in spite of the fact she’s too late and another train is right behind us. But instead of opening again, the doors remain closed around her arm. She’s wriggling to try to free herself for what seems like ages, and all the other passengers, including me, are beginning to panic that the train will take off with her still stuck in the door like that. We’re all picturing it dragging her along the platform, hearing the awful screams in our imagination. A couple of guys get up and start pulling on the doors, yelling, “don’t start the train, someone’s stuck!” and, just when we think she’s a goner, they finally open. She boards the train, and as she walks over to take a seat, my adrenaline still pumping, I yell to her: “I hope it was worth it!” Everyone stares at me. I hear someone say, “What’s WRONG with you?”

11. I met a boyfriend/girlfriend who had both been fired from their amazing dream jobs (at different places) the same week. “Ugh that sucks, but it’s also kind of cute?”

12. My new roommate, commenting on an old roommate she had a conflict with: “She said she didn’t like my aesthetic.” Me: “What aesthetic? … I mean, what’s not to like about your aesthetic?”

13. Me, a freshman in college, very tiny (it’s in my genes), to a friend: “I can’t believe you’re leaving school for an eating disorder! I mean, I think *I* weigh less than you!” Her: “…”

14. “At least you get some time off school.” Me, in a condolence card signed by my fourth grade classmates for a girl whose dad had died of a heart attack.

15. “Well, I don’t think you’re a very good writer.” In eighth grade, in response to my aspiring-writer best friend, who had (accurately) told me she didn’t think I could handle a séance, which I had proposed we conduct in front of the boom box that had mysteriously started playing an Adam Sandler tape.

16. “I can sort of see how he would leave you.”

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