The Most Ridiculous Thing You've Done to Impress a Crush

Apropos of nothing, I’ve recently acquired a bunch of teen magazines from the late ‘80s, ‘90s and early ‘00s. They’re a real trip to read in 2019, like visiting an alien planet, but one feature of the magazines exists throughout the decades: the “most embarrassing story” section. Usually the tale involves a tween girl a.) doing something weird and ridiculous to impress her crush, and having it backfire or b.) having something horrible happen to her in front of her crush. Also period stories, galore.

Naturally, I wanted to bring that chaotic energy to Pissing Contest. What absurd, ridiculous, embarrassing, silly, and/or cheesy thing have you done to impress the object of your desire? It doesn’t need to be from childhood, but those stories tend to be the most delightfully cringe-y. Who among us hasn’t put their dignity on the line for a potential smooch?

Before we get to all that, here are your winners from last week, the most absurd celebrity encounters of all time, probably:

According to Gabrielle Cynique, Joey Tribbiani is a standup dude:

I’m at the NBC studio store in New York. It’s maybe 1999? My favorite cousin was a HUGE Friends fan. I barely know Friends myself (I didn’t even own a TV at the time, because of being poor). So I went there to buy her some merch. I chose this giant Friends Central Perk latte mug. Seemed like a fun gift!

I’m leaving the store, just outside, when this guy hanging out about ten feet away says “What did you buy?” I’m a New Yorker. I was about to turn around and say “What the fuck does it matter to you what I bought?” But it’s Matt LeBlanc!

And he repeats his question and say “Hey, what did you buy?” And it’s so fucking mortifying, and I feel like such an asshole, but I hold up the box and say “Uhh…Friends latte mug.”

And Matt says “Do you want me to sign it?”

I say “You want to sign my mug?”

And he says “Yeah, do you have a pen?”

I dig into my backpack and find a magic marker. And Matt signs my mug, but almost immediately, the ink starts to bead, because a mug was not meant for signing. So he polishes it off with his forearm, and tries again. And it beads. And he tries again. And again. And again. And there’s no way this mug is going to accept ink from a magic marker!

By this point, the entire mug is this black smear of ink smudge, and Matt is covered in ink. His shirt, his arms, his fingers. He’s just swimming in ink, and my mug is looking just gross. And he’s deeply apologetic. But also I have this ink smeared Matt LeBlanc Friends latte mug that I just paid $50 for! And still, that’s kind of cool?

But Matt is so abashed and so sweet. And I’m still thinking that my cousin will be delighted to hear that this ink smear mug is the result of Matt LeBlanc’s failed and weirdly persistent attempts to sign it. (If he tried and failed to sign it 15 times, I don’t think I’m exaggerating).

Yeah, the mug is hot garbage. But I don’t really care. But Matt asks for my address. Promises he’ll make it right. I’m like “Whatever, it’s not a big deal. She’ll love the mug anyway!”

Two weeks later I got a huge gift basket of signed Friends merch from the entire cast and the sweetest note of apology from Matt LeBlanc.

KillerTomato, where was the camera?

Ron Jeremy getting a blowjob in a grocery store parking lot.

I pulled into a parking spot in a packed lot to go to pick up groceries and noticed that the car next to the driver’s side had the passenger door half open. I look in and lock eyes with Ron Jeremy and look down and see a woman standing outside the car and giving him head. Then I ran inside because I was grossed out and luckily they were gone when I left.

*shudder*

JujyMonkey: unstable genius, I’m going to need some context. Please:

I once played chess with Dave Mustaine, the lead singer/guitarist from Megadeth.

I won.

I like that Ewan McGregor can’t pronounce Foucault. Thank you for this information, Sheri Moon Zombie Strippers:

I worked at the Strand bookstore in New York in 2011-2012. One day, I showed up to work hungover and in a bad mood, and was waiting to talk to my manager about something when a guy tapped me on the shoulder to ask for help finding some books. In my surly state, I didn’t even look up at him, just rolled my eyes (probably) and went to go look up the books in our computer.

He said, in a very charming accent, “I’m looking for Discipline and Punish by Foo-Foocah-” struggling to pronounce the name. I cut him off very condescendingly like, “Do you mean Foucault?” As I said it, I looked up for the first time and realized I was talking to Ewan McGregor.

Y’all, I was mortified, but realized I couldn’t course correct my attitude too drastically or I’d look like an even bigger idiot who was only nice to people when I knew they were famous or something. So I just awkwardly helped him check the shelves (turned out the copy it said we had in the system wasn’t even there), dying inside the entire time.

He was absolutely lovely and polite to me the entire time, and said thank you even though I was of absolutely no help to him. I felt like a huge asshole, probably because I was. In my defense, I wasn’t usually such a jerk to customers, I was just in a terrible mood that day.

Ironically, when I was telling the story to one of my friends later, I realized I’d been mispronouncing Ewan McGregor’s name for years. So, take that, 22-year-old me.

All of EnglishSponge’s stories are dope. All of them:

Oh I have a few!

About ten years ago I was hanging out during my lunch break in Soho, near the clothing store where I worked as a lowly salesgirl. As I’m lighting my cigarette Selma Blair is suddenly next to me and asks to borrow my light. She then initiates an intimate conversation about her then boyfriend, who it seems jealous of her fame. She had tears in her eyes and it was actually a really cool, very NY moment

Another time, Zac Posen asked if my dress was Prada (it most certainly was a thrift store dress!) and I almost died from the thrill.

Also once I played a game of catch with Kim Kardashian and her nephew Mason in her hotel room while she wore a bathrobe. I accidentally hit her in the face with the little ball, but she was nice about it. Though, by that time I worked on a celebrity-adjacent field so it was slightly less weird.

New York is a hell of a town.

Marvinogravelbaloonface’s friend’s Santana run-in will hurt your heart, but in the best way:

Not me, but a friend. Working in a music store can get annoying quick because your day is filled with people who have no intention of buying anything but just want to come in then bash away on the instruments. My friend was working in the store in Marin County when a customer was wanking on an electric guitar that was out of tune. He walked up behind the customer and said in a snarky voice, “would you like me to tune that for you?“. The customer turned around and it was Carlos Santana

MargaretMoony, this is good:

I saw Sir Mix A Lot buying egg rolls at a local Thai restaurant in my hometown. That’s all I got.

Mrs. Fingerbottom, this tale, and U2, are both great:

This wasn’t me, but many years ago my aunt (in Dublin, Ireland) spent her lunch break from work in a nearby park. She sits down on a bench with her sandwich and a nice young man sits next to her. He is really friendly and they start talking. He introduces himself as Paul. She asks him what he does for a living, and he says he’s a musician. She immediately pities him a bit, thinking he’s a local struggling artist. She asks him if it’s difficult to make a living that way, and he smiles shrugs and says it’s ok. Still, my aunt offers him half her sandwich because she figures he must be hungry, because that is what Irish aunties do. She goes home later and describes the encounter and the man to the family and one of them says hang on, was this him? and shows her a magazine.

Anyway, it was Bono.

NPeartisnotmydad needs to write a memoir:

Working in hotels in NYC I met several B list stars. I brought a legit delivery of prescription drugs up to a completely out of it Paula Abdul who was on a tour with Milli Vanilli; I escorted a very drunk Loretta Swit to her room when she got lost in the hotel; the late Bobby Keys (legendary sax player for the Stones) asked where he could score weed; Axl Rose used to go by the code name of Quasimodo, if you called the switchboard and asked for that name, you were transferred to Axl; but the most surreal was when I was skating home and saw Lyle Lovett. I stopped and said hi and he was the most gracious and kind person, asking my name, etc. I did not know until the show that might that his new bride Julia Roberts was in the car waiting for him.

Get embarrassing in the comments below! I promise, it’ll feel freeing. We’re all friends here.