Macaulay Culkin & Friends Share Their Worst Dating Stories Ever On This Week’s Podcast

March 26, 2022 by , featured in Bunny Ears Podcast
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Welcome to an incredibly retro episode of the Bunny Ears podcast! This week, Macaulay Culkin sits down with his Season 1 cohost Matt Cohen (as well as Bunny Ear’s CCO Shawn DePasquale) for a fan favorite activity: LISTS! That’s right. The guys spend the hour ranking their “Worst Evers” in various categories (and full disclosure, some of these are really, really bad).

Mack, Matt, and Shawn begin by ranking their worst school moments. Shawn got slapped by a teacher, Mack split his pants in front of a girl he liked, and Matt freaked out like a baby during a class field trip … and that’s just the tip of the school-related living nightmares they share.

The guys then move on to “Worst Drug Experience”—of which they have plenty. Matt described the first time he ever smoked weed (he crawled through dirt and ended up in a cop car), Shawn had to babysit a new girlfriend on a terrible trip, and Mack took mushrooms then somehow composed and sent a 15-page email to every single person in his address book. And, much like with the previous category, there are many more stories of drug-induced youthful follies where that came from.

The trio round it all out by listing their top-three worst dating experiences of all time. These are so collectively cringe-worthy that we honestly don’t want to get into it here/relive them. So just listen for yourselves (thanks).

To get more of Matt Cohen, follow him on Twitter @cameltoad and check our Shawn DePasquale @shawnwrites. And, as always, get more Macaulay Culkin on Instagram here, Twitter here, and subscribe to his YouTube channel (where he posts a wealth of hilarious content) here.

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  1. Speaking of school times, I had gotten in trouble at Simpson County Academy (The school I was in at the time) and I was in Kindergarten class and the teacher spanked me for talking in class and spanked me because I said the Dear Darla quote from The Little Rascals.. She spanked me with a paddle and the paddle’s name was Buster!!!! And it really hurt, but basically I didn’t talk again for the next 10 years!!!!!

  2. OK…I give up…& YES I GOOGLED IT…who was the murderer GF from junior high that slapped you & had a tv show about her being a murderer…MAN~ i’m so behind in my knowledge of the 90s!!

  3. Hello everyone who cares or who bothers to read this. I don’t think I can top Mac’s story of the his date pooping on the floor. But here is a worse date experience. I was on a date with a guy who had issues shall I say. During our conversation, I ran from me and sat down on some cement steps. He then went into the fetal position and started crying. I must say this is a first, but it’s worth telling.

    My worse school experience was two kids knocked me down while a third pulled down my pants and underwear. Got to love showing your penis and bare butt to your classmates. I wanted to crawl into a hole and die. Looking back, I should have said to the girls–ok that will be fifty dollars. Seeing me naked is a privileged asset. I love you Macaulay Culkin!

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