Khloe Kardashian is no stranger to the dating scene, but even the reality TV queen has her share of horror stories.
On the February 12, 2025, episode of her podcast, Khloe In Wonderland, the Kardashians star opened up about her experiences in the dating world, sharing what sends her running the other way.
In a candid conversation with guests Olivia Pierson and Natalie Halcro, Khloe revealed her worst date—a hilariously awkward encounter with an unnamed man that quickly turned into a cautionary tale. She shared,
“We were like, let’s go meet at this suite upstairs so we can sit and talk. And this person is now hysterically crying over a cheeseburger and crying because I’m such a nice person and clearly these are not normal emotions because we have not done anything yet and we can’t even have a chat”.
The Kardashians star didn’t hold back as she reflected on the bizarre encounter, identifying it as a glaring red flag in her search for a partner. She explained,
“I just remember being like, how do I get out of this place? I have a grown man who’s crying over a cheeseburger, saying how great I am. I don’t know if he was on drugs. Either way, if you’re on drugs, it’s a red flag, I don’t wanna be with you”.
Khloe Kardashian Spills More Hilarious Dating Horror Stories
The podcast host didn’t stop at just one cringe-worthy tale. In the same episode, Khloe recounted yet another bizarre and awkward date—one that even topped her previous story in terms of sheer absurdity.
Opening up with her signature humor, Khloe revealed,
“I was dating someone — I can’t remember if we were intimate or not at this point. And he slept over, and he wet the bed. Just wet the bed. And I was like, OK, that’s weird, obviously, cause we’re adults. He never addressed it. We never talked about it… So he was a pee boy. We don’t need pee boys”.
A few days prior to this revelation, on the January 22, 2025, episode of her podcast, Khloe opened up about her decision to embrace singlehood following her infamous split from ex-boyfriend Tristan Thompson in late 2021. She said,
“I’ve chosen not to—because I genuinely don’t want to—I’m not dating… Where I am in my life right now, I just really want to nurture this love and I just want to be as present as I can. I don’t want any distractions in my life”.
However, she quickly clarified that while she isn’t dating at the moment, she’s not entirely closing the door on future love. Khloe shared,
“If I meet someone in two months, two years and I fall in love—great. But I’m not actively on the dating scene searching for someone… I feel so fulfilled…”
Khloé in Wonder Land is back with a brand new episode as I'm joined by motivational speaker and #1 NYT bestselling author @JayShetty! Tune in LIVE on X now! pic.twitter.com/31bkHl6gi9
— Khloé (@khloekardashian) January 22, 2025
From cheeseburger tears to ‘pee boy’ mishaps, Khloe Kardashian proves that even reality royalty isn’t immune to dating disasters. Still, she’s embracing her independence and owning her narrative in her own words.