Khloé Kardashian Reveals Hilarious and Heartbreaking First Date Disaster with a Stunning Mystery Man
Khloé Kardashian is candidly sharing her most embarrassing date experience, giving fans a glimpse into her dating life.
In a recent episode of her podcast, Khloé in Surprise Land, which she co-hosts with friends Natalie Halcro and Olivia Pierson, the reality star candidly recounted a disastrous first date with what she described as the “hottest” man, a night that unexpectedly ended in tears — though not hers.
While Khloé chose not to reveal the identity of her handsome date or the specific timeframe of their encounter, she disclosed that their first meeting occurred in the elevator of a hotel, setting the stage for what was supposed to be a romantic evening.
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“I know Khloé’s worst date,” Halcro teased during the podcast. She dropped some hints about the story, mentioning the words “burgers” and “crying,” which piqued everyone’s interest and led to moments of laughter.
Khloé immediately recognized the reference and noted that the date was with the “hottest man,” while Pierson chimed in to describe him as “beautiful” and “so hot he might deserve another chance at love.”
“No matter how awkward the incident was, I feel like he needs a redemption,” Halcro added, sparking further conversation about how dating can be unpredictable and sometimes comical.
Khloé then finally revealed the dramatic details of what transpired on her disastrous date with the attractive stranger, captivating her audience.
“The worst date I’ve ever been on… we randomly met this man in an elevator. I was just being myself, super flirty,” she began, sharing her initial excitement about the date. “I said, ‘Hey, what’s your name?’ trying to keep it light and humorous.”
The Kardashians star continued by explaining that the man told her they were staying on the same floor, which led to them exchanging contact information. She noted that while they didn’t hang out immediately, he suggested they meet up again in another city, which she humorously bleeped out during the podcast.

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“He said, ‘Hey, I’m gonna be in [bleep]. I would love to hang out with you,” Khloé recalled, feeling optimistic about the potential for romance. “Cool,” she responded enthusiastically.
The mother of two shared that she was in the unnamed city with her sister, Kim Kardashian, at the time, adding an extra layer of excitement to the story.
“I hate to hear this,” Pierson interjected, building anticipation before Khloé revealed the details about their date, “You guys, he’s so hot.”
According to Khloé, when she and the attractive suitor finally met up, chaos ensued.
“I don’t know if he was belligerently drunk or if he was on something else, but we were like, ‘Let’s go meet at this suite upstairs so we can sit and talk,’” she recalled. “And this person is now hysterically crying over a cheeseburger, saying how nice I am. Clearly, these are not normal emotions since we hadn’t even done anything yet, and we couldn’t really have a proper conversation.”
“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 nice I am. I was planning on making out with you tonight, and it’s not happening,’” she continued, painting a vivid picture of her discomfort.
“Let’s have a smooch. I’m dying to, and it could not happen,” she added, expressing her frustration at how the evening had derailed.

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When Pierson asked Khloé how she ultimately “got out of there,” she shared that she had to make up an excuse to escape the awkward situation.
“I remember saying, ‘Oh my gosh. Our flight is in a couple of hours, I have to leave,’” she shared. “And I ran to Kim’s floor… Kim and Kylie were on the other floor. I was like, ‘I gotta get out of here.’ They were like, ‘What are you doing?’ I was like, ‘I’m hiding until it’s time for him to leave.’ Because I couldn’t handle it.”
Khloé mentioned she’s unsure if the man’s emotional breakdown was due to being “on drugs,” but emphasized that substance use is a significant “red flag” for her when it comes to dating.
“But he was so hot,” Halcro reiterated, prompting Khloé to agree, “So hot.”
“And I would absolutely want to hook up with you, like, if you weren’t crying, and weren’t on drugs, I’d probably hook up with you,” Khloé admitted with a laugh. “Just because you’re so hot. You can’t cry over a cheeseburger and expect me to be attracted after that.”
Pierson and Halcro chimed in, stating that the man “blew” his chance with Khloé, pondering if he might have been “nervous” during their encounter.

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In another segment of the Valentine’s Day-themed podcast episode, Khloé also revealed that one of her ex-partners had wet the bed multiple times during their relationship, adding to the laughter and light-heartedness of the discussion.
“I was dating someone. I can’t remember if we were intimate or not at this point. I’m assuming we were,” she recalled, setting the stage for a funny yet awkward confession.
“And he slept over, and he wet the bed,” she continued. “I was like, ‘Okay, this is weird.’ Clearly, because we’re adults,” she recounted, laughing at the absurdity of the situation.
The mother of two, who noted that they had presumably been “drinking” but weren’t “blackout drunk,” stated that the man “never addressed” the incident, leaving her to wonder if it had even happened.
Until it happened again.
“I remember the second time he slept over, he did it again!” Khloé told Pierson and Halcro. “I remember telling Kim, ‘He’s peeing the bed like he’s a f–king child.’ And yeah, so he was a pee boy.”
A few minutes later, Kim called Khloé, during which she asked her sister, “Remember Pee Boy, who wet the bed?”
“I was telling this story, and like, no one believes that someone wets the bed as an adult multiple times,” Khloé added, with Kim questioning if the man was “very drunk” during their encounters.
“It had to be,” she said, with Khloé noting, “Well, we hope so.”
See more from the podcast episode, here!










