Khloé Kardashian delved into her family’s difficult dating lives while chatting on her new podcast on Wednesday.
The 40-year-old reality star shared on her show Khloé In Wonderland that men who try to slide into her DMs often make a disastrous mistake with her and her reality star–turned–actress sister Kim, 44.
‘If Kim gets a DM, we’ll say, ‘Did you get the same one?’ and we’ll check and normally we do,’ she admitted with a laugh. ‘I’m like, do you not think sisters are checking?’
‘How many times have we gotten the same DMs?’ she mused aloud to her friends Olivia Pierson and Natalie Halcro, who joined her for the episode. ‘We all check!’
Beyond simply being embarrassing, the double DMs are totally futile when it comes to Khloé, as she claimed she only favored relationships with people she had met in person.
She said she had ‘never ever’ bothered dating someone who tried to romance her via social media.
!['If Kim gets a DM, we'll say, 'Did you get the same one?' and we'll check and normally we do,' she admitted](https://chumzapp.com/wp-content/uploads/2025/02/1739446340_885_Kim-and-Khloe-Kardashian-reveal-one-of-the-biggest-mistakes.jpeg)
Khloé Kardashian, 40, revealed Wednesday on her podcast that men often try to slide into both her and sister Kim Kardashian’s DMs with the same messages. ‘If Kim gets a DM, we’ll say, ‘Did you get the same one?’ and we’ll check and normally we do,’ she admitted
‘Everything has been organic through a friend and if they’ve reached to me socially, I’ve been introduced because of a friend,’ she explained.
Khloé went further by sharing some of her dating horror stories with her guests.
One of her worst romantic prospects was a man she came to dub a ‘pee boy.’
‘I was dating someone — I can’t remember if we were intimate or not at this point, I’m assuming we were — and he slept over and he wet the bed,’ she admitted. ‘Just wet the bed.
‘And I was like, OK, that’s weird, obviously. ‘Cause we’re adults,’ she added.
The event was apparently so embarrassing for both parties that they stayed mum about it.
‘He never addressed it, we never talked about it, I was like, OK, maybe this didn’t happen, because we didn’t talk about it,’ she continued.
Khloé said she gave the man a second chance spending the night, only for him to wet the bed again.
!['Do you not think sisters are checking?' Khloé mused on her Khloé In Wonderland podcast. How many times have we gotten the same DMs?' she mused aloud; still from The Kardashians](https://chumzapp.com/wp-content/uploads/2025/02/1739446340_38_Kim-and-Khloe-Kardashian-reveal-one-of-the-biggest-mistakes.jpeg)
‘Do you not think sisters are checking?’ Khloé mused on her Khloé In Wonderland podcast. How many times have we gotten the same DMs?’ she mused aloud; still from The Kardashians
![Khloé added that it was futile because she has never dated someone who romanced her online and has only dated people she was introduced to in real life](https://chumzapp.com/wp-content/uploads/2025/02/1739446340_667_Kim-and-Khloe-Kardashian-reveal-one-of-the-biggest-mistakes.jpeg)
Khloé added that it was futile because she has never dated someone who romanced her online and has only dated people she was introduced to in real life
![She also outlined some of her dating horror stories, including one with a 'pee boy' who wet the bed both of the first two times he spent the night — and never said a word about it; still from The Kardashians](https://chumzapp.com/wp-content/uploads/2025/02/1739446340_837_Kim-and-Khloe-Kardashian-reveal-one-of-the-biggest-mistakes.jpeg)
She also outlined some of her dating horror stories, including one with a ‘pee boy’ who wet the bed both of the first two times he spent the night — and never said a word about it; still from The Kardashians
![Another mishap involved an attractive man she met in a hotel elevator. When they went up to a suite to get to know each other, he started 'hysterically crying over a cheeseburger' because he said she was 'such a nice person'; still from The Kardashians](https://chumzapp.com/wp-content/uploads/2025/02/Kim-and-Khloe-Kardashian-reveal-one-of-the-biggest-mistakes.jpg)
Another mishap involved an attractive man she met in a hotel elevator. When they went up to a suite to get to know each other, he started ‘hysterically crying over a cheeseburger’ because he said she was ‘such a nice person’; still from The Kardashians
!['Clearly these are not normal emotions because we have not done anything yet and we can’t even have a chat,' she said. 'I just remember being like, how do I get out of this place?'; still from The Kardashians](https://chumzapp.com/wp-content/uploads/2025/02/1739446340_660_Kim-and-Khloe-Kardashian-reveal-one-of-the-biggest-mistakes.jpeg)
‘Clearly these are not normal emotions because we have not done anything yet and we can’t even have a chat,’ she said. ‘I just remember being like, how do I get out of this place?’; still from The Kardashians
‘He’s peeing the bed like he’s a f***ing child,’ she recalled gossiping to her sister Kim.
From then on, the man was known as a ‘pee boy,’ though Khloé seems to have ended the relationship shortly afterward.
‘We don’t need pee boys,’ she laughed.
Another dating mishap involved a particularly attractive man she met in a hotel elevator who appeared to have some serious emotional regulation issues.
Their quick meet cute led the two to plan out a later meeting at a suite in the hotel to get to know each other — but he ended up turning on the waterworks.
Khloé couldn’t say if the man was ‘belligerently drunk’ or was suffering some other kind of crisis, but she revealed that he began ‘hysterically crying over a cheeseburger’ once they met up to chat in the suite.
According to her, he started crying after saying she was ‘such a nice person.
‘Clearly these are not normal emotions because we have not done anything yet and we can’t even have a chat,’ she said.
‘I just remember being like, how do I get out of this place?’ Khloé continued. ‘I have a grown man who’s crying over a cheeseburger, saying how great I am.’
The reality star’s Khloé In Wonderland podcast airs new episodes on Wednesdays at 9 a.m. on Elon Musk’s X platform (formerly Twitter), and other podcast platforms air the episodes beginning on Thursdays.