Kim & Khloe Expose a Shocking DM Fail That Men Keep Making!
Khloé Kardashian recently got candid about her family’s dating experiences during an episode of her new podcast, Khloé In Wonderland. The 40-year-old reality star didn’t hold back as she shared surprising insights into the world of celebrity dating—especially when it comes to the do’s and don’ts of sliding into her and sister Kim Kardashian’s DMs.
According to Khloé, one of the biggest mistakes men make when trying to catch their attention is a lack of authenticity. “It’s so easy to tell when someone is copy-pasting the same message to a hundred other girls,” she said. “We see it all the time! It’s a major turn-off.”
Khloé explained that generic compliments or over-the-top messages rarely work. Instead, what really stands out are thoughtful, genuine notes that show the sender has taken the time to learn about their interests beyond just their public persona.
“Honestly, it’s not that hard,” Khloé added. “Just be real. You’d be surprised how refreshing that is.”
Her advice is not just for A-listers—it’s a universal tip for anyone navigating the modern dating world. As the podcast continues to share behind-the-scenes stories and relationship insights, fans can expect more unfiltered truths from Khloé, proving once again why she remains a fan favorite for her openness and honesty.
DM Fail: Men Think the Sisters Aren’t Comparing Messages
On a recent episode of her podcast, Khloé In Wonderland, Khloé Kardashian opened up about some of the cringeworthy and baffling direct messages she and her sister, Kim Kardashian, receive from men. The 40-year-old reality star revealed that one of the biggest dating faux pas guys make is sending the exact same message to both sisters—something they always catch on to.
“There are times when Kim will get a DM, and she’ll text me, ‘Did you get the same one?’ Nine times out of ten, I did,” Khloé shared, clearly amused by the lack of originality. “It’s almost like they forget we’re sisters who talk to each other every single day. Of course, we’re going to compare notes!”
For Khloé, these copy-paste attempts don’t just fall flat—they highlight a broader issue of authenticity. She emphasized that she’s never pursued a romantic connection with someone who reached out to her through social media. “I’ve never, ever dated someone who slid into my DMs,” she said. “Every meaningful relationship I’ve had started in real life, through natural interactions or introductions from mutual friends.”
Khloé explained that while social media can be a great way to connect with people, it’s not the method she prefers when it comes to dating. “If someone did reach out on social media, it was because a friend vouched for them first. There has to be a real connection—something genuine. I’m not into surface-level approaches,” she added.
Her advice for anyone trying to catch her attention? “Be real. Make an effort in person. Have a conversation. I appreciate when someone is thoughtful and takes the time to get to know me, rather than sending the same DM to me and my sister.”
Through her candid insights, Khloé offered a glimpse into the Kardashian sisters’ dating lives, showcasing how, despite their fame, they still value authenticity and genuine connections—something that a simple DM just can’t deliver.
Khloé’s Shocking Dating Horror Stories
Khloé didn’t stop at DM fails—she also dished out some of her worst dating experiences, including one that earned a former flame the nickname “Pee Boy.”
“I was dating someone—I can’t remember if we were intimate at that point, I’m assuming we were—and he slept over and wet the bed,” she revealed. “I was like, okay, that’s weird because we’re adults.”
To make matters worse, the man never even acknowledged the incident.
“He never addressed it, we never talked about it. I was like, ‘Maybe this didn’t happen because we didn’t talk about it,’” she recalled.
Giving him the benefit of the doubt, Khloé allowed him to stay over again—but the same thing happened.
“He’s peeing the bed like he’s a f***ing child,” she told Kim at the time.
From then on, the mystery man was forever known as “Pee Boy.” Unsurprisingly, the relationship ended shortly afterward.
“We don’t need pee boys,” she joked.
A Grown Man Crying Over a Cheeseburger?
Another bizarre dating mishap involved a seemingly charming man she met in a hotel elevator. After their brief encounter, they arranged to meet in a hotel suite later—but things quickly took an unexpected turn.
Khloé said the man began “hysterically crying over a cheeseburger.”
“I don’t know if he was belligerently drunk or having some kind of crisis,” she said. “But he just started crying and telling me I was such a nice person.”
Clearly overwhelmed, she immediately began looking for a way to escape the awkward situation.
“These are not normal emotions. We haven’t even done anything yet, and we can’t even have a conversation,” she said. “I just remember thinking, ‘How do I get out of this place?’”
Where to Listen to Khloé In Wonderland
Khloé Kardashian’s podcast, Khloé In Wonderland, has quickly become a must-listen for fans eager to hear behind-the-scenes stories and candid insights into the Kardashian family’s lives. Airing new episodes every Wednesday at 9 a.m. on Elon Musk’s X platform (formerly Twitter), the show offers an unfiltered glimpse into Khloé’s world—from dating misadventures to family dynamics and everything in between. For those who miss the live drop, episodes are also available on all major podcast platforms starting Thursdays.
In recent episodes, Khloé hasn’t shied away from discussing the hilarious and sometimes awkward dating situations she and her sisters encounter. One standout story involved men sending identical direct messages to both her and Kim Kardashian, a move that never goes unnoticed. “We always compare notes,” Khloé said with a laugh, adding that authenticity is the key to catching her attention.
Beyond sharing funny anecdotes, Khloé In Wonderland also touches on more personal topics, including motherhood, mental health, and how the Kardashian family navigates fame. Khloé’s genuine and down-to-earth approach makes listeners feel like they’re sitting down for a chat with a close friend. She often invites special guests, from family members to celebrity friends, ensuring each episode brings fresh perspectives and intriguing conversations.
As the podcast continues to gain popularity, fans are eager to see what revelations will come next. Whether it’s a juicy Kardashian family story or thoughtful reflections on life in the spotlight, Khloé promises to keep things real and entertaining.
With new episodes dropping weekly, Khloé In Wonderland is poised to remain a top choice for anyone craving a mix of humor, heart, and a little bit of Kardashian glam. Don’t miss out—tune in every Wednesday on X or catch the latest episode on your favorite podcast platform starting Thursdays!
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