10 Celebrities Reveal Their Biggest Dating Disasters

Kelly Bryant | Feb 11, 2015 Celebrities
10 Celebrities Reveal Their Biggest Dating Disasters

Khloe KardashianCelebrities seem to have it all, so you'd think they'd have their pick of the litter in regards to incredible dates, right? Wrong. Even the rich and famous have had their share of dating disasters, and with Valentine's Day fast approaching, we've rounded up some of the most notable dating dilemmas of the stars.

What's your biggest dating disaster?

Image via Khloe Kardashian/Instagram

  • Khloe Kardashian


    Image via Khloe Kardashian/Instagram

    The ups and downs of Khloe's love life have been well documented on Keeping Up With the Kardashians, but one horrific moment she shared with a potential suitor is particularly bad. There she was, having a long-distance iChat with a guy she was seeing when suddenly their convo was interrupted. "A naked girl walks in the background and all of a sudden the computer just shuts, like stops,” Khloe told On Air With Ryan Seacrest. “And then he texted me an hour later, like, 'Sorry that was my sister,' and I was like, 'Uhhh.'"

  • Tina Fey


    Image via Peter Kramer/NBC

    Who knew that dating Tina Fey could be life-threatening? "One time a guy invited me to go mountain climbing on a date, and he fell off the mountain. He was showing off, and he just fell," she says. Eeks -- and that is why machismo can be a very bad thing, friends.

  • Paul Adelstein


    Image via Andrew Eccles/Bravo

    Paul Adelstein, currently starring in Bravo's Girlfriend's Guide to Divorce, has one of the creepiest date stories of all time. "Worst? I had a blind date during which the woman asked me -- an hour into it -- if she could cut me if we ended up having sex," he recalls. "I was trying to be calm, so I asked, 'With what?' She said, 'A knife.' And I said, 'Where?' And she said, 'Chest.' I said, 'Yeah ... no.' It was just crazy."

  • Katherine Heigl


    Image via Nino Munoz/NBC

    Katherine Heigl is married with kiddos now, but you won't believe the jerk who once took her to Sizzler. "I was, like, 20 pounds heavier and trying real hard to work it off at the gym and my trainer asked me out," she says. "He took me to Sizzler and gave me his head shot and asked me if I could get him in my agency. I knew it wasn't the extra 20 pounds that turned him on!"

  • Mindy Kaling


    Image via Mindy Kaling/Instagram

    No matter how bad the situation, we have a feeling Mindy Kaling can make anything sound hilarious, but she admits the worst ones she's encountered are the dates she doesn't even realize are a date. "The guy is like, let’s hang out, and it’s this nebulous thing, where you go to a matinee and are getting dinner afterward but you go Dutch," she tells Lucky. "And you were like, is this a date? I’ve had many of those in my 20s. So I pretty much think if a guy is willing to say, 'Do want to go on a date?' and actually uses those words, it’s probably not going to be that bad, because you know what the score is."

  • Nicole Kidman and Jimmy Fallon


    Image via Douglas Gorenstein/NBC

    Nicole Kidman's appearance on The Tonight Show Starring Jimmy Fallon was epic for so many reasons, but mostly because she outed him as being a horrible date. It seems the two had a pseudo-date back in the day, only Jimmy had no idea it was a date at all. Not only did he turn on a video game, but he also served her brie, corn chips, and leftover Chinese food.

  • Amber Riley


    Image via Amber Riley/Instagram

    Here's a tip if you plan on dating Glee's Amber Riley -- be punctual! "My last date was 40 minutes late," she told Glamour. "He was texting me that he was looking for parking, but [he took so long] I left. The only reason I even waited that long was because I was at the bar with my drink and tweeting." A girl after our own heart -- don't let that drink go to waste!

  • Jennifer Love Hewitt


    Image via Jennifer Love Hewitt/Twitter

    Seemingly unlucky in love for a long time, Jennifer Love Hewitt encountered one weird bachelor who not only brought her an 'N Sync backpack as a gift, but also sported a Donald Trump combover and snakeskin loafers. He then proceeded to take her to a batting cage (in the snakeskin loafers?) where he was hit by a ball and fell to the ground in tears crying for his mommy. As if that wasn't bad enough, he used his Altoids (he told her they were for when they smooched) to plant a goodnight kiss on her at the end of the night, proclaiming she could be the one. Sorry, man. Not gonna happen.

  • Christina Hendricks


    Image via SartorialPhoto/Splash News

    Mad Men's Christina Hendricks admits she's the one who almost ruined her first date with husband Geoffrey Arend by coming on way too strong. "I cracked it out [admitting her feelings] in such a big way," she says. "I was like, 'You make me want to have a family.' I freaked him out a bit ... Thank God I didn’t spook him enough to make him leave."

  • Kim Kardashian


    Image via Kim Kardashian/Instagram

    Before Kanye West was in the picture, Kim Kardashian had her fair share of bad dates, including her first meeting with former love Reggie Bush! "I picked him up from the car wash and then we ate Chipotle," she recounts. Hmmm, we still think Chipotle is a step up from that Waffle House double date Kanye took her on with John Legend and Chrissy Teigen.

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