9 Celeb Dating Fails That’ll Make You Feel Less Sad About Your Own

Unless you’re one of those magical unicorn women who always finds herself in long-term relationships with a handsome, non-asshole boyfriend who you eventually dump for another long-term handsome, non-asshole boyfriend, dating can be rough.

But, there is a bright side to all this. Dating isn’t just rough for you, it’s rough for everybody, which includes celebrities.

Even though celebrities have enough money and influence to get out of most problems — a bad nose, a butt that just won’t plump, crushing that story about your coke use — they’re just as powerless as you are to make boys any less stupid.

Before you find your prince, you have to kiss a whole lotta frogs.

Here are 9 of our favorite celeb dating fails.

1. Olivia Munn

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Hot girls can make some guys nervous, and sometimes that nervousness manifests into some psycho behavior.

“We’re at dinner,” Olivia Munn explained, “and he picks up this steak knife and he says, ‘Can I count your teeth? You look like you have more teeth than the normal person.’”

Ummm, check please.

Source: Allure


2. Taylor Swift

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Boys don’t always handle break-ups that well, especially when they’re immature AF.

Talking about her breakup with Joe Jonas during an appearance on The Ellen Degeneres Show Taylor said:

“You know what, it’s like, when I find that person that is right for me, he’ll be wonderful. When I look at that person, I’m not even going to remember the boy who broke up with me over the phone in 27 seconds when I was 18.”

Classy, Joe.

Source: People


3. Kim Kardashian

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Even though Kim and Reggie Bush went on to have a marginally successful longterm relationship, their first date was embarrassingly lame. “I picked him up from the car wash and then we ate Chipotle,” Kim told Hollyscoop.

Damn was he lucky he was the more famous one at the time.


Source: Wetpaint

4. Karlie Kloss

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Once you hit puberty, being a tall leggy blonde really works out, but before everybody gets grown, your genetic advantages are just kinda awkward.

“In fifth grade,” Karlie Kloss recalls, “I went to meet a boy after school for an ice-cream cone, and I don’t think he spoke one word to me. I think he was a little nervous. I was a foot taller than him.”

Source: Allure

5. Kelly Rowland

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There is one thing that’s just as bad as falling asleep during sex — falling asleep during the middle of your date and drooling all over him.

“I fell asleep on his shoulder, and I slobbered and snored. That was pretty bad,” Kelly said, adding, “But he shouldn’t have take me to see There’s Something About Mary for my third time.”

Tell him, Kelly.


Source: Wetpaint

6. Nicole Kidman

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Sometimes, going on a date is like investigative reporting. You’re not really sure what’s going on between you two so you just have to dive in and go along for the ride.

Last year, Nicole Kidman told the story about how her friend set her up on a date with Jimmy Fallon, but apparently failed to tell him it was a date.

“You wouldn’t talk,” Nicole told Jimmy. “You wouldn’t say anything, and then you put a video game on or something…and so after about an hour and a half, I thought, ‘He has no interesting, this is so embarrassing’..and then I was like, ‘Maybe he’s gay.’”

Source: People 

7. Michael Kors

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It’s a well known fact that most boys have awful style, and while there’s a lot we’re willing to put up with, when he shows up to a fancy date looking like he’s about to go mow the lawn, you gotta hit him with that next button.

“I had a blind date with someone one,” Michael Kors recalls. “We went to a swanky Italian restaurant, and he showed up wearing cutoffs. I was like, ‘Maybe this isn’t going to work.’”

Source: Allure 

8. Lindsay Lohan

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Sometimes, when hot guys know they’re hot, they automatically assume every girl wants to have sex with them, and won’t wait for you to make the first move or even show that you’re interested, and hilarity ensues.

Lindsay Lohan recalled the following story to The Sun about the time Harry Styles tried to pull a move like this on her:

“He was in a suit. I said, ‘Well, you’re very good-looking — can I help you?’

“He was like, ‘I’m Harry. Gavin and Michael sent me here.’ I was in bed. I was like, ‘I’m going to bed but it was nice to meet you. It was 2 a.m., I had just come back from an AA meeting, I looked like shit too. I was wearing a big hotel robe, I had a slip under it. It was not a good look. I was watching some really cheesy movie too. You could totally hear it in the background.

“It didn’t click who he was at the time. I told my sister the next day and she was like, ‘Wait, are you kidding me? Do you understand? Do you have his number? Can I have it?’”

Source: The Sun 


9. Britney Spears

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And sometimes, the problem is just that he’s weird looking.

“I went out with this one guy, and he looked like a lizard. Like, I was so scared,” Britney Spears recalled. “I was like, ‘Holy s***, he looks just like a lizard,’ and I had to go. Immediately.”

Kissing toads is one thing, but lizards? Nah.

Unless you’re trying to gain entry into the Illuminati in which case, they’re all yours, honey. Say hi to Jay and Bey for me.

Source: People



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