Celebrities Reveal Their Worst Date Horror Stories

We all know how dating can be and some dates are the worst—especially the first one! Even celebrities have trouble dating and their sometimes their fame doesn’t make them any more special than the rest of us. Read on to discover the worst date stories from your favorite celebrities!

Not Everybody Likes Britney Spears

It isn’t easy being the queen of pop. Britney Spears claims that a recent first date, going to the movies was a complete flop. Looks like her punchy tracks couldn’t impress her suitor, who she says wasn’t into her. Spears, who famously married a friend at the age of 23, and went on to wed KFed, says the date was “awkward”.

Britney told Marie Claire UK in 2016, “After the movie I came home and that was it. It just didn’t work. He just wasn’t that into me. I liked him. He knew that. But he definitely didn’t feel the same. It happens to everybody. Being famous doesn’t make you any different.”

Selena Gomez Takes First Dates Seriously

It could have been that she wasn’t over Justin Bieber (or another ex), but Selena Gomez got teary during a date. Upon arriving at a restaurant, Gomez started crying, perhaps putting a bit of a damper on the evening. She didn’t reveal too much to her suitor, aside from noting that the restaurant reminded her of a past relationship. Aww!

But that isn’t the only awkward moment she had on a date. Selena told Popstar! that one of her worst dates was with someone who was “very shy.” She went on to say, “So I was sitting there trying to ask questions and fill in the awkward spaces. I really like getting to know someone, so I love talking.”

Don’t Take Kelly Rowland To The Movies

The former Destiny’s Child artist, Kelly Rowland, while having no problem being vivacious on stage, supposedly fell asleep on a date. It happens to the best of us, right? Rowland describes a movie date, similar to Spears, that failed to light any sparks. To be fair to Kelly, she had already seen the film three times.

Kelly told Sarah Z. Wexler, who wrote Awful First Dates, “I fell asleep on his shoulder, and I slobbered and snored. That was pretty bad. But he shouldn’t have taken me to see There’s Something About Mary for my third time. Whoopsie.”

Ryan Gosling Is A Cryer?!

Ryan Gosling is not only the sensitive, loving boyfriend of our memes, but he is also that in reality. After hooking up with a date, Gosling shed a tear or two. When asked about the emotional outburst, Gosling admitted that sometimes, he just gets emotional. No wonder Eva Mendes is so crazy about him!

The woman who witnessed Gosling’s little outburst reportedly told Star magazine, “I thought I heard him sniffling. Then, I realized he had tears gushing down his face. I asked if he as all right, and he said he gets emotional sometimes.” Must have been a pretty awkward ending for that date!

Tori Spelling’s Messy Mishap

Once a teenage superstar, Tori Spelling took to her blog to recall a date so terrible that she vomited all over the restaurant kitchen! During her Beverly Hills, 90210 days, a then-unknown actor took her on a date to the hottest restaurant in town. But instead of ordering dinner, all her date ordered was drinks. Spelling writes, “I then selfishly prayed for breadsticks that would never come. He ordered us both Rum and Cokes. Oh no! I was a wine girl. I didn’t usually drink hard alcohol. But, I had to act cool, so I went with it.”

After stumbling around the restaurant to get to the bathroom, Spelling ended up in the kitchen where “A waiter rushed over with a massive copper saucepan where I proceeded to vomit the four rum and cokes and the cliff bar I had had at 11am into it. It was Donna Martin prom night all over again. I was mortified!” The date then had the audacity to call her two weeks later and ask if she could snag him an audition.

Even Martha Stewart Has Bad Dates!

Homemaking maven Martha Stewart recently came out with one of her terrible date tales. Apparently, some guy took Martha out to dinner but then he left her with the bill! Martha Stewart was having none of that.

On her show Martha & Snoop’s Potluck Dinner Party, she revealed, “I went to the lounge area at Le Bernardin with this guy. He had to go somewhere afterward, and I had to go somewhere after. We each had places to go; he did not ask me to go with him to the second place. We had cocktails and a little caviar or something. Then he just got up and said he had to run, and he ran out and didn’t pay! And I thought that was extremely rude.”

Portia De Rossi’s First Encounters

Even the beautiful, articulate wife of daytime star Ellen DeGeneres, Portia De Rossi, has had a few awkward hookup encounters. Apparently, DeRossi was so immersed during a hookup with an unnamed partner, she accidentally slipped and fell off the bed. Knowing DeRossi’s confidence, she probably just shrugged it off.

De Rossi admitted she struggled with her sexuality during her early days in Hollywood. In 2005, De Rossi is quoted as saying, “I didn’t want to be a lesbian. I’d never met one for a start and I just thought they were strange and that they hated men and they were very serious and I had these ridiculous images in my head and there were no out celebrities or politicians or anybody that I could look to and go, ‘Oh, I could be like that.'”

Nikki Reed’s Innocent Question

While she was bewitching on Twilight, the now-wife of Ian Somerhalder wasn’t always so lucky in love. Her worst date was actually not even a date at all, something she didn’t realize until the “date” was over. When she asked the guy if he wanted to go out, he turned her down. Ouch. Granted, she was only in second grade.

She told Glamour, “When I was in second grade, I went on a date with this guy. I thought it was a date, but he didn’t, and I wrote on a piece of paper, Do you want to be my friend or my boyfriend or nothing? Circle one. And he circled ‘nothing.’ That was probably my worst date ever!”

Salma Hayek

Meanwhile, as Nikki Reed’s dates don’t realize they’re on dates, actress Salma Hayek doesn’t realize she’s on them. During her first date with her now-husband, Hayek says that she didn’t realize he was considering it a date. She thought she was just going out with a friend, but it seems like the mistake worked out pretty well for them.

Hayek reportedly said, “My first date with my husband started badly. I didn’t know it was a date. I thought I was going to an event, and then there was just one person at it. I was set up by friends to think I was going to an event, because they knew I wouldn’t go on a date. I was angry. And he didn’t know, because he thought I knew he was coming just to meet him. It started out really badly. But as you can see, it ended happy.”

Taylor Swift Is Her Own Problem

Taylor Swift may come off as super confident in her songs, but even she can get a little awkward. After strongly pursuing a potential subject of one of her albums, Swift finally persuaded him to go out with her. Only once they went out on the date, she couldn’t stop talking about her cats.

Apparently, Taylor Swift is the reason that her dates don’t always end up working out. One source who reportedly dated Swift told Star that not only is Swift “super needy,” but that throughout their date, “She talked about her cats all night.” The date went on to speculate that that’s why Swift is a notorious serial dater—because all she cares about are her cats!

Kim Cattrall’s Worst Date Was At Work

Sometimes the best gift one can give is themselves, right? Not if you’re Kim Cattrall. The former SATC star recalls a guy who, rather than taking her out to dinner as promised, told her he was just going to watch her perform that night. On top of that half-baked attempt at a date, he was late, missing most of the performance anyway.

Huffington Post quoted Cattrall on the first date disaster: “I went out with an actor who said he’d come to see me in the play I was in and then we’d go out afterward for a drink or dinner. Then he called to downgrade it to nothing after, just him coming to my performance. He showed up at intermission.” Classy, dude.

Bear Grylls’s Heartbreaking Date Story

Adventure man Bear Grylls may be good at surviving in the wild, but perhaps not so much while going out in the wilderness for a date. The outdoorsman was stood up on a date he arranged, It was on the side of a mountain with a romantic picnic he prepared, and of course, carried up the hill. To make matters worse, there were three courses.

The date was recalled on Huffington Post: “I made a picnic up on a mountain for a girl, with tables and chairs and three courses. It took me a full day to carry it all up there. But then she never showed, and the wind and rain blew it. The whole night was a washout.” Our hearts are breaking for you, Bear.

No More Proms For Bad Gal RiRi

The singer was actually set-up by MTV to go to prom with a young fan, Richard, who didn’t have a date. Rihanna showed up in a stretch limo, dressed to the nines in a vibrant blue dress, however rather than letting himself enjoy it, Richard let the nerves get the best of him. He was so nervous, he couldn’t even make eye contact with her.

The prom date was probably so awkward that Rihanna didn’t want to relive it again. That’s why in 2015, she might have broken someone’s heart. An Instagram user asked her if she would go to prom with him if he could get 100,000 retweets on Twitter, even saying that he was a victim of bullying and panic attacks. What was Rihanna’s response? “No.”

Nobody Makes Amber Riley Wait

Want to make the former Glee star angry? Arrive for a date nearly an hour late. Amber Riley recalls her worst date was super late, and he didn’t even send a courtesy text until she was done with her first drink at the bar. Instead of waiting it out, Riley left.

The Glee star told Glamour, “My last date was 40 minutes late! 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.”

Dating Khloé Kardashian Comes With A Cost

The third Kardashian sister is a poet, and she doesn’t even know it. Oh wait, she totally does. Khloé Kardashian, known for her high-profile (ex) marriage to Lamar Odom, apparently likes to enchant her men with her poetry, or rather, her text poetry. One suitor, however, wasn’t amused and asked that she stop texting him nonsense.

Some people would even say that Khloé is one of the worst people to date. NBA player James Harden said, “I didn’t like all the attention. I feel like it was for no reason. I wasn’t getting anything out of it except my name out there and my face out there, and I don’t need that. It wasn’t uncomfortable, but it wasn’t me.”

Michael Kors Is A Fashion Designer, After All

First tip for dating a famous fashion designer? Maybe invest in a nice tie and jacket. The impeccable Michael Kors recalls a horrific date when his guy showed up… in a tank top and shorts. Kors, while appearing to be a pretty laid back guy, couldn’t accept casual to that extreme. He was humiliated.

Kors’s exact story is recounted on Huffington Post: “In my twenties, I went to meet my date at a really chic, fashionable restaurant. I wasn’t dressed up necessarily, but I had on a nice shirt and jeans. My date showed up in cutoffs and a tank top. I knew half the people in the restaurant, who were all looking at me like ‘Who is this guy with Michael Kors?’ It was so embarrassing. My tip: Always have your first date at a casual place.”

Kelly Is Not Impressed By Insecurity

Kelly Clarkson has also had her fair share of bad dates. And we suppose we should also mention that the first American Idol does care about height, as a lot of women do. One date that Kelly went on didn’t quite make the cut so Kelly felt the need to find a way out. What’s worse, is that he couldn’t stop talking about his height, which probably showed how insecure he was about the fact that she was an inch taller than him.

She told Ellen on The Ellen DeGeneres Show, “He proceeded to talk about his height for a solid hour. I withstood an hour. Then I went to the bathroom and I left.” How terrible!

Adam Levine Can’t Plan Dates

Although Adam Levine is attentive while sitting as a judge on The Voice, the lead of Maroon 5 can sometimes have the attention span of a puppy. On one date, he was so distracted by everything and everyone around him, the woman in his company didn’t feel like he was interested in her at all. She opted to call it a night.

Apparently Levine isn’t one to impress a woman on a date anyway. He once said in 2013, “I always like to dress up in a tuxedo and tell the girl to dress real fancy. I like to pick her up and go to McDonald’s in a tuxedo. You don’t have to shell out a bunch of money on the first date.”

Don’t Waste Tommy Hilfiger’s Time

Fashion designer and apparent heartbreaker Tommy Hilfiger cuts right to the chase. During a first dinner date with a young woman, Hilfiger decided she just wasn’t doing it for him. Rather than waiting it out, he made up an excuse on the spot and left immediately. Obviously, he didn’t give her a second chance.

Hilfiger told Huffington Post: “I was having dinner with a girl in a restaurant, and I was so incredibly bored — I had to get out. So I told her I had a business meeting I’d forgotten about and had to leave right then. I certainly don’t think she bought it — luckily I never talked to her again.”

Petra Němcová Doesn’t Like Narcissists

Supermodel Petra Němcová probably has to be around a lot of superficial people, and unfortunately, that included one of her dates. Němcová remembers a date that was so self-centered, he went on and on about himself the entire time they were out. Maybe he was just nervous?

Petra told Glamour, “I think the worst date is probably if the guy is just — and it did happen — talking about himself and how great he is! That’s just a great date. I just listened and nodded and smiled, but I left when I had to go. I always try to find the good in anyone, but [talking about yourself all the time] is not very attractive.”

Jennifer (Unlucky In) Love Hewitt

Everyone’s favorite 90’s horror movie scream queen, Jennifer Love Hewitt, apparently likes to talk about her nearest and dearest mother- a lot. During a date, Hewitt was a little too Mom-centric, going a little overboard talking about her mother, and even mentioning that she was walking around the area while the two were out.

That’s not the only terrible date that Jennifer has been on. She told USA Today, “I went out with a guy who’s a little bit older. I was 25 at the time, and he brought me an ‘N Sync T-shirt. Am I, like, 12? Most guys would bring flowers or chocolates. He gave me Altoids for our kiss at the end of the night, and we’d barely said hello. I found that so grody.”

Lauren Conrad Didn’t Need Her Parent’s Help

While now happily married and overseeing a fashion and lifestyle brand, The Hills star hasn’t always had the best luck in first dates. Her least favorite, and probably most awkward, was a date set-up by her parents. Conrad said they didn’t even complete a conversation. Can you hear the crickets?

That’s just one of the worst dates Lauren’s been on. On her blog, she writes of her worst Valentine’s Day: “A while back i was dating a boy and made the executive decision to take Valentitne’s Day into my own hands. I decided to surprise him with dinner at his favorite restaurant. Before dinner, I went and decorated the table – I set up all my presents and had a whole night of festivities planned. I had him meet me at the restaurant and when he showed up… he was drunk! It was really lame.”

Michael Douglas Makes A Bad First Impression

It’s a good thing that actor Michael Douglas has game, because he recovered from a pretty awkward first impression with his now-wife, Catherine Zeta-Jones. Douglas, who was already enamored with the actress, accidentally overplayed his hand at first by commenting about wanting to have children with her. They had literally just met.

He appeared on The Jonathan Ross Show, where he said he told Catherine, “You know, I’m going to be the father of your children.” She responded, “I’ve heard a lot about you and I’ve seen a lot about you and I think it’s time that I said goodnight.” At that point, he thought he blew it, but he obviously didn’t since they have now been married for over 20 years.

Don’t Take Jessie J Bowling

Singer Jessie J is a woman of many talents, but apparently, bowling isn’t one of them. During a first date with a guy, Jessie enthusiastically threw her bowling ball in the opposite direction of the pins. To make matters worse, a friend and their date had come along, so there was more than one witness to her clumsiness. Oops!

She told Huffington Post, “I went bowling on a double date… I got excited and I accidentally threw the ball the wrong way — backward. It was so embarrassing. They were like, ‘Yeah, she’s so uncool.'”

Ellie Kemper Doesn’t Like Blind Dates

Note to self: Do not set up Ellie Kemper on a blind date. While Kemper is positively delightful and cheery as the loveable Kimmy Schmidt, who she plays on The Unbreakable Kimmy Schmidt, she probably wasn’t as bubbly when she was forced to go out with a guy who acted annoyed by her presence. She described the guy as “rude”.

Ellie told Glamour, “The worst was a setup, a blind date. This particular guy was rude and was much older than I was. He seemed pained to be there. I was like, ‘Why would this person even want to go on a date?'”

Paul Adelstein Is Not Into Sadism

Most guys like it when a girl cuts to the chase, but the adorable Paul Adelstein isn’t one of them. Known for his roles in Private Practice and The Girlfriend’s Guide to Divorce, Adelstein was less than impressed with a woman who he took home started asking about his limits during sex.

Paul told Glamour, “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. 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.”

Ryan Reynolds Wasn’t Supposed To End Up With Blake

Ryan Reynolds met his wife, actress Blake Lively, when they were set-up on a first date… kind of. He was there with someone else and so was she. While they didn’t have much chemistry with the dates they brought along, apparently, the sparks flew between the future couple immediately. Which of course, made things so much more awkward for everyone involved.

Having met on the set of The Green Lantern, the two later went on a double date Reynolds revealed on a radio show: “We were buddies then. I remember it was funny because for about a year after Green Lantern had come and gone and all that stuff we were both single. We went on a double date. She was on a date with another guy and I was on a date with another girl. That was the most awkward date for [our respective dates] probably because we were just like fireworks coming across. It was weird at first but we were buddies for a long time. I think it’s the best way to have a relationship is to start as friends.”

Eliza Doolittle Doesn’t Like Groundhog Day That Much

Eliza Doolittle went out with a guy who perhaps had seen Groundhog Day a few too many times. A blind date actually repeated and copied nearly everything she said, from asking her how she was doing, to his actual food order. She admittedly she felt bad for him, but certainly wasn’t interested in repeating the date.

Huffington Post quotes Eliza’s story: “I went on a blind date, and after that I never, ever did it again. The guy repeated everything he said twice. He’d say, ‘So, how are you? How are you?’ and I’d say I was fine, and he’d say, ‘Good, good.’ Or ‘I’ll have the mac and cheese please, please. Yeah, the mac and cheese.’ I don’t know if there was something actually wrong with him or if it was just a bad habit, but no more blind dates after that.”

That Time DJ Khaled Proposed To Nicki Minaj

Nothing is more awkward than the person going ghost after asking them out, right? DJ Khaled knows this after he decided that a public display of affection was the right way to pursue Nicki Minaj. Khaled actually floated a proposal out there, on live TV, and maybe thought that would get her attention. Spoiler alert: It didn’t. Maybe try a text next time?

Dj Khaled took to MTV News and proposed to Nicki on live television. In his message to Minaj, DJ Khaled said, “I love you. I like you, I want you, I want you to be mine… We got the same symptoms we’re both suffering from success.” He even showed the camera a 10 karat diamond ring worth $500,000!

Christina Milian Cares About Oral Hygiene

Maybe when going out with a beautiful singer like Christina Milian, it would be wise to bring along extra breath mints. The singer remembers a date with breath so horrible, he had absolutely no chance at seeing her again. Milian described the smell as so pungent, that gum did nothing.

MadameNoire reported on Milian’s horrid experience: “I dated a guy who had really bad breath. Really bad. The elevator, the car, everything smelled like his breath. Even gum didn’t help!” We hope that the unfortunate guy didn’t attempt to kiss her! That surely would not have worked out so well.

Kim Kardashian Needs A Fancier Date Than That

Although happily and unavoidably married to Kanye West, Kim Kardashian is also known for a number of high-profile relationships. Her long-term relationship with football player Reggie Bush didn’t start well, with an awkward date that consisted of a trip to Chipotle.

Kardashian told the press about her first date with Bush: “We went to Chipotle and the car wash. I picked him up from the car wash and then we ate at Chipotle. Very sexy… My first impression of Reggie was, ‘this guy is so quiet. Why is he not taking my number? No!'”

Jared Leto Takes Acting Seriously

Jared Leto, known for his method preparation for roles, apparently doesn’t give it a rest even off set. During a date, Leto was preparing for an upcoming role in Alexander and chose to arrive for the date as his character… and remained in character. Since the girl he went out with wasn’t looking to go on a date with a historical figure, she wasn’t impressed.

Let’s just hope that he wasn’t trying to date anyone while filming Suicide Squad. Imagine the headspace that Leto had to get in to prepare for his role in that film! Also, it would be pretty terrifying if you went on a date with Leto’s portrayal of The Joker.

Ben Affleck Likes Big Butts And He Cannot Lie

Maybe when an actor goes out with another high-profile celebrity, it’s best not to videotape your dates. The booty rub seen round the world was all thanks to Jennifer Lopez’s music video “Jenny From The Block”, where the couple shared an intimate clip of Affleck rubbing her behind. Probably super weird for his daughters to see that now.

Even though Ben and Jen from back then were engaged, they unfortunately (or fortunately, depending on how you look at it) called it off. Affleck told GQ, “The amount of venom — I must have touched some specific little place in the consciousness… People decided that I was the frat guy, even though I’ve never been inside a fraternity, or the guy who beat them up at school, even though that wasn’t me at all.”

Lucy Hale Won’t Stand To Be Played

Many girls can relate to what Pretty Little Liars star Lucy Hale calls her worst date. During her first date with a guy, he thought he could get away with texting another girl under the table. Perhaps he didn’t know he was going out with the future Aria Montgomery because Hale totally called him out on it.

She told Glamour, “I was on a date with a guy once, and he wasn’t aware that I could see his cell phone — and the fact that he was actually texting romantic messages to another girl!”

Jay-Z Must Be A Very Patient Man

Before becoming everyone’s favorite couple, Jay-Z may well have been in the movie 50 First Dates during his courtship of his wife, Beyoncé Knowles. Make that 50 First Phone Dates. Rather than going steady immediately, the duo talked on the phone, as friends, for nearly two years before giving it a go. That’s patience.

Beyoncé told Oprah on OWN, “We were friends first for a year and a half before we went on any dates. We were on the phone for a year and a half, and that foundation is so important for a relationship. Just to have someone who you just like is so important, and someone [who] is honest.”

Andie MacDowell Should Keep Her Kids Away

Not even actress Andie MacDowell’s charm could save her from what could be the most awkward comment made on a first date. Fresh off a divorce, MacDowell had a younger guy pick her up for their first date. MacDowell’s daughter, taking notice of their age difference, apparently announced it out loud. Not a great first impression.

MacDowell recounted to Huffington Post: “It was very odd to start dating after being married for a long time and this was one of my first dates since the divorce with my husband. My date might have only been six or seven years older than me, but my kids see me as very youthful. He came to the door to take me out. My daughter was teeny tiny at the time, and she announced, ‘Mom, he is too old for you’ right in front of him.”

Ed Weeks Doesn’t Pick Up What You’re Putting Down

The charming Brit and The Mindy Project star, Ed Weeks, apparently has trouble reading signals with American girls. During a date, Weeks expressed how confusing it was for him to tell whether or not she was into him. He suspected that the girl wanted to keep him in the friend zone but still isn’t sure what happened.

Weeks told Glamour, “I misread the signals. Sometimes there’s a cultural gap. She was American, and I’m used to a certain set of verbal cues that one gets from the dating world. It was a bit of a disaster.”

LeToya Luckett Lost Her Chance

Once a singer of Destiny’s Child, LeToya Luckett may have thought she was hitting it off with NBA player Kevin Durant, until they weren’t. During a first date, a photo of the two was posted online, immediately revealing their night together and probably ruining it. Durant went on to date and eventually, propose to athlete Monica Wright. Thanks, Internet!

She later claimed that they just happened to be at the same restuarant together and that she had stopped by his table to say “hi.” While that is probably unlikely, we can see why she went through lengths to dispel the rumors. The Internet ruins everything!

Michael Fassbender Can’t Dance

While he’s certainly charming, Michael Fassbender isn’t the smoothest on the dance floor. During a film festival, he met his now-wife, Alicia Vikander, while dancing. Though they had a good start, Michael quickly revealed his less than impressive dance skills, while his wife blew him away with hers.

Vikander told Entertainment Tonight, “We had met at Toronto Film Festival and just on the dance floor. Fassbender added, “I thought [I was a good dancer] until she started dancing and then I felt like I had two left feet.” Luckily, Alicia didn’t hold his moves against him.

Toni Braxton Has Bad Blood With Shemar Moore

Nice exes don’t kiss and tell, unless someone once went out with Shemar Moore. After dating Toni Braxton, Moore decided it was appropriate to let everyone know that he hadn’t really been that serious about her. To really rub it in, he declared that he was still hung up on Halle Berry.

That would be pretty heartbreaking. Braxton was having none of it, apparently, as The National Enquirer reported that “Toni was ‘very upset over Shemar’s remarks,’ said a family insider, adding: ‘Shemar made it sound like Toni was chasing him just to have sex… She thought his comments were in poor taste, and when he compared her to Halle, that was just classless and disrespectful.'”