Celebrities Dish On The Best And Worst Dates They’ve Been Set-Up On

Dating is strange, with a casual set-up leading to either an actual relationship or horrible flashbacks that plague you for months to come. And while celebrities look like they could have their pick of the pack, they’re no different than regular people.

From The Office’s Ellie Kemper being set up with a rude date to Cindy Crawford meeting her future husband through her agent, stars reveal some of their best and worst dating stories.

Jenny Slate Wasn’t Looking For A Literal Knight In Shining Armor

Jenny Slate Wasn't Looking For A Literal Knight In Shining Armor
Jim Spellman/Getty Images
Jim Spellman/Getty Images

When gals say they want a knight in shining armor, they don’t mean that in a literal sense. Actress Jenny Slate’s blind date didn’t get that memo, though, as he showed up to their date in full-on knight apparel, chainmail, and all.

During an interview with Talk Easy with Sam Fragoso, Slate said, “He comes around the corner inside the restaurant… this dude, and I’m not kidding, is dressed in full chainmail. He’s got a full authentic knight’s costume on, including a floor-length tabard, which I called a tunic, and then he corrected me and was like, ‘It’s actually a tabard.'” Wow, to be corrected in that situation!

Selena Gomez’s Date Was So Shy He Didn’t Speak

Selena Gomez's Date Was So Shy He Didn't Speak
Mustafa Yalcin/Anadolu Agency/Getty Images
Mustafa Yalcin/Anadolu Agency/Getty Images

There’s nothing worse than awkward silences, especially if that silence is with someone you just met. Well, for actress and singer Selena Gomez, nothing was worse than being set up with someone who was so intimidated by her that he didn’t speak! He was that shy.

During an interview with AceShowbiz, Gomez spoke of the instance, saying, “[The guy I went out with] was very shy, so I was sitting there trying to ask questions and fill in the awkward spaces.” At least it makes for a good story?

Michael Kors’ Piece Of Advice: Blind Dates = Casual Dinner

Michael Kors' Piece Of Advice: Blind Dates = Casual Dinner
Dimitrios Kambouris/Getty Images
Dimitrios Kambouris/Getty Images

For fashion designer Michael Kors, it took one horrible blind date to realize that any future blind dates weren’t going to be at a fancy restaurant where people from the industry go. In the book Awful First Dates, Kors explains his anti-fancy restaurant stance.

He said, “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.”

Bear Grylls Got Stood Up And Washed Out

Bear Grylls Got Stood Up And Washed Out
Stephane Cardinale – Corbis/Corbis via Getty Images
Stephane Cardinale – Corbis/Corbis via Getty Images

It might not come as a surprise that adventure man Bear Grylls opted to do an outdoor-themed date. The thing is, he went above and beyond what a typical guy does for a first date, bringing picnic supplies up a mountain the day before the actual date.

“I made a picnic up on a mountain for a girl, with tables and chairs and three courses,” he explained during an interview with The Huffington Post. “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.”

Britney Spears’ Blind Date With A Lizard-Looking Man

Britney Spears' Blind Date With A Lizard-Looking Man
C Flanigan/FilmMagic
C Flanigan/FilmMagic

The Princess of Pop, Britney Spears is anything but boring. And that goes for her love life, too. According to the singer, every time she’s able to make it back home, she has a friend who makes it their mission to set her up with people. Needless to say, they don’t all go well.

During an interview on The Jonathan Ross Show, Spears discussed how more often than not, the dates are just awkward. “there are so many times that you meet people and it’s just too awkward, and you just don’t feel right…I went with this one guy, and he looked like a lizard. Like I was so scared.”

Kelly Clarkson Used The Bathroom And Never Returned

Kelly Clarkson Used The Bathroom And Never Returned
Ethan Miller/Getty Images
Ethan Miller/Getty Images

One of the oldest “this date is going bad, and I need to bail” tricks in the book is excusing yourself to go to the restroom and never returning. Well, even singer Kelly Clarkson isn’t above pulling out the old trick when absolutely necessary!

According to the singer, her date talked about nothing but his height for a solid hour! Apparently, that was one hour too much. During a segment on The Ellen DeGeneres Show. Clarkson said, “He proceeded to talk about his height for a solid hour. I withstood an hour. Then I went to the bathroom, and I left.”

Ellie Kemper’s Blind Date Was Straight Up Rude

Ellie Kemper
Jim Spellman/Getty Images
Jim Spellman/Getty Images

The Office actress Ellie Kemper might be married to comedian Michael Koman, but once upon a time, she was being set up on blind dates. And for her, there is one that stands out above the rest. During an interview with Glamour, Kemper confessed that she had no clue what her friends were thinking when they set her up.

“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?'” nothing like going out on a date with someone who would rather be anywhere else!

Eliza Doolittle’s Blind Date Deterred Her From Future Blind Dates

Eliza Doolittle's Blind Date Deterred Her From Future Blind Dates
Mark Robert Milan/GC Images
Mark Robert Milan/GC Images

Something has to be truly awful to deter someone from it for the rest of their life. In singer Eliza Doolittle’s case, it took one blind date to make her realize she was never going to make the mistake of going on a blind date ever again.

According to the singer, her date said everything twice. During an interview, she said, “He’d say, ‘So, how are you? How are you?’ and I’d say I was fine, and he’d say, ‘Good, good.’…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.

Khloe Kardashian Didn’t Want To Go On A Blind Date With Tristan Thompson

Khloe Kardashian Didn't Want To Go On A Blind Date With Tristan Thompson
Jerritt Clark/Getty Images for Remy Martin
Jerritt Clark/Getty Images for Remy Martin

To say Khloe Kardashian and Tristan Thompson’s relationship is an on-going roller coaster of drama would be an understatement. Hey, maybe Brandon Jennings, the person who originally set them up, was banking on some good squabbling. Either way, the professional basketball player thought Khloe and Tristan would hit it off, so he introduced them at the KUWTK 10th-anniversary special.

During an interview, Khloe spoke of their blind date, saying, “I was at the Bel-Air hotel, and [Tristan] came to the dinner. I didn’t want to go on a blind date, so Brandon kind of ambushed the blind date. We just connected.”

Tori Spelling Drank To Pass The Time

Tori Spelling Drank To Pass The Time
Noel Vasquez/Getty Images
Noel Vasquez/Getty Images

If drinking to pass the time is part of a first date, it’s safe to say it’s not going too well. For Tori Spelling, a few adult beverages seemed like a better way to spend her time than listening to the one-sided conversation of her date, who wanted nothing more than to tell her about how he was robbed of a breakout role.

The 90210 actress actually wound up blogging about the experience, saying, “the room started spinning at this point, as he went on and on about how David Charvet robbed him blind from what would have been his breakout role on Baywatch.”

Kelly Rowland Wound Up Drooling On Her Date

Kelly Rowland Wound Up Drooling On Her Date
Robert Kamau/GC Images
Robert Kamau/GC Images

First dates are stressful enough without adding on to the awkwardness of falling asleep halfway through. Well, that’s exactly what singer Kelly Rowland did on one of her blind dates. Even worse, falling asleep was pretty mellow compared to everything else that happened! She spilled the tea during an interview with The Huffington Post.

Speaking of the date, Rowland said, “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.” Right, just blame it on the movie, Kelly!

Justin Bieber’s Night Ended In Pasta Sauce

Justin Bieber's Night Ended In Pasta Sauce
007/MEGA/GC Images
007/MEGA/GC Images

Nothing says messy first dinner, like accidentally spilling a plate of spaghetti on your date. For singer Justin Bieber, that’s exactly what happened! The “What Do You Mean” singer explained the incident during an interview with Cambio.

He said, “I took a girl out for a first date to an Italian restaurant and spilled spaghetti all over her. It was terrible and embarrassing. She never went out with me again.” It’s safe to say he didn’t win over his wife Hailey by spilling pasta sauce on her lap!

Lucy Hale Read Her Dates Signals All Too Well

Lucy Hale Read Her Dates Signals All Too Well
BG015/Bauer-Griffin/GC Images
BG015/Bauer-Griffin/GC Images

Going on a blind date can be awkward enough. It’s a new person who you’re trying to get to know and vice versa. Well, for Pretty Little Liars actress Lucy Hale, getting to know her blind date wasn’t exactly worth it. And for a very specific reason!

According to Hale, she went on a blind date with a guy who didn’t know the meaning of the word subtle. 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!”

Amber Riley Waited 40 Minutes Too Long

Amber Riley Waited 40 Minutes Too Long
ohn Wolfsohn/Getty Images
ohn Wolfsohn/Getty Images

When it comes to dating, punctuality is key, especially if it’s a first or blind date. You’re trying to make a good impression, after all! So when a date didn’t show up for a solid 40 minutes, Glee star Amber Riley packed her things and left.

“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.”

Salma Hayek And Her Future Husband’s First Date Started Badly

Salma Hayek And Her Future Husband's First Date Started Badly
CHRIS DELMAS/AFP via Getty Images
CHRIS DELMAS/AFP via Getty Images

Ironically, actress Salma Hayek had no clue she was being set up on a date the first time she met her future husband, Francois-Henri Pinault. In fact, Hayek’s friend told her she was going to an event! Little did she know that things were about to take an unexpected turn.

During an interview with Latina, Hayek explained the date, saying, “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.” Talk about miscommunication!

Elsa Pataky Met Chris Hemsworth Over The Phone

Elsa Pataky Met Chris Hemsworth Over The Phone
Albert L. Ortega/Getty Images
Albert L. Ortega/Getty Images

It’s almost as if actors Elsa Pataky and Chris Hemsworth were meant to be together, with how lovely they look with one another to the beautiful family they’ve created. Even so, they didn’t find each other on their own. They actually have their mutual dialect coach to thank for setting them up.

According to Pataky, their coach thought she and Hemsworth would hit it off. Finally, the actress agreed to speak with the Australian actor. “Finally, she insisted so much that I thought, ‘Okay, let’s meet.’ We talked on the phone, and we met.”

Jack Antonoff’s Sister Set Him Up With Lena Dunham

Jack Antonoff's Sister Set Him Up With Lena Dunham
Jamie McCarthy/Getty Images
Jamie McCarthy/Getty Images

Sometimes, siblings know best. At least, that was the case for Fun guitarist and drummer Jack Antonoff. The musician’s sister, Rachel, along with comedian Mike Birbiglia, decided he should meet the Girls actress, setting him up to go on a date with her.

During an interview with Vulture, Antonoff explained that he just spewed everything about himself on the first date, saying, “you really like someone; you want them to know everything about you.” The two stayed together from their initial 2012 meeting until their separation in 2017.

Ali Wentworth Was Set Up With A Friend’s Ex-Boyfriend

Ali Wentworth
Ilya S. Savenok/FilmMagic
Ilya S. Savenok/FilmMagic

On a scale of one to weird, a friend setting up another friend with their ex-boyfriend might be one of the strangest bits of dating imaginable. In 2001, actress Ali Wentworth somehow got conned by a friend to go out with her ex, ABC news anchor George Stephanopoulos.

According to an interview Wentworth did on The Tonight Show, she agreed with her friend, went on the date, and she and George both ordered the crab salad. Maybe there was something in the salad because the two were engaged two months later and married six months after that!

Tom Brady And Gisele Bündchen Knew Right Away

Tom Brady And Gisele Bündchen Knew Right Away
Taylor Hill/FilmMagic
Taylor Hill/FilmMagic

Tom Brady and Gisele Bündchen are two of the lucky ones who got swept up in a blind date that turned into love at first sight. Ironically, each of them agreed on the blind date after hearing a few simple words, “he/she is the girl/boy version of you.”

During an interview with Vogue, the supermodel said, “I knew Tom was the one straight away. I could see it in his eyes that he was a man with integrity who believes in the same things I do.” They’ve been happily married since 2009.

Cindy Crawford And Rande Gerber’s Bind Date Worked Out

Cindy Crawford And Rande Gerber's Bind Date Worked Out
Ron Galella, Ltd./Ron Galella Collection via Getty Images
Ron Galella, Ltd./Ron Galella Collection via Getty Images

It’s always nice to see when a set-up works out for two people. In this case, supermodel Cindy Crawford’s agent decided she needed a plus-one to his wedding, same with his friend, Rande Gerber. His solution? Set the two models up!

Meeting one another the day before the wedding, Crawford and Gerber hit it off, almost like they knew each other for a long time. According to an interview Gerber did with People, he was “surprised at how cool and down-to-earth she was.” The two have been married for decades now and have two children together.