1 of 12
WHEN MARTHA STEWART WENT ON A DATE WITH A GUY WHO LITERALLY RAN OFF AT THE END OF IT
She may be the ultimate lifestyle guru, but Stewart isn't immune to dating horror stories. "I went to the lounge area at Le Bernardin with this guy," Stewart said of the worst date she's been on. "He had to go somewhere afterward, and I had to go somewhere after. It wasn't a first date, but it was like a second or third date. We each had places to go; he did not ask me to go with him to the second place." She continued: "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."
2 of 12
WHEN KELLY ROWLAND FELL ASLEEP ON HER DATE
Way back in the day, Rowland accidentally napped during a movie date — and we aren't talking the cute, Sleeping Beauty-esque type sleep, either.
"I fell asleep on his shoulder, and I slobbered and snored," she said, according to The Huffington Post. "That was pretty bad. But he shouldn't have taken me to see There's Something About Mary for my third time. Whoopsie."
3 of 12
WHEN JIMMY FALLON DIDN'T REALIZE HE WAS ON A DATE WITH NICOLE KIDMAN
While chatting with the host on The Tonight Show, Kidman (finally) revealed to Fallon that they had been set up years ago to disastrous results. As the legend goes, Kidman had told her friend that she "liked" Fallon in that special way. "So Rick, our mutual friend, says, 'Oh, you know, Jimmy wants to meet you, and you can go over to his apartment," the actress explained. "And I'm single — I'm like, 'OK, yeah, cool!' "
"So I go over, and you're there in a baseball cap and like nothing. And you wouldn't talk," she continued. "You wouldn't say anything, and then you put a video game on or something and I'm like 'This is so bad.' And so after about an hour and a half, I thought, 'He has no interest, this is so embarrassing' … and then I left and was like 'Okay, no chemistry.' And then I was like, 'Maybe he's gay.' "
4 of 12
WHEN NIKKI REED MISTAKENLY THOUGHT SHE WAS ON A DATE
It was a very young fail, but it was a fail nonetheless. "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,' " Reed told Glamour. At least Reed's romantic life only went up from there. "That was probably my worst date ever!" she said.
5 of 12
WHEN JENNIFER ANISTON DIDN'T REALIZE JON STEWART HAD ASKED HER OUT
The two stars cleared up some decades long confusion when Aniston visited The Daily Show in 2010. "You come on the program and you're adorable," Stewart remembered of their first meeting. "And I asked you out. We went out, to an Italian restaurant. And it was lovely … I remember you brought so many of your friends.
"And I remember thinking, 'She's so excited to be on a date with me, she wants me to get to know her posse,' " he joked.
"That's really sad," Aniston replied. "But let me tell you, if I remember correctly — and maybe I'm remembering incorrectly — but wasn't it sort of like, 'Hey, a group of us are going out, do you want to join?' "
6 of 12
WHEN JESSIE J THREW HER BOWLING BALL THE WRONG WAY
Apparently, bowling isn't the safe bet date activity one might imagine it to be. Just ask Jessie J, who managed to thoroughly embarrass herself in the lanes. "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," she recalled, according to The Huffington Post.
7 of 12
WHEN BRITNEY SPEARS THOUGHT A GUY LOOKED LIKE A LIZARD & COULDN'T GET OVER IT
To be fair, even the least shallow among us have encountered physical features we just couldn't vibe with. But Brit was so put off by a suitor's reptilian resemblance that she just up and bailed on the outing.
"I have a friend at home and he randomly sets me up with people every now and then on dates. It's just awkward because there's so many times that you meet people and it's just too awkward and you just don't feel right," she said on The Jonathan Ross Show. "I went with this one guy and he looked like a lizard. Like I was so scared … I was like, 'Holy s---, he looks just like a lizard,' and I had to go. [I left] immediately."
8 of 12
WHEN KELLY OSBOURNE BROKE HER WRIST IN THE PROCESS OF GETTING HER FIRST KISS
In 2015, Osbourne told PEOPLE all about how her almost first kiss turned into a literal bloody disaster. "He went to kiss me and I got scared, because I was still very much a prude," she recalled. "I leaned back and fell down three stairs onto the street, broke my wrist and ran away from him."
"I still have the high-heeled shoes that I wore. They were yellow and at the toe, they had black and white stripes," Osbourne added. "They still have blood on them!"
9 of 12
WHEN KATE BECKINSALE WROTE HERSELF A POSTCARD FROM 'ROB LOWE'
Like all of us, Beckinsale did some embarrassing things back in her raging hormone days. But unlike us, the actress is brave enough to allow the Internet to delight in her teen yearnings. On Instagram, she shared a long-forgotten postcard that featured a portrait of Rob Lowe and the message: "Dear Kate yes I will marry you. See you soon. love Rob Lowe."
Beckinsale captioned the post: "EITHER I was a really tragic 13 year old with time on my hands OR Rob Lowe was all kinds of casual proposing marriage via a postcard of himself, signing his last name AND drawing a d--- instead of using a stamp. (found at my mum's house)."
10 of 12
WHEN VANESSA BAYER THREW UP ON A CRUSH BUT WAS TOO DRUNK TO NOTICE
The Saturday Night Live star has come a long way since her college days, which involved some very misguided attempts at flirting.
"There was a formal I went to in college where I matched this huge guy drink for drink, and then I ended up throwing up on myself but not really knowing about it and being like, 'We should hang out more,' " she recounted for PEOPLE. "And he was like, 'I'm gonna go home.' And then I woke up a few hours late and realized that I had thrown up all over my dress. [I was like], 'Oh, that wasn't the coolest look."
11 of 12
WHEN HELENT HUNT ASKED A FAMOUS MUSICIAN OUT BY LEAVING A NOTE ON HIS CAR
Hunt shared a studio lot with "Jessie's Girl" singer Rick Springfield while working on the sitcom It Takes Two as a teen. "He wouldn't date me but I was madly in love with Rick Springfield," she revealed on Watch What Happens Live. "I left a note on his car," she explained. "I left it on his windshield and somehow, he managed to not call me … I was so in love with him, you don't even understand."
12 of 12
WHEN CODY SIMPSON SPILLED POPCORN ON HIS DATE
"I spilled popcorn all over the both of us," Simpson told HollywireTV about his most embarrassing date moment. "I was just really clumsy. I was nervous." Fortunately, the singer's date wasn't the type to be completely fazed by the faux pas. "It was like a first date but luckily she was really relaxed and just had a great sense of humor," he shared.
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