01of 10WHEN TIFFANY HADDISH FLIRTED WITH LEONARDO DICAPRIO AND HE THOUGHT SHE WAS JOKINGMarion Curtis/StarPix/ShutterstockHaddish toldThe Hollywood Reporterall about her failed attempt to hook up with the actor when she ran into him at a party. “I asked him if he’d let me hit that,” she said. “He’s like, ‘Tiffany, you’re so funny.’ I’m like, ‘I’m serious.’““I told him, ‘My only stipulation: I wanna do it with you as your character inWhat’s Eating Gilbert Grape,“she continued.“He starts bustin’ up laughin’. ‘Why?’ he asks, and I say, ‘Cause I feel like that performance deserves a real reward and that reward is this.’ He starts goin' into how he got into the role, how he worked with these kids and all this stuff, and I’m just listenin' and listenin', like, ‘Mmm-hmm, mmm-hmm.’ I finally go, ‘All that’s good, I just need to know, When’s this gonna happen?'“When Haddish told the story again onJimmy Kimmel Live, she reiterated that she didn’t want her humor to distract from her real romantic intentions. “I don’t know if he thought I was playing, but I was dead serious,” she said.
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WHEN TIFFANY HADDISH FLIRTED WITH LEONARDO DICAPRIO AND HE THOUGHT SHE WAS JOKING
Marion Curtis/StarPix/Shutterstock

Haddish toldThe Hollywood Reporterall about her failed attempt to hook up with the actor when she ran into him at a party. “I asked him if he’d let me hit that,” she said. “He’s like, ‘Tiffany, you’re so funny.’ I’m like, ‘I’m serious.’”
“I told him, ‘My only stipulation: I wanna do it with you as your character inWhat’s Eating Gilbert Grape,“she continued.“He starts bustin’ up laughin’. ‘Why?’ he asks, and I say, ‘Cause I feel like that performance deserves a real reward and that reward is this.’ He starts goin’ into how he got into the role, how he worked with these kids and all this stuff, and I’m just listenin' and listenin', like, ‘Mmm-hmm, mmm-hmm.’ I finally go, ‘All that’s good, I just need to know, When’s this gonna happen?'”
When Haddish told the story again onJimmy Kimmel Live, she reiterated that she didn’t want her humor to distract from her real romantic intentions. “I don’t know if he thought I was playing, but I was dead serious,” she said.
02of 10WHEN JENNIFER LAWRENCE OBSESSIVELY FLIRTED WITH LARRY DAVID AT A WEDDINGYvonne Tnt/BFA/REX/ShutterstockThe Oscar winner has long been candid about her crush on theCurb Your Enthusiasmstar, and she finally got the chance to make her move atAmy Schumer’s weddingin February.“I was flirting with Larry David all night, but it was very one-sided,” she confessed onThe Late Show with Stephen Colbert. “I’m obsessed with Larry David, but he’s not obsessed with me. So after the ceremony, Amy grabs me and she’s like, ‘Let’s go upstairs and talk about life and love and [this giant decision].’ So we go up to the roof and she’s, like, talking about everything, and I just went, ‘Amy, every minute that I’m here, Larry could be leaving.'”
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WHEN JENNIFER LAWRENCE OBSESSIVELY FLIRTED WITH LARRY DAVID AT A WEDDING
Yvonne Tnt/BFA/REX/Shutterstock

The Oscar winner has long been candid about her crush on theCurb Your Enthusiasmstar, and she finally got the chance to make her move atAmy Schumer’s weddingin February.
“I was flirting with Larry David all night, but it was very one-sided,” she confessed onThe Late Show with Stephen Colbert. “I’m obsessed with Larry David, but he’s not obsessed with me. So after the ceremony, Amy grabs me and she’s like, ‘Let’s go upstairs and talk about life and love and [this giant decision].’ So we go up to the roof and she’s, like, talking about everything, and I just went, ‘Amy, every minute that I’m here, Larry could be leaving.'”
03of 10WHEN ZENDAYA’S FLIRTING PLAN WAS JUST BEING KINDA CREEPYMatthew Eisman/GettyThe Greatest Showmanstar lamented her terrible flirting technique onInstagram, sharing a message that read, “idk how to flirt imma just stare at you until u marry me.““Real [poop emoji],” she added in the caption. “It’s just not my thing.” Same, girl, same.
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WHEN ZENDAYA’S FLIRTING PLAN WAS JUST BEING KINDA CREEPY
Matthew Eisman/Getty

The Greatest Showmanstar lamented her terrible flirting technique onInstagram, sharing a message that read, “idk how to flirt imma just stare at you until u marry me.”
“Real [poop emoji],” she added in the caption. “It’s just not my thing.” Same, girl, same.
04of 10WHEN VANESSA BAYER THREW UP ON HERSELFJeff Kravitz/FilmMagicTheSNLstar learned the hard way that you should always check your outfit for vomit before approaching the object of your affection.“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 told PEOPLE. “And he was like, ‘I’m gonna go home.’ And then I woke up a few hours later and realized that I had thrown up all over my dress. [I was like], ‘Oh, that wasn’t the coolest look.'”
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WHEN VANESSA BAYER THREW UP ON HERSELF
Jeff Kravitz/FilmMagic

TheSNLstar learned the hard way that you should always check your outfit for vomit before approaching the object of your affection.
“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 told PEOPLE. “And he was like, ‘I’m gonna go home.’ And then I woke up a few hours later and realized that I had thrown up all over my dress. [I was like], ‘Oh, that wasn’t the coolest look.'”
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WHEN KATY PERRY CALLED OUT NIALL HORAN’S CONSTANT FLIRTING
Kevin Mazur/WireImage

“Niall’s amazing, I love him, and I think we feel very connected in a way because I, like, have helped him get throughThe X Factorto join his group,” she added.
Horan laterlaughed offthe flirting claims, (unconvincingly) insisting he just wants to be “friends” with Perry. “She’s just finding any excuse now to just patronize me and go around spreading rumors about me. I just want to be your friend,” he joked inTheProject. “I mean, she is talking like she is about 55 years older than me. She is not that much older than me.”
06of 10WHEN CAMILA CABELLO FARTED IN FRONT OF HER CRUSHBrian Ach/GettyAll of our flirting nightmares became a reality for the “Never Be the Same” singer. “When I was in fourth grade, I farted in front of my crush. It was awful,” she shared withBop!magazine.“My crush and I were watching a movie together and he was sitting right next to me. I was so excited that he was sitting so close to me,” she explained. “Then, out of nowhere, I farted right next to him. I panicked and blamed it on the chair I was sitting on, saying, ‘Oh, that was the chair!’ My friend totally called me out: ‘No, it wasn’t, you farted.’ It was really embarrassing … But now that I look back at it, it really wasn’t that big of a deal.”
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WHEN CAMILA CABELLO FARTED IN FRONT OF HER CRUSH
Brian Ach/Getty

All of our flirting nightmares became a reality for the “Never Be the Same” singer. “When I was in fourth grade, I farted in front of my crush. It was awful,” she shared withBop!magazine.
“My crush and I were watching a movie together and he was sitting right next to me. I was so excited that he was sitting so close to me,” she explained. “Then, out of nowhere, I farted right next to him. I panicked and blamed it on the chair I was sitting on, saying, ‘Oh, that was the chair!’ My friend totally called me out: ‘No, it wasn’t, you farted.’ It was really embarrassing … But now that I look back at it, it really wasn’t that big of a deal.”
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WHEN RIHANNA DIDN’T EVEN REALIZE CHRIS ROCK WAS FLIRTING WITH HER
Kevin Mazur/Getty Images

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WHEN DRAKE MISTAKENLY THOUGHT HE WAS EATING DINNER WITH NICKI MINAJ
John Shearer/BBMA2017/Getty

“I’ve always really, actually, really had a crush on her, always really loved her, and she’s always just looked at me as, like, her little brother,” the rapper added.
09of 10WHEN NICOLE KIDMAN DIDN’T TELL JIMMY FALLON THEY WERE ON A DATEDouglas Gorenstein/NBC/NBCU Photo Bank via Getty ImagesDuring aTonight Showappearance, Kidman finally clued Fallon into the fact that they had gone on a date years ago.The actress explained she had told her friend that she was interested in the funny man. “So Rick, our mutual friend, says, ‘Oh, you know, Jimmy wants to meet you, and you can go over to his apartment,” she explained. “And I’m single — I’m like, ‘Okay, yeah, cool!'““So I go over, and you’re there in a baseball cap and like nothing. And you wouldn’t talk,” Kidman 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.'”
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WHEN NICOLE KIDMAN DIDN’T TELL JIMMY FALLON THEY WERE ON A DATE
Douglas Gorenstein/NBC/NBCU Photo Bank via Getty Images

During aTonight Showappearance, Kidman finally clued Fallon into the fact that they had gone on a date years ago.
The actress explained she had told her friend that she was interested in the funny man. “So Rick, our mutual friend, says, ‘Oh, you know, Jimmy wants to meet you, and you can go over to his apartment,” she explained. “And I’m single — I’m like, ‘Okay, yeah, cool!'”
“So I go over, and you’re there in a baseball cap and like nothing. And you wouldn’t talk,” Kidman 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.'”
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WHEN GILLIAN JACOBS TRIED TO FLIRT AT A CLUB
Robin Marchant/Getty

In avideoforVogue’s “Sad Hot Girls” series, Jacobs recounted a time her college friends introduced her to a potential date during a night out. The actress used the opportunity to put her finest flirting skills to the test, and they were decidedly lacking.
“Sadly, none of this seemed to be working. He wasn’t responding to me and he was barely even looking at me, and he was doing that godawful thing at parties where someone scans over your shoulder for anyone better to talk to,” she continued.TheIbizastar and the mystery man ended up parting as friends that night.
source: people.com