10 Occasions Celebrities Completely Failed At Flirting

Learn on to seek out out about these flirting fails…

1. Rachel Bilson

Lengthy earlier than Justin Timberlake was married to Jessica Biel, Rachel Bilson was “so obsessive about him” and determined to shoot her shot with the singer. Once they each ended up on the identical social gathering, Rachel says she tried to flirt with him — just for her buddy, Olivia Allen, to get in the best way.

“We have been kicking it with him. We have been making mates with him. [Rachel] went as much as him, clearly, or he got here to [Rachel]. I bought drunk and embarrassed myself a little bit as a result of he was attempting to flirt with Rachel,” Olivia recalled on the Broad Concepts with Rachel Bilson podcast. “That is the reality. You need the reality. I used to be drunk and I [sat] in between them. I used to be simply drunk and wished to maintain speaking to him.”

Sadly, with Olivia firmly planted between Rachel and Justin, there was “no room” for the pair to speak. Whereas Justin took the entire thing lightheartedly, Olivia admits she undoubtedly “embarrassed” herself and made the entire thing a fail for Rachel.

2. Chris Rock

When Chris Rock first met Rihanna, he determined he would attempt to flirt a little bit bit to see if she was inquisitive about him. Sadly, Chris says he shortly bought put within the “uncle zone.”

“I believed, ‘Hey, I am single now. Let me give it a go.’ You ever not understand how outdated you’re? Like, I could not inform how outdated I used to be… She did not even register me as a sexual being… I used to be, like, within the uncle zone,” Chris stated throughout an look on The Tonight Present.

3. Jennifer Lawrence

Earlier than Jennifer Lawrence was married, she ran into Larry David at Amy Schumer’s wedding ceremony in 2018. Wanting again, she says she tried to flirt with him all night time but it surely undoubtedly wasn’t reciprocated.

“I used to be flirting with Larry David all night time, but it surely was very one-sided. I’m obsessive about Larry David, however he isn’t obsessive about me. So after the ceremony, Amy grabs me and he or she’s like, ‘Let’s go upstairs and speak about life and love and [this giant decision].’ So we go as much as the roof and he or she’s, like, speaking about the whole lot, and I simply went, ‘Amy, each minute that I am right here, Larry might be leaving,'” she stated on The Late Present with Stephen Colbert.

4. Tiffany Haddish

Tiffany Haddish as soon as tried to make a transfer on Leonardo DiCaprio but it surely undoubtedly did not go based on plan. When she requested him if he would hook up along with her, he thought she was joking.

“I requested him if he’d let me hit that. He is like, ‘Tiffany, you are so humorous.’ I am like, ‘I am severe,'” she informed The Hollywood Reporter. “I informed him, ‘My solely stipulation: I wanna do it with you as your character in What’s Consuming Gilbert Grape.”

She continued, “He begins bustin’ up laughin’. ‘Why?’ he asks, and I say, ‘Trigger I really feel like that efficiency deserves an actual reward and that reward is that this.’ He begins goin’ into how he bought into the function, how he labored with these children and all these items, and I am simply listenin’ and listenin’, like, ‘Mmm-hmm, mmm-hmm.’ I lastly go, ‘All that’s good, I simply must know, When’s this gonna occur?'”

5. Nicole Kidman

A few years in the past, Nicole Kidman had a crush on Jimmy Fallon and a mutual buddy arrange a time once they might hang around. It seems that Nicole thought their meetup was a date however Jimmy had no concept that she was romantically inquisitive about him. The pair solely realized there had been a misunderstanding years later when Nicole made an look on The Tonight Present.

“So I am going over, and also you’re there in a baseball cap and like nothing. And also you would not speak. You would not say something, and then you definitely put a online game on or one thing and I am like, ‘That is so dangerous.’ And so after about an hour and a half, I believed, ‘He has no curiosity, that is so embarrassing’ … after which I left and was like ‘Okay, no chemistry.’ After which I used to be like, ‘Possibly he is homosexual,'” Nicole admitted.

6. Camila Cabello

Camila Cabello nonetheless remembers an award second with a crush when she was within the fourth grade. Wanting again, she says she was attempting to flirt along with her crush whereas watching a film with mates and by chance handed fuel.

“Once I was in fourth grade, I farted in entrance of my crush. It was terrible,” she informed Bop! Journal. “My crush and I have been watching a film collectively and he was sitting proper subsequent to me. I used to be so excited that he was sitting so near me. Then, out of nowhere, I farted proper subsequent to him. I panicked and blamed it on the chair I used to be sitting on, saying, ‘Oh, that was the chair!’ My buddy completely known as me out: ‘No, it wasn’t, you farted.’ It was actually embarrassing.”

7. Vanessa Bayer

Vanessa Bayer admits she bought a little bit too tipsy whereas attempting to flirt with a man she met when she was in school. Reflecting on the flirting fail, Vanessa says she wished to show she might drink simply as a lot as her potential associate however ended up throwing up on herself.

“There was a proper I went to in school the place I matched this enormous man drink for drink, after which I ended up throwing up on myself, however probably not understanding about it and being like, ‘We should always hang around extra.’ And he was like, ‘I am gonna go dwelling.’ After which I awakened a number of hours later and realized that I had thrown up throughout my costume. [I was like], ‘Oh, that wasn’t the good look,'” she informed Folks.

8. Gillian Jacobs

When Gillian Jacobs was in school, a gaggle of mates tried to introduce her to a possible suitor at a celebration. Sadly, chatting with him did not go so nicely and he did not appear to be responding when she tried to flirt.

“So I try to flirt, which for me normally was like, ‘I like public radio, how about you?,’ ‘Have you ever ever learn The Rings of Saturn by W.G. Sebald?,'” Gillian shared with Vogue. “Sadly, none of this gave the impression to be working. He wasn’t responding to me and he was barely even taking a look at me, and he was doing that God terrible factor at events the place somebody scans over your shoulder for anybody higher to speak to.”

9. Niall Horan

Early in Niall Horan’s profession, Katy Perry says she realized he had a giant crush on her. Actually, he tried to get her quantity a number of occasions — however she ended up rejecting his advances as a result of she thought he was too younger for her.

“I see [Niall] round on a regular basis, he is all the time attempting to, like, get my quantity to, like, possibly flirt with me, however I’m like, ‘I might babysit you. I am, like, your mother!'” Katy stated on Nova FM radio present Fitzy & Wippa.

10. Drake & Nicki Minaj

Drake has had a longtime crush on Nicki Minaj, and early of their friendship he tried to make a transfer on her. He made a flirty try for the pair to have dinner collectively however sadly it ended up being a fail.

“I bear in mind one of many first nights that we have been out in Miami and I went to Jerry’s [Famous Deli]. I used to be like, ‘[Nicki], you need meals, you hungry?,’ and he or she was like, ‘Yeah, I need some meals.’ I used to be like, ‘I am in, we gon’ eat meals collectively.’ I got here to her door and he or she took the meals and shut the door in my face! I used to be similar to, ‘Man, that is gonna be a protracted highway for us.’ I’ve all the time actually, truly, actually had a crush on her, all the time actually beloved her, and he or she’s all the time simply checked out me as, like, her little brother,” Drake informed MTV.