10 Times Celebrities Totally Failed at Flirting

Read on to find out about these flirting fails…

1. Rachel Bilson

Long before Justin Timberlake was married to Jessica Biel, Rachel Bilson was “so obsessed with him” and decided to shoot her shot with the singer. When they both ended up at the same party, Rachel says she tried to flirt with him — only for her friend, Olivia Allen, to get in the way.

“We were kicking it with him. We were making friends with him. [Rachel] went up to him, obviously, or he came to [Rachel]. I got drunk and embarrassed myself a little because he was trying to flirt with Rachel,” Olivia recalled on the Broad Ideas with Rachel Bilson podcast. “This is the truth. You want the truth. I was drunk and I [sat] in between them. I was just drunk and wanted to keep talking to him.”

Unfortunately, with Olivia firmly planted between Rachel and Justin, there was “no room” for the pair to talk. While Justin took the whole thing lightheartedly, Olivia admits she definitely “embarrassed” herself and made the whole thing a fail for Rachel.

2. Chris Rock

When Chris Rock first met Rihanna, he decided he would try to flirt a little bit to see if she was interested in him. Unfortunately, Chris says he quickly got put in the “uncle zone.”

“I thought, ‘Hey, I’m single now. Let me give it a go.’ You ever not realize how old you are? Like, I couldn’t tell how old I was… She didn’t even register me as a sexual being… I was, like, in the uncle zone,” Chris said during an appearance on The Tonight Show.

3. Jennifer Lawrence

Before Jennifer Lawrence was married, she bumped into Larry David at Amy Schumer’s wedding in 2018. Looking back, she says she tried to flirt with him all night but it definitely wasn’t reciprocated.

“I was flirting with Larry David all night, but it was very one-sided. 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,'” she said on The Late Show with Stephen Colbert.

4. Tiffany Haddish

Tiffany Haddish once attempted to make a move on Leonardo DiCaprio but it definitely didn’t go according to plan. When she asked him if he would hook up with her, he thought she was joking.

“I asked him if he’d let me hit that. He’s like, ‘Tiffany, you’re so funny.’ I’m like, ‘I’m serious,'” she told The Hollywood Reporter. “I told him, ‘My only stipulation: I wanna do it with you as your character in What’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?'”

5. Nicole Kidman

Many years ago, Nicole Kidman had a crush on Jimmy Fallon and a mutual friend set up a time when they could hang out. It turns out that Nicole thought their meetup was a date but Jimmy had no idea that she was romantically interested in him. The pair only realized there had been a misunderstanding years later when Nicole made an appearance on The Tonight Show.

“So I go over, and you’re there in a baseball cap and like nothing. And you wouldn’t talk. 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,'” Nicole admitted.

6. Camila Cabello

Camila Cabello still remembers an award moment with a crush when she was in the fourth grade. Looking back, she says she was trying to flirt with her crush while watching a movie with friends and accidentally passed gas.

“When I was in fourth grade, I farted in front of my crush. It was awful,” she told Bop! 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. 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.”

7. Vanessa Bayer

Vanessa Bayer admits she got a little too tipsy while trying to flirt with a guy she met when she was in college. Reflecting on the flirting fail, Vanessa says she wanted to prove she could drink just as much as her potential partner but ended up throwing up on herself.

“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.’ 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,'” she told People.

8. Gillian Jacobs

When Gillian Jacobs was in college, a group of friends tried to introduce her to a potential suitor at a party. Unfortunately, chatting with him didn’t go so well and he didn’t seem to be responding when she tried to flirt.

“So I try and flirt, which for me usually was like, ‘I like public radio, how about you?,’ ‘Have you ever read The Rings of Saturn by W.G. Sebald?,'” Gillian shared with Vogue. “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 God awful thing at parties where someone scans over your shoulder for anyone better to talk to.”

9. Niall Horan

Early in Niall Horan’s career, Katy Perry says she realized he had a big crush on her. In fact, he tried to get her number a few times — but she ended up rejecting his advances because she thought he was too young for her.

“I see [Niall] around all the time, he’s always trying to, like, get my number to, like, maybe flirt with me, but I’m like, ‘I could babysit you. I’m, like, your mom!'” Katy said on Nova FM radio show Fitzy & Wippa.

10. Drake & Nicki Minaj

Drake has had a longtime crush on Nicki Minaj, and early in their friendship he tried to make a move on her. He made a flirty attempt for the pair to have dinner together but unfortunately it ended up being a fail.

“I remember one of the first nights that we were out in Miami and I went to Jerry’s [Famous Deli]. I was like, ‘[Nicki], you want food, you hungry?,’ and she was like, ‘Yeah, I want some food.’ I was like, ‘I’m in, we gon’ eat food together.’ I came to her door and she took the food and shut the door in my face! I was just like, ‘Man, this is gonna be a long road for us.’ 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,” Drake told MTV.