Stars Who Weren't Scared To Shoot Their Shot And Tried To Get With Their Fellow Celebs

Shooting your shot as a celebrity means the whole world could possibly watch you fail miserably.

Ayoub

• Published in Film & TV
• April 10, 2022

We see celebrities as pairs all the time, but we never get to witness the process of them getting together. It almost feels as if it is much easier for them to get into relationships with other celebrities, considering their status and fame but apparently, it is exactly the same for them as well.

Celebrities also have to shoot their shot and wish for the best and rejection or getting no response at all is also a very likely possibility for them. Some celebrities like to shoot their shots publically to make them more romantic and ballsy but the issue with such a move is that if you ever got rejected, that is also public and available for anyone to see and share.

Many celebrities are currently in long-term relationships because one of them was brave enough to take the first step, even publically, and let that other person know that they see a potential future with them. However, not all celebrities get that lucky match with one of their peers, but it is still worth the try nonetheless.

Scroll down and check out some of the ballsiest celebrities shooting their shots publically without having any fear or anything of the sort.

1. Drew Barrymore called Leonardo DiCaprio hot on Instagram

She spotted the opportunity and took it!

2. Drake giving Vanessa Hudgens a shoutout at the 2017 Billboard Music Awards.

As Drake accepted an award he said:

"We're all here on Earth for a limited amount of time, and we gotta show love while we're here. So tonight, I wanna say that, Vanessa Hudgens, you look incredible tonight,"

3. Lizzo admitted that she drunk texted Chris Evans

The DM consisted of 3 emojis, a gust of air emoji, the woman playing handball emoji, and a basketball emoji, basically implying that she's shooting her shot. Chris' response came later saying, "No shame in a drunk DM. God knows I've done worse on this app lol." 

Lizzo also started jokingly saying that she is pregnant with Chris' baby. He replied saying: "Hi! Just heard about our little bundle of joy. My mother will be so happy lol."

4. Diane Keaton kissed Justin Bieber on The Ellen DeGeneres Show

During a 2015 interview, Ellen showed Diane a photo of Justin modeling for Calvin Klein and Diane said: "That is gorgeous. Wow, I mean, okay, now we're talking," Justin came out from backstage and gave Diane a hug, and then she kissed him on the cheek.

5. Josh Hutcherson hunting for Emma Watson's number.

In a 2013 interview, MTV News reported that Josh said:

“I love Emma Watson. I’m dying to meet her,” he said. “I tried to get my manager to call, like, ... 'Could you, like, call Emma’s manager and see if we could, like, meet or something?’ It hasn’t happened yet. One day, fingers crossed!”

6. Adriana Lima asked Megan Fox if she could be her body double, so Megan told her that she needs a GF

The entire interaction between them is gold:

Megan replied, "But what if I need a girlfriend ... can I hit you up for that as well? 💜," and Adriana said in response, "It's a date see you tonight at Nobu."

7. Sebastian Stan flirting back-and-forth with his crush, Sharon Stone.

Back in 2016, both Sebastian and Sharon were guests on The Late Late Show with James Corden. It was then that Sebastian revealed his longtime crush on Sharon:

"I am geeking out a little bit because, you know, I've been meaning to tell you this for a while ... probably about 15 years, but ... I feel like I've seen you all my life," Sebastian said to Sharon. "And here you are in person, and you look so great."

Sebastian and Sharon kept flitting back and forth during that interview. Sharon even told Sebastian, "You are pretty cute, I just wanna throw that out there."

Later on, when the subject of headshots was brought up Sebastian said to Sharon: "You must have had some great headshots, c'mon ... There must have been some really great photographs."

8. Keke Palmer getting asked out by Bachelorette contestant Mike Johnson on TV.

"I don't like dating in the public, but if I were to ask you if we can go on a date, ... in public, ..." Mike said before Keke interrupted him, saying "What's the next question?"

They apparently never went on that date.

9. Julianne Hough wishing to be Daniel Radcliffe's valentine back when they were kids.

In 2012, Julianne said on LIVE! with Kelly that she tried to slip a love letter to Daniel when she was an extra Harry Potter and the Sorcerer's Stone, but things didn't exactly work out:

“I was kind of in love, especially with Daniel Radcliffe. I wrote him a love note,” Julianne said. “It was Valentine’s Day and I got him the Valentino Beanie Baby. I never heard back.”

10. Nicki Minaj informing everyone of her plans with Michael B. Jordan after the award show.

Nicki gave a shoutout to Michael while giving her acceptance speech at the People's Choice Awards in 2018, saying:

"Shoutout to Donatella Versace for custom-making this outfit for me, and shoutout to Michael B. Jordan, 'cause he's gonna be taking it off of me tonight."

11. Dua Lipa slid into Anwar Hadid's DMs, that's how they started dating.

In 2020, Lena Dunham and Dua Lipa were guests at Watch What Happens Live with Andy Cohen. They were asked if they ever slid into a celebrity's DMs:

"I have a confession to make ... mine was my boyfriend," Dua said. "We actually met at a barbecue, but it then carried on onto DMs."

Dua and Anwar are currently taking a break.

12. Lena Dunham slid into one of the Skarsgård brothers' DMs.

During the same interview with Dua Lipa, Lena said she once sent a DM to a Skarsgård:

"It was one of the Skarsgård brothers, and I can't remember which," she said.

13. Demi Lovato DM'd Emily Hampshire asking her out.

While on Demi's podcast, 4D With Demi Lovato, Emily Hampshire said:

“You slid in my DMs and you said, ‘Hey, I like you on the show. We should kick it sometime,’” “And then you said, below it, ‘And by kick it, I mean, like, go on a date. I find you attractive.’"

The two ended up becoming friends due to an age gap of a decade between Emily and Demi.

"I was like, ‘What’s the worst that could happen?’ And then I made a really good friend ... You’re a dope friend, and I’m happy that we became friends after that," Demi said. 

14. Rihanna Uncle-Zoning Chris Rock

Back in 2018, Chris talked on The Tonight Show Starring Jimmy Fallon about approaching Rihanna:

"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 ... [Rihanna] didn't even register me as a sexual being. I was, like, in the uncle zone," he said.

15. Nicholas Braun after Kim Kardashian's divorce

Back in 2021, Nicholas posted an Instagram video following reports of Kim and Kanye's divorce. He asked if Kim Kardashian would be open to dating a different kind of guy.

"Oh gosh. This Kim and Kanye divorce news is just bumming me out ... I'm wondering at this point, like, where do they even go from here?" Nicholas said before adding, "[Is Kim] willing to even take a shot on a new guy at this point? ... Would [she] be down to meet a new person, [a] totally just kinda different guy? ... or just a guy who's talking about it on the internet?"

Sorry, Nicholas, Pete Davidson beat you to the punch.

16. 50 Cent complimenting Vivica A. Fox on stage

50 Cent complimented Vivica A. Fox's outfit during an acceptance speech at the 2003 BET Awards:

"I'm just happy to be present for all of these beautiful people in here. You know, I wanna thank Vivica Fox for wearing that dress too."

This moment resulted in a romance that didn't last, but Vivica said 50 was "the love of [her] life" in a 2021 interview with DJ Vlad.

17. Betty White once flirted with Anthony Mackie

Anthony shared a story of when they met at a New York event, then approached her to express his admiration:

"I fanboyed out and ran up to her and was like, 'Oh my God, I love you so much, I'm such a fan. Like, the [Golden Girls] episode where you were tap dancing was so beautiful,'" Anthony said. "So, she laughed and touched my face and she says, 'Oh, you make me wish I was 40 years younger!' And I was like, I would do that."

18. A$AP Rocky asking Joan Smalls about her marital status.

In 2012, while being interviewed by RiFF RaFF alongside Joan at MTV VMAs, A$AP said: "You're beautiful. How you doin'? Ain't she beautiful?"

He then asked Joan about her marital status, and she said, "I'm not married, but I have a man. He's my hubby."

19. Meek Mill's thirsty comment on Kourtney Kardashian's Instagram thirst trap.

He is definitely not shy about showing his admiration.

All respect to these celebrities for putting themselves out there and shooting their shots. It's not easy to admit to liking someone in general, and doing it publically makes it a lot scarier, especially since you know that once something gets uploaded on the internet, you can never get rid of it and it stays there forever.

I assume there are probably many other private DM conversations that we never got to see of celebrities shooting their shots and trying to get with their dream person.

Ayoub