10 SHOCKING Times Celebrities Took FLIRTING Too Far

Awkward Attraction: The Most Uncomfortable Celebrity Interviews Ever

Some celebrity interviews get awkward—but sometimes, they go way beyond that. From billionaires getting handsy to A-list stars getting flustered on live TV, these moments prove even the most polished celebrities can’t always keep it professional when attraction and awkwardness take over. But as you’ll see, not everyone gets away with it. Stick around—the last story is a breakup the whole world saw coming.

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Billionaire Gone Too Far

In what might be one of the creepiest interviews of all time, billionaire Richard Branson sat next to Salahek on Conan and took things way too far. Branson, with all his charm and billions, crossed boundaries—grabbing Salahek and throwing him onto his lap on live TV. Conan tried to lighten the mood, but you could feel the discomfort in the air. Even Conan threatened, “You touch her one more time, I’ll rip your head off, pal. I don’t care how much money you have.” In the ‘90s, moments like this often flew under the radar. Today, they’d go viral for all the wrong reasons.

Chris Rock and Sofia Vergara

Before Sofia Vergara was a household name, she appeared on Late Night with Conan. Chris Rock’s jaw nearly hit the floor. He couldn’t believe his eyes, making one hilarious comment after another, mixing shock and admiration. But as funny as it was, the moment showed how quickly interviews can derail when celebrities let their guard down.

Charlize Theron’s Crush

Charlize Theron wasn’t hiding her feelings when she admitted to having a massive crush on Michael B. Jordan during a game on Ellen’s show. Ellen made it interesting by surprising Charlize with Michael B. Jordan himself during her next appearance. Charlize was so stunned she refused to let go of his hand. It was one of those moments where you could feel the secondhand excitement.

Shaq and Roxy Diaz

Shaq was supposed to be promoting his suits company, but he couldn’t help teasing Roxy Diaz about being in his DMs. The playful banter was so open it felt like a comedy sketch. But sometimes, the flirting goes too far.

Russell Brand Crosses the Line

Nobody crossed lines quite like Russell Brand. During a late-night interview, he wasted no time trying to flirt, even physically moving toward the guest as Jimmy tried desperately to block him. The audience was left half laughing, half cringing.

Chemistry That Spills Over

Sometimes, the chemistry between co-stars spills into interviews. Hailee Steinfeld and Michael B. Jordan’s playful energy was fun to watch, but her Spider-Man co-stars’ attempts at flirting came off much more awkwardly.

Tom Hiddleston and Scarlett Johansson

Tom Hiddleston found himself in an awkward situation with Scarlett Johansson, interrupted mid-sentence by the Black Widow herself.

Henry Cavill and Double Standards

Henry Cavill, known as Superman, has spoken openly about how male actors often face unwanted physical attention that would never be acceptable if the roles were reversed. Being a massive guy doesn’t mean he enjoys people putting their hands on him during interviews and on set.

Justin Bieber Confuses Sushi

Justin Bieber met model Irene Kim, and the flirtation was instant—even if he accidentally confused sushi for Korean food, which was its own awkward moment.

Drake and Nicki Minaj

There was a time when Drake and Nicki Minaj were inseparable on stage and in interviews, fueling rumors of romance. Ironically, they would end up beefing years later, turning what looked like a love story into hip-hop drama.

50 Cent Gets Flirty

During an interview, a female host surprised 50 Cent with a custom chain. He flirted back, turning the moment into a viral exchange.

Sebastian Stan and Anthony Mackie

Sebastian Stan made a beeline for an interviewer he clearly liked, and Anthony Mackie jumped in like the ultimate wingman, teasing about matching her dress to Stan’s eyes.

Sarah Shahi and Craig Ferguson

Sarah Shahi brought unmistakable flirty energy to The Late Late Show with Craig Ferguson, hinting at lessons she wanted to learn from him.

Britney Spears’ Pregnancy Reveal

During Britney Spears’ pregnancy reveal on Letterman, Dave, embroiled in a cheating scandal, cracked a risky joke implying he might be the father. Britney shut it down instantly, to the audience’s delight.

Ariana Grande Meets Jim Carrey

Ariana Grande grew up idolizing Jim Carrey, even using the username JimCarreyFan442. When she finally met him, she couldn’t help but cry on camera—a sweet, genuine moment.

Sydney Sweeney and Glen Powell

When Sydney Sweeney and Glen Powell promoted their romcom, fans noticed undeniable chemistry—even though both were engaged. Social media exploded with clips of their flirty interviews, leading to Glen’s relationship crumbling. Sydney revealed on a podcast that a single phone call before visiting him on set became a breaking point. Glen’s fiancée was bombarded with tags, and eventually, the relationship ended.

Chris Evans and Ana de Armas

Chris Evans and Ana de Armas share incredible on-screen chemistry. During interviews, it was clear Chris was captivated by Ana’s Portuguese skills, getting adorably flustered on camera—a favorite among fans.

Celebrity interviews are supposed to be professional. But as you’ve seen, sometimes they turn into moments that are awkward, hilarious, or even a little uncomfortable to watch. From billionaires crossing lines to superstars revealing crushes, these moments prove that no matter how famous you are, the human side still shows.

Which of these moments shocked you the most? Drop it in the comments. And if you enjoyed this, check out our video on celebrities who shut down disrespectful interviewers. You’ll see just how quickly things can flip when the tables turn. Until next time, stay curious.