5 of the Boldest Incidents of Celebrities Shooting Their Shot

Being a celebrity can be a real hassle — early call times, being stalked by paparazzi, deciding which designer to allow to dress you in the morning — but one thing it makes easier is picking up chicks and/or dudes. In fact, if you’re famous enough, you can get away with lines that would get normal people maced. Like when…
Michael Douglas Used the Cheesiest Pickup Line on Catherine Zeta-Jones
Imagine you lock eyes with a man across the room — a man 25 years your senior, no less — and when he walks over, the first words out of his mouth are “I want to father your children.” Instant drink in the face, right? Well, when you’re Michael Douglas, it’s instant Catherine Zeta-Jones at the altar. Don’t try this at “not the star of Basic Instinct.”
50 Cent Hit on Vivica A. Fox in His Acceptance Speech
If there’s any time to shoot your shot, it’s probably when you’ve just won one of the most prestigious awards in your field. At least, that was probably 50 Cent’s reasoning when, in the middle of accepting Best New Artist at the 2003 BET Awards, he announced, “I want to thank Vivica Fox for wearing that dress, too.” Again, that somehow worked, and they ended up briefly dating, though Fiddy later reflected that, “I gotta learn to shut the f--- up. Look at that look at end that’s trouble.” Whatever that means.
Jack Nicholson Stole Lara Flynn Boyle From David Spade Right in Front of Him
In the late ‘90s, the nightmare blunt rotation of Jack Nicholson, David Spade and Spade’s then-girlfriend, Lara Flynn Boyle, were being just that when Nicholson asked Boyle out right in front of Spade. He later said she was furious that he “didn’t stick up for her,” insisting she had no interest in Nicholson until Spade found out she’d left him for him when the National Enquirer called him for a comment on their recent appearance together. That must have hurt worse than the numbers for Dickie Roberts: Former Child Star.
Jennifer Lawrence Turned Jack Nicholson’s Line Right Back Around on Him
Nicholson has been at the other end of a bold move, too. After winning her Oscar for Silver Linings Playbook, she was speaking to the press backstage when she was interrupted by Nicholson, who praised her work but also commented that she “look(s) like an old girlfriend.” Without missing a beat, Lawrence quipped, “Do I look like a new girlfriend?” Nicholson itted that he “thought about it,” but nothing beside a bouquet of flowers and bottle of champagne ever came from the exchange. We hope.
Lizzo is Forever Drunk DM-ing
For whatever else she’s known for, shyness isn’t it, and that extends to Lizzo’s drunken social media hijinks. In 2019, she itted that she “slid into Drake’s DMs” before quickly unsending, though he followed her afterwards. Some real mixed signals there. Then, in 2022, she announced that she had drunkenly messaged longtime crush Chris Evans, imploring her TikTok followers to never “drink and DM.” Finally, after Niall Horan commented that he would never forget the bold comments she made upon meeting him backstage, she publicly replied, “Call me!”
May we all embrace our inner Lizzo. You know, in this very specific way.