Once upon a time, when the internet still made those funny dialing noises and dinosaurs roamed the Earth (okay, maybe not the dinosaurs), Drew Barrymore—Hollywood’s favorite wild child—decided to grace the cover of Playboy. She was 19 and probably thought, “Eh, what could go wrong? It’s just a magazine, right?” Flash forward a couple of decades, and Drew is doing what every grown-up does best: reflecting on her teenage decisions and wondering, “What was I thinking?!”
The now 49-year-old actress, talk show host, and all-around queen of fun shared some of those spicy regrets on Instagram (because where else do celebrities spill the tea?). And, spoiler alert: it’s not just about her questionable choice in ‘90s fashion. It’s about that time she posed for Playboy like it was just a cute little photoshoot in your grandma’s backyard.
In her lengthy post on Friday (August 30), Drew decided to take a trip down memory lane, recounting her rebellious teenage years and, more importantly, why she’s now the world’s biggest anti-smartphone mom. Because let’s face it—if anyone’s kids should NOT be Googling their mom’s past, it’s Drew’s.
“I wished many times when I was a kid that someone would tell me no,” she wrote, presumably while side-eyeing her younger self. “I wanted to rebel so badly that I basically started a one-woman rebellion, fueled by unlimited access to everything and anything. Seriously, I had more freedom than a raccoon in a dumpster.”
She went on to explain how she was exposed to all sorts of “hedonistic scenarios” (which sounds like a fancy term for Hollywood parties that should’ve come with a PG-13 rating). These “highly sensitive” situations left her with something we all know too well: embarrassment that lingers like a bad hangover. “We, as kids, aren’t meant to see these images,” she continued. “And let me tell you, teenage Drew was a BIG exhibitionist.”
In true Drew fashion, she gave her Playboy moment a shout-out, saying she saw it as art at the time, and still does. “But in my early 20s, I posed for Playboy thinking it was just going to be this cute little print magazine that no one would remember.” Ah yes, because nothing says ‘this won’t come back to haunt me’ like appearing on the cover of one of the most iconic men’s magazines in history. Fast forward to the internet era, and Drew realized something the rest of us figured out after our first embarrassing Facebook photo post: images are FOREVER. The internet never forgets.
“I didn’t know the internet was coming,” she confessed. Let’s be real, Drew—none of us saw that one coming.
But despite the cringe moments, Drew made it clear she’s loving her life, mistakes and all. “We all make mistakes,” she said, “and honestly, people have been so nice to me about mine. It’s like they’re rooting for me to stop being a walking Pinterest board of questionable decisions.”
Now, as the mother of two daughters, Olive (12) and Frankie (10), who she co-parents with her ex-husband Will Kopelman, Drew is determined to be the responsible parent her younger self desperately needed. She’s basically the mom who’s mastered the art of “No, you cannot have a smartphone. Trust me, you do NOT want to see the stuff your mom did on hers!”
And honestly, if we could all face our teenage choices with the same humor and grace as Drew, the world would be a much funnier—and probably less awkward—place.
