It’s not every day that a steamy secret from the ’90s resurfaces on live television, but that’s exactly what happened on The Drew Barrymore Show when Drew Barrymore and Chloë Sevigny spilled some seriously unexpected tea.
The two Hollywood icons took a nostalgic stroll down memory lane, reminiscing about a night at the glamorous Sunset Marquis hotel in Los Angeles that ended in a surprising kiss in the bathroom. Yes, you read that right—Drew and Chloë shared a kiss, and it all happened 30 years ago during a night out that sounds straight out of a movie script.
The candid revelation came during a segment on the show as Drew and Chloë discussed her role in the groundbreaking 1999 film Boys Don’t Cry, which earned Chloë an Academy Award nomination for Best Supporting Actress.
But their story took an unexpected turn as Drew, with her signature mix of charm and enthusiasm, revealed there was more to that evening than just a good time. “We had a really amazing hang time at the Sunset Marquis hotel,” Drew began, setting the scene for what sounded like a typical Hollywood evening among friends.
“We were getting together, we had a long dinner. We were talking about a story that I was so passionate about, which ended up becoming a film that Chloë was not only in, but got nominated for an Academy Award for called Boys Don’t Cry.”
© Raymond HallBut Drew wasn’t finished. In a playful twist, she turned their long-ago memory into a trivia question for the audience.
With a cheeky grin, she set up a game where one lucky fan could win a $1,000 prize if they could guess what really happened in that bathroom that night—did Drew and Chloë share lipstick, toilet paper, or a kiss?
The audience waited in suspense as Jennifer, the participant chosen to answer, hesitated before taking a guess. “Lipstick?” she said tentatively. Drew smiled mischievously, leaving everyone on the edge of their seats.
“Well, it did involve lipstick,” she teased, while Chloë, adding a dash of 90s nostalgia, coyly chimed in, “It was the ’90s.” And then came the bombshell: Drew confirmed that she and Chloë had shared a kiss that evening—a playful, impulsive moment sealed with a hint of lipstick.
© Dimitrios KambourisDrew has never been one to shy away from being candid, and in a previous episode she opened up about a different kind of relationship—her love life today. When a fan asked Drew if she had any dating advice, she took a deep breath and thoughtfully considered her words. Looking directly into the camera, she spoke with heartfelt sincerity: “No matter how badly you've ever been hurt, you have to not believe that that is what is in your future or that someone else deserves that baggage.”
Her vulnerability was palpable as she continued, sharing wisdom not just with her viewers, but also with herself. “You have to be brave, and you just have to be convinced that each individual, circumstance, person, and situation is probably going to present [itself] differently,” she emphasized, offering a gentle reminder to anyone struggling to open up to love again. “It is not the repetitive fear that you have in your mind that you project,” she added softly, before pausing to conclude with a wry smile, “I’m talking to myself.”
It was a powerful moment of self-reflection that clearly resonated with the audience. Drew, who has been navigating the ups and downs of love for years, has been famously private about her romantic life since her split from art consultant Will Kopelman in 2016.
But, true to form, she surprised everyone last year when she revealed that she’s been in a relationship for around three years—something her fans had no idea about.
Speaking to Entertainment Tonight, Drew spilled a few more details about her mystery man, admitting that they met through the elite dating app, Raya. “I invited him to a wedding next weekend, and he said, ‘Wow, after three and a half years you are going to invite me to a wedding?’” she recalled with a laugh, hinting at just how private she’s kept this chapter of her life.
And it turns out Drew’s decision to bring her partner into the spotlight was inspired by none other than pop superstar Taylor Swift. Watching Taylor embrace her romance with NFL star Travis Kelce in front of the world, Drew found herself rethinking her own approach to dating. “There was something so normal about it,” she explained, clearly moved by Taylor’s no-nonsense attitude. “Obviously, Taylor Swift is everything but normal, but I’m a female, I’m going to go out on a date with a male, I’m not going to overthink this, I am not going to be the dark horse and be secretive and weird about it.”
For Drew, Taylor’s unflinching confidence was a revelation—a reminder that love doesn’t have to be complicated or hidden. “This was evidence of not being affected by what other people think,” Drew shared thoughtfully. “It was so calm, confident, and normal that it just made me think I should do this too.”
And it seems like this newfound perspective is working wonders. Drew’s happiness was palpable as she reflected on her romantic past and the many ups and downs she’s faced along the way. “I spent a lot of my life loving romance and drama and all of that,” she admitted to New York Magazine in a recent interview. “I just burnt myself out on it.”
After years of heartbreak and self-discovery, it’s no wonder Drew is cautious about jumping back into the whirlwind of romance. “I genuinely am tired and exhausted,” she confessed.
