Drew Barrymore & Luke Wilson
Drew Barrymore and Luke Wilson were the ultimate laid-back couple of the late ’90s. She’s said it was an open relationship, and that they were just “young, having fun, and not taking it too seriously.” They split after a few years but stayed friendly. Drew now hosts her own talk show and is raising two daughters, while Luke’s still working steadily in Hollywood.
Jewel & Sean Penn
In 1995, Sean Penn saw Jewel perform on Late Night with Conan O’Brien, got her number, and the two ended up dating for a short while. It’s the kind of unexpected pairing you forget happened until someone shows you a throwback photo. Their romance didn’t last long, but Jewel wrote about finding him “charming and witty” in her memoir. These days, she’s still touring and making music, and Penn’s still acting (and still making headlines).
Owen Wilson & Sheryl Crow
Owen Wilson and Sheryl Crow met on the set of The Minus Man in 1999 and dated for about two years. She even referred to him as “the love of my life” in interviews back then. They went their separate ways, and now Sheryl’s a mom of two and still performing, while Owen’s career is as strong as ever.
Will Friedle & Jennifer Love Hewitt
In 1997, Boy Meets World star Will Friedle brought Jennifer Love Hewitt as his date to the I Know What You Did Last Summer premiere. She later appeared on his show as his love interest, and they shared a makeout scene so intense that Friedle says it’s “uncomfortable” to watch now. It was short-lived, but pure ’90s teen star magic. Hewitt is now married with three kids, and Friedle’s been married since 2016.
