Despite the 13-year age difference between them, model and actor Brooke Shields and Irish actor Liam Neeson were a pretty cozy item in the early ’90s. Shields reflected on their relationship in her memoir, as noted by InStyle, writing that Neeson “wooed [her] with his brogue, his poetry, and his s***** choice of cheap pinot grigio wine.” Their romance wasn’t to be for long, however. Shields also says in her book that Neeson proposed to her ring-less, then left town and ghosted her, then proposed again. She declined on the grounds that the Taken actor would probably fall in love with his next co-star and hang Shields out to dry. Neeson’s next co-star was Natasha Richardson, who went on to be his wife of 15 years until her death in 2009. RELATED: 32 Celebrity Couples With Huge Age Gaps. Being that Ben Affleck and Gwyneth Paltrow each have a handful of other high-profile celeb relationships in their past (and present), it’s easy to forget that they were a couple in the late ’90s. After starring together in Bounce and Shakespeare in Love, they went their separate ways. And despite both of them being major young stars when they were dating, the stir they caused was nothing compared to the media frenzy of Affleck’s next relationship with Jennifer Lopez. It appears that Paltrow was as excited as many of their fans to see Lopez and Affleck rekindle things this year—“Okay, this is cute,” she commented on a gallery of photos of them at a film premiere. Comic actor Owen Wilson and singer-songwriter Sheryl Crow may seem like an unlikely pair, but a pair they were. They met filming the 1999 movie The Minus Man, in which Crow made her acting debut and Wilson went dark, departing from his usual fare to play a serial killer. They split in 2001, but Crow memorialized their brief relationship in song—the track “Safe and Sound” from her 2002 album C’mon, C’mon is dedicated “For O” in the liner notes. They were both coy about it at the time, but Sandra Bullock admitted to Cosmopolitan years later that she and A Time to Kill co-star Matthew McConaughey did date for a while after meeting on the movie. And it seems like the breakup was fairly amicable. “I feel very cared for by Matthew,” Bullock told the magazine in 2003. “No matter where he is in his life or where I am in mine—he could be married—I know we would stay close.” Singer Seal seems to have an affinity for gorgeous supermodels. Before eventually marrying ex Heidi Klum, he was spotted with Tyra Banks at several big Hollywood events in 1996. Long before officially coming out in 2006, actor Neil Patrick Harris dated Christine Taylor. He told Howard Stern later that she was the “coolest, nicest chick ever” and his less-than-romantic feelings for her confirmed his suspicions that he was, in fact, gay. For more celebrity trivia sent right to your inbox, sign up for our daily newsletter. After guest starring in a 1996 episode of Friends as a love interest for Chandler, Julia Roberts briefly filled that role for Matthew Perry in real life. The pair were spotted on several dates later that year, though the relationship eventually ran its course. Just as Ryan Reynolds was beginning to emerge on the Hollywood scene, he met 3rd Rock From the Sun funnywoman Kristen Johnston and they began a romantic relationship that lasted a few months between 1999 and 2000. In a 2020 appearance on Watch What Happens Live, Johnston said it was so long ago she could barely remember the relationship, but that Reynolds was “a great guy.” Richard Gere and Cindy Crawford were one of the most famous (and attractive) couples to ever walk the red carpet together. They began dating in 1987 when Crawford was only 21 and Gere was 38—a 17-year difference in age that would eventually contribute to the end of their four-year marriage in 1995. Decades later, Crawford spoke about Gere on Marc Maron’s WTF podcast (via People), admitting that she had been too young then to truly fall in love. “And then, as I started kind of growing up and growing into myself—it’s hard to change the nature of a relationship once you’re already in it,” she said. When you think of Uma Thurman’s famous exes, Ethan Hawke, who she was married to from 1998 to 2005 probably comes to mind first. But Thurman was married to another well-known actor before that. She and Gary Oldman split after less than two years, and she later called their relationship “a mistake.” “We met when I was 18. He was 12 years older,” she told Vanity Fair in 1996. “It was a crazy love affair that ended, as it needed to. He was my first love. I had no prior experience.” *NSYNC singer Lance Bass and Boy Meets World star Danielle Fishel were the late ’90s teen idol power couple that dreams were made of. They even went to Fishel’s prom together. The two stayed friends after they broke up, Bass came out publicly in 2006. Last year, he told Fishel on his podcast (as reported by E! Online) that he “always knew” that she would accept him for that. Chris O’Donnell and Reese Witherspoon sparked rumors of a relationship when they attended an event on each other’s arms in 1993. A representative for O’Donnell told People at the time that they were “just friends” but that he “really lik[ed] her.” RELATED: The 18 Most Secretive Celebrity Couples of the Past 40 Years. Anne Heche and Ellen DeGeneres were one of the most visible lesbian couples in Hollywood when they dated from 1997 to 2000. In 2020, Heche said in an interview with Mr. Warburton magazine that while she hadn’t spoken to DeGeneres “in years” their relationship “was a beautiful part of my life and one that I wear with honor.” Matt Damon and Minnie Driver’s Good Will Hunting chemistry bled over into their personal lives, and the two were a pair for seven months after filming wrapped in 1997. It didn’t end well, however. Driver later said that she found out her relationship was over when Damon said he was single on Oprah. Christopher Wallace, better known as the Notorious B.I.G. and Faith Evans were married in 1994 after a whirlwind courtship. Tragically, B.I.G. was killed in 1997—and while the two were still married at the time, there were some issues of infidelity. Earlier this year, Evans spoke out disapprovingly about a Lifetime special on their relationship, which she says “sensationalized” the events that took places, especially B.I.G.’s affairs and the East Coast/West Coast rap wars. “How many times are people going to talk about that?” Evans asked Page Six, as reported by The Independent. Both Ashton Kutcher and January Jones were models before they were actors. They started dating in 1998, the year Kutcher would have his big acting break with That ’70s Show and a year before Jones would play her first role. They were broken up by 2001, and it seems that the overlap of their professional and personal lives may have had something to do with it. Jones told GQ in 2009, “The guy I was dating when I first got to L.A. was not supportive of my acting. He was like, ‘I don’t think you’re going to be good at this.’” While she didn’t name Kutcher, the timelines do line up. In the mid-’90s, after they both appeared in the film 8 Head Heads in a Duffel Bag, Saturday Night Live star David Spade was spotted out a few times with Buffy the Vampire Slayer (the movie) actor Kristy Swanson. As if their 1997 drama Inventing the Abbotts wasn’t dreamy enough on its own, it also marked the beginning of Liv Tyler and Joaquin Phoenix’s three-year relationship. They kept their love affair a secret from the rest of their coworkers during filming, but Tyler told The Morning Call that she “fell in love with Joaquin the second [she] saw him.” Though they eventually parted ways romantically, the exes are still good friends today. Drew Barrymore and Luke Wilson hit it off when filming their rom-com Home Fries, and it apparently worried their director. Dean Parisot told People at the time that he overheard “their first argument” on set, but ultimately, their personal connection made the movie better. “I swear to you, when he’s looking in her eyes they’re making up,” the director said of the scene they shot right after that. “And not only making up, they’re actually falling deeper in love.” The actors dated for two years before calling it quits. Ted Danson was still married to his second wife Cassandra Coates when he and Whoopi Goldberg struck up a romantic relationship while costarring in Made in America in 1992. The press ate it up, but by 1993, they were over—as were Danson and Coates. David Arquette and Alyssa Milano dated in the early ’90s, when the latter was closing out her run on Who’s the Boss. Milano confirmed their relationship in 2013, but she didn’t reveal many details. Courteney Cox and Michael Keaton fell in love in 1989, years before the former would hit it big with Friends, and conducted a remarkably private relationship. After six years of dating, though, the couple split. Shortly after the 1995 breakup, Cox spoke of her enduring fondness for Keaton. “It’s the most important relationship I’ve ever had, and I think he’s the most wonderful person I’ve ever met,” she told People. After meeting on the set of Everyone Says I Love You, Drew Barrymore and Edward Norton hung out romantically. The relationship started and ended within the same year, but they’ll always have 1996. A few years after Barrymore, Norton also dated Salma Hayek. Legend has it that they were set up by their chiropractor (!) and started seeing each other in 1999. While they made several red carpet appearances, they also tried to keep most of their relationship private. So of course, their 2003 breakup would be accidentally spilled by Hayek’s 11-year-old Spy Kids 3 co-star Daryl Sabara live on the Today show.ae0fcc31ae342fd3a1346ebb1f342fcb This indie power couple began dating in 1981—the same year that they formed the cult rock ’n roll band Sonic Youth—and married in 1984. Quite quickly, Thurston Moore and Kim Gordon became the parents of the indie underground, lending their guiding hands to the creation of other groups citing their band as an influence. Though, unfortunately, it seems all good things come to an end. In 2011, the pair announced the end of their relationship—and the end of Sonic Youth. Directors Spike Jonze and Sofia Coppola met in 1992, and for more than a decade, likely bonded over their affinity for directing beautiful and complicated indie films with impeccable soundtracks. After their divorce in 2003, the pair were rumored to have created tribute characters for each other in their films. TRL host Carson Daly and ingenue actor Jennifer Love Hewitt were one of the most ’90s couples the ’90s ever produced. Unfortunately, they had an awkward end. Daly told People (as reported by E! Online) that he found out they were broken up by hearing Hewitt say so on Howard Stern’s radio show. Vanilla Ice and Madonna hooked up back in the very early ’90s, and the rapper (real name Robert Van Winkle) claimed later that she was the pursuer. He’s also said that they broke up because he wasn’t pleased with her infamous 1992 book, Sex, nor how he was included in the suggestive photography. Singer-songwriter Fiona Apple and filmmaker Paul Thomas Anderson were one of the decade’s coolest and artiest couples, but they fizzled out after three years. In 2020, Apple opened up about the long-past relationship, calling Anderson a “coldly critical” and “contemptuous” partner. The pair met in 1991, married in 1992, and were divorced just two years later. Paula Abdul told People that the relationship ended because Emilio Estevez, already a father of two from a previous marriage, did not want any more children. The singer said the impasse was “heartbreaking for [them] both.” There was a magical attraction between Claudia Schiffer and David Copperfield—quite literally, at first. The couple first met in 1993 when he brought her up on stage to help with a trick. But, as it turns out, the spell only lasted until 1999, when the pair eventually called it quits. For actor Matt Dillon, there was just something about Cameron Diaz. They started dating in 1995 and starred together in There’s Something About Mary three years later—then broke things off after filming wrapped. RELATED: 16 Celebrity Couples You Didn’t Realize Aren’t Married.
