Yes, this really happened. The celebrity hook-ups you just won’t believe but don’t blame your memory, when it comes to Hollywood, there’s a lot of celebrity breakups and divorces, and it can be hard to keep up.
From Brad Pitt’s social life pre-Gwyneth Paltrow (let alone his subsequent marriages) to the celebs who were once engaged, lived together or just hit a few red carpets in all their dewy glory, the world is full of stars who found each other for at least a little while, long before social media was around to document their every move.
Click through for a trip down memory lane with the stars you totally used to ship.
Winona Ryder & Matt Damon
It wasn’t just a Gen X fever dream, they really dated.
Brad Pitt and Juliette Lewis
They played doomed lovers twice, in 1990’s Too Young to Die? and 1993’s Kalifornia, but in real life they had a perfectly lovely relationship.
“I still love the woman,” Pitt, who was Lewis’ date to the 1992 Oscars when she scored a Supporting Actress nomination for Cape Fear, told Vanity Fair in February 1995. “There’s some real genius there. I had a great time with her…It was one of the greatest relationships I’ve ever been in. The problem is, we grow up with this vision that love conquers all, and that’s just not so, is it?”
Mandy Moore & Andy Roddick
This was them: The U.S. Open champ courted the A Walk to Remember star between 2003 and 2004, but ultimately it wasn’t a love match.
“He broke my heart,” Moore told Howard Stern in 2018. “I was a kid, he was a kid. I started dating him when I was 18.”
Dave Coulier & Alanis Morissette
You oughta know by now that one of the most enduring mysteries in music history is who inspired Morissette’s iconic 1995 single—and the Full House star is at the top of the list of maybes! Morissette denied it in the 2021 documentary Jagged, but that’s a tough pill to swallow.
Alanis Morissette & Ryan Reynolds
Two Canadians, a ring and a trip to the altar that never happened, but we hear the breakup was very polite.
Blake Lively & Leonardo DiCaprio
Before she found her forever-mate in Ryan Reynolds, the Gossip Girl star had a summer of fun in 2011.
January Jones & Jason Sudeikis
You can’t blame the Mad Men star for liking funny guys.
Minnie Driver & Matt Damon
The Good Will Hunting stars paired off in real life, too, but they didn’t drive off into the sunset together.
“Well, I’m single,” Damon said on The Oprah Winfrey Show in January 1998. “I was with Minnie for a while, but we’re not really romantically involved anymore. We’re just really good friends, and I love her dearly….I care about her a lot. We care about each other a lot. It wasn’t meant to be, you know? And if it’s not meant to be, then it’s not meant to be.”
The pronouncement was a bit too public for Driver’s taste. “It’s unfortunate that Matt went on Oprah,” she told the LA Times later that year. “It seemed like a good forum for him to announce to the world that we were no longer together, which I found fantastically inappropriate.”
Helen Mirren & Liam Neeson
The two began dating after meeting on the set of the 1981 movie Excalibur. They lived together for years before they split in the mid-’80s.
Jeff Goldblum & Laura Dern
Finding love in Jurassic Park? Talk about a meat cute.
The co-stars quietly began after filming the 1993 blockbuster, with Goldblum telling The Chicago Tribune at the time, “I was struck, I’d been a big fan of hers. I think she’s an amazing actress, and a spectacular person. I was struck from the beginning. But after the movie we realized we liked each other.”
Though they got engaged in 1995, the pair ultimately split two years later. But they reunited on-screen for the first time in Jurassic World: Dominion, the sixth installment in the franchise.
Gillian Anderson and Peter Morgan
The X-Files alum was in a relationship with The Crown creator between 2016 and 2020. ICYMI, she played Margaret Thatcher in the Netflix hit in 2020.
David Arquette and Ellen Barkin
According to Arquette, the two dated while filming their 1995 Western Wild Bill.
Jeremy Sisto & Reese Witherspoon
The Clueless actor confirmed a little-known rumor during a Reddit AMA chat in November 2015, revealing that he used to date the actress. The two had starred in the 1992 TV movie Desperate Choices: To Save My Child.
“She was my first actress girlfriend,” he said. “We had a long distance relationship for a long time. I was so into her.”
Bethenny Frankel & Eric Stonestreet
E! News exclusively broke the news that the Real Housewives of New York star and Modern Family actor were a pair in 2015. But by the following year, they had split.
Regina King & Malcolm-Jamal Warner
The Southland alum and the actor, who played Theo Huxtable on The Cosby Show, dated for several years before calling it quits in 2013.
Kelly Preston & George Clooney
The famous bachelor was actually settled in with Preston pre-John Travolta back in 1987. They even lived together and had a potbellied pig together before breaking up in 1989.
Val Kilmer & Cher
The Top Gun star and the legendary diva dated back in the ’80s. She was 14 years his senior.
Seal & Tyra Banks
Before he was Heidi Klum’s ex, he romanced a different supermodel, who was 11 years his junior.
Mark Wahlberg & Jordana Brewster
This former couple stayed way under the radar while dating from 2000 to 2002. How did they pull that off? Brewster told Movieline back in 2001 their secret: “We just know where to go, especially in L.A. If you want to get attention, you know where to go. And if you don’t, you go to more subdued places.”
Meagan Good & Joseph Gordon-Levitt
The duo reportedly started dating after meeting on the set of the 2005 film Brick, but they only stayed together for six months.
Joshua Jackson & Rosario Dawson
The Dawson’s Creek alum and the Josie and the Pussycats star dated for about a year back in 2002.
Chris O’Donnell & Reese Witherspoon
The NCIS: LA stud and America’s sweetheart dated way back in 1993, when 17-year-old Witherspoon first moved to Los Angeles.
Sarah Jessica Parker & Robert Downey Jr.
The man who now rocks the Iron Man suit for Marvel admitted that drugs and alcohol were to blame for the end of his seven-year relationship (1984 – 1991) with the Sex and the City star. “I liked to drink, and I had a drug problem, and that didn’t jibe with Sarah Jessica,” he admitted in an a 2008 interview with Parade, “because it is the furthest thing from what she is. She tried to help me. She was so miffed when I didn’t get my act together.”
Matthew Perry & Heather Graham
The Friends alum and The Hangover star supposedly hooked up in 2003, but their fling didn’t last long enough to be more than a little blip on the Hollywood hookup radar.
Tom Hiddleston & Kat Dennings
The 2 Broke Girls actress dated her Thor costar briefly in 2010, appearing very cozy while attending Comic-Con to promote the Marvel film. But their relationship fizzled by the time the movie premiered the following year.
Cameron Diaz & Justin Timberlake
There was something about their chemistry at the 2003 Nickelodeon Kids’ Choice Awards, where Diaz presented Timberlake with the award for Best Burp—because they dated for almost four years, seriously enough to issue a statement when their relationship ended in 2007, “mutually and as friends, with continued love and respect for one another.”
David Moscow & Kerry Washington
The Scandal star appeared on the cover of InStyle Weddings in 2005 when she was engaged to the Big actor, but they split up in 2007.
Madonna & Tupac Shakur
Madonna never addressed the story that she dated the rapper, who was killed in 1996 when he was only 25, until 2015. When Howard Stern brought up her infamously feisty 1994 chat with David Letterman, she explained, “I was dating Tupac at the time, and the thing is…he got me all riled up on life in general.”
Jake Gyllenhaal & Reese Witherspoon
After her divorce from Ryan Phillippe and before marrying agent Jim Toth, Reese starred with Jake in the 2007 thriller Rendition and they dated for a couple of years.
“She is, as I would say about most of the women who I’m close friends with or had relationships in my life,” Jake said admiringly of his ex, “one of the smartest, strongest people I’ve ever met.”
Meg Tilly & Colin Firth
Before marrying Livia Giuggioli in 1997 (they separated in 2019), Firth had a five-year relationship with Tilly that produced son William Joseph Firth, who was born Sept. 20, 1990. The younger Firth is also an actor who appeared with his father in Bridget Jones’s Baby.
