Originally appeared on E! Online
Scrolling through photos of celebrity couples is fun, but delving into who used to be a couple can be downright jaw-dropping.
And now that we’ve come to accept just how many of you weren’t even born yet when some of the famous types we grew up paying $8 to watch at the movie theater—or $4 to watch at home on VHS from Blockbuster (is your mind blown yet?)—were pairing off, let us be the ones to open your eyes to what once was.
From Brad Pitt‘s busy social life before he was engaged to Gwyneth Paltrow (years before he married first wife Jennifer Aniston) to the celebs who were once engaged, cohabitated or just hit a few red carpets in all their dewy glory—as well as the ones who have been exes far longer than they were together but are bonded forever by parenthood—the world is full of stars who found each other for at least a little while.
Let’s just say, going down that road is a real trip.
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So, before you fully check out for the holidays or embark on your long winter’s nap, take a moment to savor a different kind of history. This one is tinged with romance, melancholy, grunge chic and many future Oscar winners, dating hall-of-famers who stepped into the limelight in subtly matching ensembles, some looking like innocent deer braving the wilds of Hollywood.
Jeff Kravitz/FilmMagic
And you’re not seeing double, there are stars who merit multiple appearances on this list, Ryan Reynolds and Alanis Morissette both playing the field before and after they dated in the 1990s before finding their respective forever loves.
So, read on to see all the celebrities who used to date, long before social media was meticulously keeping track of their every move. You oughta know that we’re here to remind you of simpler times:
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?”
Winona Ryder and Matt Damon
It wasn’t just a Gen X fever dream, they really closed out the 20th century as a couple after, legend has it, being introduced by Gwyneth Paltrow (who famously dated Damon’s best bud Ben Affleck). They split up in 2000.
After the fact, Damon called Ryder a “great woman” in a 2004 Playboy interview, while Ryder told Black Book in 2009, “Matt couldn’t be a greater, nicer guy. I’m really lucky that I’m on good terms with him.”
Cameron Diaz and 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.”
Alec Baldwin and Kristin Davis
The most exciting, challenging and significant relationship of all is the one you have with yourself, but Sex and the City alum Kristin Davis still had a good time dating Alec Baldwin when she was starring on the HBO series.
Referencing an old flame who ended things after she loaned him $5,000, Kristin made it clear on a February 2025 episode of the Literally! With Rob Lowe podcast that the mystery man was definitively not the three-time Emmy winner.
“Alec Baldwin was so rich by the time I dated Alec Baldwin,” Kristin shared. “I would have never needed to lend Alec $5,000. Oh my God.”
David Moscow and 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 and 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 and 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.”
Jesse Metcalfe and Scheana Shay
The Vanderpump Rules alum detailed her mid-2000s romance with the Desperate Housewives actor in her 2025 memoir My Good Side.
“We would order in dinner with his parents at his house, and—when we were alone—he would play the guitar and serenade me with songs like ‘Hey There Delilah,’” she wrote. “It felt like I was living a real-life fantasy with this guy I’d watched on TV and in movies for years.”
Meg Tilly and 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.
Mandy Moore and 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 and Alanis Morissette
You oughta know by now that one of the most enduring mysteries in music history is who exactly 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 and Ryan Reynolds
“Oh yeah, I love her music,” Reynolds told People of his then-fiancée in 2005. “It can be awkward when she walks in and I’m listening to it in my underwear dancing.”
The music stopped for the Canadians in 2007, but their breakup after four years together was very polite.
January Jones and Jason Sudeikis
Minnie Driver and 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 and Liam Neeson
The stars met on the set of the 1981 movie Excalibur and eventually lived together (Neeson says Mirren gave him his first driving lessons) before they broke up in the mid-’80s.
“I should be so lucky and be honored to have spent three or four years with that lady,” Neeson told ET Canada in February 2023. “She’s really something else.”
Jeff Goldblum and Laura Dern
Finding love in Jurassic Park? What a meat cute.
The co-stars began dating 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.”
They got engaged in 1995 but ultimately split two years later. They reunited on-screen for the first time in 2022’s 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. Anderson won an Emmy for her turn as 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 and 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 and 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 and 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 and George Clooney
The famous bachelor was actually settled in with Preston pre-John Travolta back in 1987. They even lived together and shared a potbellied pig named Max before breaking up in 1989.
Val Kilmer and Cher
Why, yes, she does believe in life after love. The late Top Gun star and the legendary diva dated back in the ’80s following her divorces from Sonny Bono and Gregg Allman.
Seal and Tyra Banks
Before he was Heidi Klum‘s ex, the “Kiss from a Rose” musician romanced a different supermodel.
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‘ The preceding article may include information circulated by third parties ’
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