Gwyneth Paltrow Makes Rare Comment About Past Ben Affleck Romance

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

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

Madonna and Tupac Shakur

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

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

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

You can't blame the Mad Men star for liking funny guys. Jones and Sudeikis dated for a few months in 2010, five years before she briefly dated Will Forte.

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.

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

Regina King and Malcolm-Jamal Warner

Kelly Preston and George Clooney

Val Kilmer and Cher

Seal and Tyra Banks

Meagan Good and Joseph Gordon-Levitt

Joshua Jackson and Rosario Dawson

Chris O'Donnell and Reese Witherspoon

Sarah Jessica Parker and Robert Downey Jr.

Matthew Perry and Heather Graham

Tom Hiddleston and Kat Dennings