Gillian Anderson and Peter Morgan
The X-Files alum and Sex Education actress, who played Margaret Thatcher on The Crown, was in a relationship with The Crown creator between 2016 and 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 when he revealed 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 are a pair!
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 pretty settled with Kelly Preston pre-John Travolta back in 1987. They even lived together and had a pet 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
Back in 1996, Heidi Klum's ex-hubby romanced the 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 Fringe star dated Pacey himself 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 in an a 2008 interview with Parade 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, 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," he told the mag.
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 Thor premiered in 2011.
Ryan Reynolds & Kristen Johnson
In 1999, way before he wed Blake Lively, Reynolds dated the 3rd Rock From the Sun star. The duo even attended the premiere of the 1999 film The Green Mile together.
Minka Kelly and Trevor Noah
The Friday Night Lights star and host of The Daily Show dated for about a year. In May 2021, multiple reports said they broke up.
Jake Gyllenhaal & Natalie Portman
These two A-listers dated back in 2006 for a brief time, but they still remain close friends. In 2011, Gyllenhaal poked fun at his ex while presenting Portman with the Desert Palm Achievement Award. "She's a vegan, which makes it really frustrating when you're picking a place to eat," he joked.
Ted Danson & Whoopi Goldberg
This relationship was laced with scandal, as the Cheers actor's affair with his Made in America costar back in 1992 led to his divorce from producer Casey Coates.
Cameron Diaz & Matt Dillon
Diaz and Dillon began dating in 1995, but broke up shortly after they wrapped filming on the 1998 comedy There's Something About Mary.
Julie Bowen & David Spade
Spade's dating roster reads like a who's who of hot Hollywood blonds: Heather Locklear, Nicollette Sheridan and Playboy Playmate Jillian Grace. In 2002, he added the Modern Family star to his list, but the couple called it quits after a year of dating.
Zoë Kravitz & Channing Tatum
After months of speculation, the Pussy Island co-stars all but confirmed they are dating as they rode around New York City on a bicycle.
Renée Zellweger & Ant Anstead
The Judy actress and HGTV star began dating in early June after meeting on the set of the new Discovery+ show Celebrity IOU: Joyride, according to multiple reports. Neither Renée nor Ant have addressed their rumored romance.
Ashton Kutcher & January Jones
Before he was Mr. Demi Moore, Kutcher dated Jones from 1998 to 2001. And according to the Mad Men star, he was not a very good boyfriend. "He was not supportive of my acting," Jones told GQ in 2009. "He was like, 'I don't think you're going to be good at this.' So, f--k you!"