Ben Affleck and Brad Pitt: Gwyneth Paltrow
Our second appearance from Pitt on the list is thanks to the fact that he dated Gwyneth Paltrow, who also dated Ben Affleck. Pitt and Paltrow were together from 1994 to 1997 and were engaged for the last year of their relationship. Affleck and Paltrow were in a relationship on and off from 1997 to 2000.
Colin Farrell and Justin Timberlake: Britney Spears
Everyone remembers that Justin Timberlake and Britney Spears dated—and their iconic matching denim ensembles. But, Spears’ time with Colin Farrell shouldn’t be forgotten, either. This was far from a serious relationship, but the two did attend the premiere of his movie The Recruit together in 2003 while being very flirty.
Nicole Kidman and Cher: Tom Cruise
Sure, you might know that Nicole Kidman and Tom Cruise were married from 1990 to 2001. But, did you know that Cruise also dated Cher? Yes, that Cher. They were together briefly in the ’80s. They met at Madonna and Sean Penn’s wedding and then again while being honored for their achievements as people with dyslexia by Nancy Reagan. What a blast from the past. For more couples from that era, check out 31 Celebrity Couples from the ’80s You’ve Totally Forgotten About.
Matthew McConaughey and Ryan Gosling: Sandra Bullock
Matthew McConaughey and Sandra Bullock dated from 1996 to 1998 after they starred together in A Time to Kill. Then, in 2003, Bullock dated Ryan Gosling, after they starred in Murder by Numbers. She told Cosmopolitan of Gosling, “I live my life at a manic pace, and he’s taught me to disregard all that isn’t important. He’s like a little Buddha.”
January Jones and Demi Moore: Ashton Kutcher
From 1998 to 2001, Ashton Kutcher dated January Jones. Then, four years later in 2005, he married Demi Moore and they were together until a tumultuous split in 2011. Now, Kutcher is married to his That ’70s Show co-star Mila Kunis, and they have two kids together. To see which stars hit it off behind the scenes, check out 50 Celebrity Couples Who Met on Set.
Gisele Bündchen and Blake Lively: Leonardo DiCaprio
Supermodel Gisele Bündchen dated Leonardo DiCaprio from 2000 to 2005 when she decided to make some changes in her life. “Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes,” she wrote in her book Lessons: My Path to a Meaningful Life (via Vogue). Meanwhile, DiCaprio has been known for dating a lot of women, including Gossip Girl star Blake Lively in 2011—a brief relationship that involved a yacht in Cannes. Of course.
Sean “Diddy” Combs and Ben Affleck: Jennifer Lopez
Affleck’s second appearance on the list is for his early ’00s relationship—and 2004 engagement and “Jenny from the Block” music video and terrible movie Gigli—with Jennifer Lopez. Before Affleck, Lopez had another high-profile ’90s relationship when she dated the man then known as Puff Daddy. For more getting-together stories, check out 23 Celebrities Who Married Non-Famous People.
Taylor Swift and Kirsten Dunst: Jake Gyllenhaal
Taylor Swift andKirsten Dunst both dated Jake Gyllenhaal, and both relationships will forever be remembered for two very different reasons. Taylor Swift’s song “All Too Well” was inspired by her 2010 relationship with the actor. As for Dunst, the internet loves to reminisce about that funny photo of her and Gyllenhaal eating lunch in 2003. For more behind-the-scenes drama, check out 16 TV Actors Who Were Replaced Like It Was No Big Deal.
Tyra Banks and Heidi Klum: Seal
Heidi Klum and Seal had been married for seven years when they announced they were splitting up in 2012. But, before their relationship got started, the “Kiss from a Rose” singer dated another model, Tyra Banks, in 1996.
Renée Zellweger and Zoe Saldana: Bradley Cooper
Renée Zellweger and Bradley Cooper dated for about two years from 2009 to 2011 after filming Case 39. Soon after, he started dating Zoe Saldana, with whom he starred in The Words. Saldana and Cooper went on to join the Marvel Cinematic Universe together—they’re both stars of the Guardians of the Galaxy movies.
Jamie Foxx and Tom Cruise: Katie Holmes
Tom Cruise and Katie Holmes had a very fast-paced, very public relationship that started in 2005. They welcomed their daughter Suri and got married in 2006. Six years later, in 2012, Holmes filed for divorce. The next year, rumors began circulating that she was dating Jamie Foxx. Throughout the years, there were many denials and re-ignitions of the rumors, but around 2018, they actually started being seen together in public. In 2019, it was reported that they split up.
Ryan Gosling and Michael Sheen: Rachel McAdams
The Notebook stars Rachel McAdams and Ryan Gosling didn’t get along on set, but they started dating in 2005, the year after the movie came out. The relationship lasted until 2007. McAdams then dated Michael Sheen, who she met when they starred in Midnight in Paris, from 2011 to 2013. They broke up because they had “different visions for the future,” according to what a source told People.
Josh Hartnett and Ryan Reynolds: Scarlett Johansson
Scarlett Johansson and Ryan Reynolds were married from 2008 to 2011. While Johansson said that going through a divorce was tough in an interview with Vogue, she added that theirs was “comically amicable.” Before her marriage to Reynolds, Johansson had been in a relationship with Pearl Harbor star and ’00s teen idol Josh Hartnett around 2006. In an interview with Allure (via People), Johansson, who was 21 at the time, described Harnett as “a good boy. A great person. I’m very lucky and I’m very happy.”
Marlon Brando and Frank Sinatra: Marilyn Monroe
It’s hard to know exactly what went on with any of these extremely legendary people, but it’s been rumored that Marilyn Monroe and Marlon Brando had something going on after her marriage to baseball player Joe DiMaggio, but before her marriage to playwright Arthur Miller. As for Frank Sinatra and Monroe, they’re said to have dated briefly after she split from Miller. Either way, Monroe stayed friends with both actors until her 1962 death.