If you’re interested in the personal lives of celebrities from the past and present, this is the list for you. There are Old Hollywood scandals, such as the one that led Elizabeth Taylor from her third to her fourth to her fifth husband. There are teen love triangles, like the one that existed between Aaron Carter and two of young Hollywood’s biggest stars. And there are forgotten flings of the past, like the one between a Sex and the City star and the most eligible bachelor, like, ever, and the one between Tom Cruise and… Cher? Yeah, that happened and it involved Nancy Reagan and Madonna. Do I have you intrigued yet? Read on for 35 pairs of celebrities who share an ex and some of the surprising stories of their romances and eventual breakups. RELATED: 28 Celebrities Who Married Normal, Non-Famous People. As you may have noticed from their extremely loved-up Instagram posts, Blink-182 drummer Travis Barker and Kourtney Kardashian are dating. But, prior to those two getting together, there were rumors that Barker and Kim Kardashian had a fling. His ex-wife, Shanna Moakler, has even claimed that she had “caught” the pair together while they were still married. Kim denied Moaker’s accusation, calling it a “false narrative.” Taylor Swift and Harry Styles dated very briefly circa 2012, an extremely public relationship that he later called “a learning experience.” The former One Direction singer is now seeing Olivia Wilde, who directed him in the upcoming movie, Don’t Worry Darling. They made their couple debut at a wedding in early 2021. Former co-stars Courteney Cox and Jennifer Aniston are friends through thick and thin. Not even seeing the same guy could rupture their relationship. Aniston was the first Friend to date Counting Crows frontman Adam Duritz, in 1995. Two years later, he and Cox got close when she appeared in the band’s video for “A Long December.” Only the relationship between Aniston and Cox lasted—they’re still BFFs today. RELATED: ’90s Celebrity Couples You Totally Forgot About. Emma Roberts and Magic Mike star Alex Pettyfer were an item from 2007 to 2008, but that relatively short romance had nothing on Roberts’ rollercoaster relationship with American Horror Story star Evan Peters. The two actors were off and on from 2012 to 2019, and even engaged for part of that time. Roberts ended up moving on with Garrett Hedlund, with whom she just welcomed her first child. The Vampire Diaries co-stars Nina Dobrev and Ian Somerhalder had chemistry on and off screen. They dated from 2010 to 2013, and continued to work together after their breakup. A year later, he started dating Twilight star Nikki Reed. They were engaged six months after their romance began and have since gotten married and had a daughter. In a 2019 appearance on Watch What Happens Live (via People), Dobrev answered a fan who asked if it was “weird” to still be friends with her ex and his wife. ““Why can’t everyone be friends?” the actor said. “I think they have a beautiful baby, and they are happy and so am I. What’s bad about that? I don’t see any problem with that.” Jennifer Aniston and Brad Pitt were married from 2000 to 2005. Juliette Lewis and Pitt were together a decade earlier, from 1989 to 1993. What? Did you think we were going to talk about somebody else? Back in the early ’00s, Aaron Carter dated both Hilary Duff and Lindsay Lohan. “I started dating Hilary on my 13th birthday,” he told CNBC in 2005 (via Us Weekly). “I was dating her for like a year-and-a-half and then I just got a little bored so I went and I started getting to know Lindsay, dating Lindsay.” Seems about right for a famous teenager. Taking things back to Old Hollywood, actors Debbie Reynolds and Eddie Fisher were married for four years in the ’50s and welcomed children Todd Fisher and Carrie Fisher. But, in 1959, Fisher left Reynolds for Elizabeth Taylor. Taylor and Reynolds had been friends, as had Fisher and Taylor’s former husband, Mike Todd, who died in a plane crash a year earlier. Fisher was number four on Taylor’s list of seven husbands. She left him for Richard Burton. 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. 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.ae0fcc31ae342fd3a1346ebb1f342fcb 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. 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.” From 1998 to 2001, Ashton Kutcher dated January Jones. Four years later, 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. 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. 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 celebrity news sent right to your inbox, sign up for our daily newsletter. Taylor Swift and Kirsten 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. 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 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. Becoming teen idols, being pursued by paparazzi, and starring in a huge movie franchise sounds stressful, so it’s no wonder Robert Pattinson and Kristen Stewart bonded over their Twilight experience during their four-year relationship, which ended in 2013. Their careers later led them to indie movies… and indie music singers. Stewart dated musician St. Vincent (aka Annie Clark) in 2016. And Pattinson moved on to FKA Twigs. Sarah Jessica Parker has been married to Matthew Broderick for over 20 years now, but before they got together, she dated two other famous faces. Parker and Robert Downey Jr. started dating in 1984 when they were only 18 years old, and they stayed together for seven years. Soon after, the Sex and the City star dated John F. Kennedy Jr. for several months. Way before he was Captain America, Chris Evans dated Jessica Biel from 2001 to 2006. They even were considering getting married. Fast forward through a long list of rumored relationships, and in 2016, Evans started dating actor and comedian Jenny Slate on-and-off until 2018. Rashida Jones and John Krasinski’s characters were in a relationship on The Office, and they had actually dated in real life before filming together. She also appeared in his film Brief Interviews with Hideous Men. Before that, Jones was with Tobey Maguire—the silver screen’s first Spider-Man—from 1997 to 2000. One of the great mysteries of our time is whether Alanis Morissette’s hit “You Oughta Know” is really about Uncle Joey from Full House. That’s because Morissette dated Dave Coulier in the early ’90s. The singer went on to date fellow Canadian Ryan Reynolds. They got engaged in 2004, but ended their relationship in 2007. Well, this one is interesting. Laura Dern and Angelina Jolie both have Billy Bob Thornton as an ex, because Thornton married Jolie while he was still engaged to Dern. “I left our home to work on a movie, and while I was away, my boyfriend got married, and I’ve never heard from him again,” Dern told Talk magazine in 2000 (via ABC News). Jolie and Thornton divorced in 2003. 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 Cruise’s Collateral co-star 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. Kate Hudson and Alex Rodriguez dated briefly in 2009, with their most notable moments being that she attended a bunch of Yankees games to support him. Then, in 2011, the baseball player dated Cameron Diaz, with their most notable moment being that she fed him popcorn at the Super Bowl. Lenny Kravitz and Lisa Bonet were an It couple of the late ’80s, and welcomed their daughter, actor Zoe Kravitz, together before their split in 1991. Kravitz went on to get engaged to Nicole Kidman, who he was with from 2002 to 2003. Everyone is still friends. 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. 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. And now for Affleck’s third appearance on the list. Affleck and Jennifer Garner got married in 2005 and had three kids together. They broke up 10 years later, in 2015. But before Garner was half of Bennifer 2.0, she was married to her Felicity co-star Scott Foley from 2000 to 2003. Former NFL player Tony Romo dated both Carrie Underwood and Jessica Simpson… and it appears neither relationship ended well. Underwood, who dated Romo in 2007, called him “a guy that did me wrong” in an interview with Esquire. Jessica Simpson dated Romo from 2007 to 2009. She wrote in her recent memoir that they broke up because Romo thought she cheated on him with singer-songwriter John Mayer, with whom she had an on-and-off relationship. In 2014, Fast and Furious franchise star Michelle Rodriguez and model and actress Cara Delevingne had a rowdy time at a New York Knicks game. They dated for a few months before splitting up. More recently, Delevingne dated Pretty Little Liars star Ashley Benson for two years before they broke up in May 2020. Back in 1991, Julia Roberts was engaged to marry 24 actor Kiefer Sutherland, but called off the wedding three days before it was set to happen and ran off with his friend and Lost Boys co-star Jason Patric. Two years later, that was over and Roberts married country singer Lyle Lovett. They were together until 1995. Reese Witherspoon and Ryan Phillippe got married in 1999, after meeting at her 21st birthday party two years earlier and starring in Cruel Intentions together. They had two children together—who look just like them—and divorced in 2007. Soon after, Witherspoon met Jake Gyllenhaal on the set of the film Rendition and they dated until 2009. 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.” RELATED: See 15 Celebrity Couples on Their First Red Carpet Together.
