40 Celebrity Couples You Forgot About

Hollywood is full of surprising relationships, from ill-fated private romances to blink-and-you-miss-it pairings.

by Bustle Editors
Originally Published: 
Jennifer Aniston and Paul Rudd are an example of a surprising celebrity couple.
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It can be hard to keep track of celebrity couples, especially with our lightning-speed news cycle. Obviously, there are couples that break through the noise: the Bennifers, Beckhams, and Eva Mendes and Ryan Goslings of Hollywood.

But in that landscape, lesser-known showbiz relationships can often go unnoticed or forgotten — particularly if they’re short-lived. Do you remember, for example, Madonna and Tupac, Rihanna and Shia LaBeouf, or Mischa Barton and Jamie Dornan?

So, for the sake of some throwback nostalgia, below are 40 of the more surprising celebrity couples from years gone by.

1. Ryan Gosling & Sandra Bullock

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Bullock and Gosling, who were introduced on the set of Murder by Numbers, briefly dated from 2002 until 2003. Despite their 16-year age difference, Bullock tried to avoid Gosling on the Hollywood circuit after their breakup, according to Radar Online. “Sandy’s the type to take things really to heart,” a source claimed. “If anyone hurts her, it’s very hard for her to forgive and forget.”

2. Jessica Biel & Chris Evans

Evans and Biel dated for nearly five years, from 2001 to 2005. They also starred in two films together, Cellular and London, and came close to taking the next step in their relationship. “We both want to be married, and we both want to have children,” Biel told Cosmopolitan in 2005. “But we’re not engaged, so the rumors are false ... so far.”

3. Emma Stone & Kieran Culkin

Before she won Oscars and he won an Emmy, Stone and Culkin were just two up-and-coming actors who fell in love. They started dating on the set of Paper Man in 2010, and while they split a year later, they also made 2013’s Movie 43 together. In an interview with Rolling Stone, Culkin said he doesn’t think of her as an ex: “To me, she’s just a really good friend of mine and my wife’s.”

4. Leighton Meester & Sebastian Stan

While fans shipped Gossip Girl characters Blair Waldorf with Chuck Bass, Meester (who played Blair) was dating a different costar. She and Stan first met in 2007, when he joined the cast as Carter Baizen, and they dated for nearly three years before splitting in 2010.

5. Madonna & Tupac Shakur

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In 1994, two years before Tupac Shakur was fatally shot, the rapper had a fling with Madonna. Speaking on The Howard Stern Show in 2015, she confirmed the ’90s relationship. Referencing a 1994 appearance on The Late Show, she said, “I was dating Tupac Shakur at the time, and the thing is he got me all riled up on life in general.”

6. Julia Roberts & Matthew Perry

Following Roberts’ guest appearance on Friends, she and Perry began dating in real life. In his 2022 memoir, Perry wrote about the courtship. “I sent her three dozen red roses and the card read: ‘The only thing more exciting than the prospect of you doing the show is that I finally have an excuse to send you flowers,’” he wrote. Perry broke it off a couple months later.

7. Rachel McAdams & Michael Sheen

While McAdams and Sheen met in the City of Love while filming Midnight in Paris in 2010, they didn’t start dating until after production wrapped. The pair went public at the 2011 Cannes Film Festival and stayed together for two years before splitting in 2013, reportedly due to McAdams wanting to start a family and Sheen wanting to focus on his career.

8. Cara Delevingne & Ashley Benson

Delevingne and Benson were linked in 2018 but didn’t go public with their relationship for another year. They split in April 2020 while self-quarantining apart.

9. Gisele Bündchen & Leonardo DiCaprio

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DiCaprio’s relationship history is easy fodder for online mockery, but one of his longer relationships was with Bündchen. The pair dated for five years from 2000 to 2005, and despite their shared passions, like basketball and environmentalism, eventually called it quits.

10. Rihanna & Shia LaBeouf

Speaking to Playboy in 2009, the actor revealed that he and RiRi went on one date. “The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends,” LaBeouf said.

11. Cameron Diaz & Alex Rodriguez

Before she married rocker husband Benji Madden, Diaz dated former baseball player Alex Rodriguez. They reportedly got together after meeting at a Super Bowl party in February 2010, and amicably split over a year later. “I have a lot of love for Cameron,” he told People after the breakup. “We’ll always be friends.”

12. Cameron Diaz & Jared Leto

Diaz had a slew of unexpected romances in the early 2000s, including with Leto. They dated for four years starting in 1999, and were rumored to have gotten engaged — which neither of them have confirmed or denied — before eventually splitting in 2003.

13. Nicole Kidman & Lenny Kravitz

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Kidman and Kravitz dated in the early 2000s, per Entertainment Weekly, and were secretly engaged. “I knew Zoe [Kravitz] because I was engaged to her father,” Kidman revealed to The Edit. “It’s all in the family. … I love Lenny. He’s a great guy.”

14. Penelope Cruz & Tom Cruise

Tom Cruise could have been Tom Cruz. He met Penelope Cruz in 2000 on the set of their film Vanilla Sky, but they didn’t start dating for another year. Their relationship lasted nearly three years before ending in early 2004.

15. Penelope Cruz & Matthew McConaughey

After splitting from Cruise, Cruz dated Matthew McConaughey. They met on the set of their 2005 film Sahara, where sparks flew almost immediately. However, they broke up in 2006 due to their “busy work schedules,” which was around the same time that he met his now-wife, Camila Alves.

16. Salma Hayek & Edward Norton

Hayek and Norton were set up by their chiropractor, who reportedly played matchmaker. They quietly dated for three years, and even co-starred in Hayek’s Frida Kahlo biopic.

17. Matthew McConaughey & Janet Jackson

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After meeting at the 2002 Grammys, McConaughey and Jackson struck up a romance. At the time, he claimed they were “just friends,” but as Showbiz Cheat Sheet reported, she later confirmed they were indeed an item. “I guess we did date,” Jackson told Upscale Magazine in 2006. “He is such a great guy and a sweetheart. It was just for a minute, that’s why I’m so hesitant to mention it.”

18. Gwyneth Paltrow & Ben Affleck

Paltrow and Affleck dated on-and-off for three years following her 1997 split from Brad Pitt. For what it’s worth, she’s said that Affleck was “technically excellent” in bed.

19. Reneé Zellweger & Bradley Cooper

Zellweger and Cooper met in 2006 while starring as best friends in the horror film Case 39. When the movie came out three years later, their offscreen connection turned romantic. They kept their relationship so private that many never knew they were dating. They stayed together for roughly two years before calling it quits in 2011.

20. Ciara & Bow Wow

Not only did Ciara and Bow Wow date when they were both 17, when she was an extra in an intro video for his tour. They even got engaged, which he confirmed in 2018. They were together for a few years in the early 2000s, before going their separate ways in 2006.

21. Helen Mirren & Liam Neeson

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In a 2018 appearance on The Graham Norton Show, Mirren and Neeson reminisced about their past romance, which began on the set of 1981’s Excalibur. “We didn’t [just] date. We lived together for four years,” she said. “We were a serious item for a while. Lucky me!” He added, “Before I met her and we worked together, I had read somewhere that if she fancied a guy she would imitate his walk behind his back. And I turned around one day and she was doing that to me.”

22. Mila Kunis & Macaulay Culkin

Kunis and Culkin began dating in 2002 and spent eight years together before splitting in 2011, according to Us Weekly. Speaking to Blackbook in 2009, Kunis expressed that she had little intention of settling down with Culkin, who she was still dating at the time. “It’s just not something that’s important to me,” she said.

23. Jennifer Aniston & Vince Vaughn

Ironically, Aniston and Vaughn started dating while filming The Break-Up in Summer 2005. They were together for a year and a half before splitting in December 2006. At the time, their reps said “they continue to be good friends,” which proved true when Aniston praised him in a 2008 interview with Vogue, saying “he literally brought me back to life.”

24. Alanis Morrissette & Ryan Reynolds

The pair met at Drew Barrymore’s 2002 birthday party and immediately hit it off. They got engaged in 2004, but called it off in 2007, a period that Morissette later referred to as “rock bottom” in an interview with the Los Angeles Times.

25. Angelina Jolie & Billy Bob Thornton

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Jolie and Thornton got married in a small Las Vegas ceremony in 2000, despite the latter being engaged to Laura Dern at the time. They divorced three years later, shortly after Jolie adopted her first child, Maddox. She later attributed their split to having “different paths.” “We just looked at each other one day and we had nothing to say to each other,” she said.

26. Mischa Barton & Jamie Dornan

At the height of Barton’s fame after The OC, she briefly dated Dornan, who was then an up-and-coming actor. As The Daily Mail reported, the pair dated in 2007 and were photographed on several occasions in and around London.

27. Keira Knightley & Jamie Dornan

Knightley met Dornan during his modeling days at a 2003 photoshoot. They dated for two years as Knightley’s acting career was taking off. Dornan later admitting feeling “second-rate” to her, causing tension that led to a 2005 split.

28. Brittany Murphy & Ashton Kutcher

Murphy and Kutcher dated after their 2002 movie, Just Married, when they were working on separate projects. They split in 2003. When Murphy passed away in 2009, Kutcher wrote on X (formerly Twitter), “2day the world lost a little piece of sunshine.”

29. Cher & Tom Cruise

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Back in 2013, Cher confirmed her relationship with Cruise while playing a Watch What Happens Live segment called Truth or Cher. She joked that Cruise “was in the top five” of her past lovers. “It’s not a long list, just a good list. It could have been a great big romance, because I was crazy for him,” she told host Andy Cohen.

30. Sofía Vergara & Tom Cruise

After Cruise split from Cruz, Will Smith set him up with Vergara at his 2005 Oscars party. According to Cruise biographer Andrew Morton, they reportedly broke it off after Vergara wouldn’t renounce her Catholic faith and convert to Scientology.

31. Sofia Coppola & Quentin Tarantino

As if her family didn’t have enough filmmakers, Coppola dated Tarantino in 2003, soon after divorcing director Spike Jonze. They stayed together for two years and have remained friends since — Tarantino even presented her with the Venice Film Festival’s Golden Lion award for 2010’s Somewhere.

32. Kristen Dunst & Jake Gyllenhaal

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Dunst and Gyllenhaal began dating in 2002 after being introduced by Gyllenhaal’s sister, Maggie. According to InStyle, they moved in together and adopted a dog named Atticus before splitting in 2004.

33. Zachary Quinto & Jonathan Groff

Quinto announced his relationship with the Broadway star a few months after coming out. The two split in 2013, which they attributed to long distance, but have remained friends, and even hung out in May 2023.

34. Scarlett Johansson & Jack Antonoff

Johansson and Antonoff were high-school sweethearts, dating from 2001 to 2002 as students at the Professional Children’s School in New York. They even went to prom together and have the cheesy photos to prove it.

35. Jennifer Aniston & Paul Rudd

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According to Cosmopolitan, they reportedly began seeing each other while filming The Object of My Affection in 1998. More than a decade later, in 2012, they appeared to confirm the rumors. “I’ve kissed him for years,” Aniston told GQ when asked if she found it strange kissing Rudd on set. He added, “We’ve made out for decades.”

36. Mandy Moore & Wilmer Valderrama

The That ’70s Show alum dated Moore for two years after meeting at a 2000 photo shoot when she was 15.

37. Kelis & Bill Murray

Kelis’ milkshake brought Murray to the yard for a two-month whirlwind romance. They reportedly started dating after connecting over their late spouses, but had gone separate ways by August 2023.

38. Sarah Jessica Parker & Robert Downey, Jr.

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Parker and Downey Jr. were in a long-term relationship for eight years. Per Cosmopolitan, they met in 1984 on the set of Firstborn. Speaking to Parade in 2008, the Iron Man star revealed how his drink and drug issues led to their separation. “She tried to help me,” he said. “She was so miffed when I didn’t get my act together.”

39. Hilary Duff & Joel Madden

Duff and Madden started dating in 2004 and split two years later. Surprisingly, she and her husband, Matthew Koma, have become good friends with Madden and his wife, Nicole Richie. “We're neighbors, and we actually hang out all the time,” Duff said on Watch What Happens Live in January 2023.

40. Avril Lavigne & Tyga

He was a boy, she was a girl. But no, it wasn’t obvious. The two had an on-and-off romance throughout 2023 but called it off for good in October.

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