Jamie Foxx and Katie Holmes
Despite keeping their six-year relationship on the down low, Foxx and Holmes were spotted a few times in public together before they called it quits. For example, in May 2018, shortly before their breakup, they arrived separately for the pre-Grammys gala and sat at a table together. They made their only public appearance as a couple at the 2019 Met Gala.
Justin Timberlake and Jenna Dewan
Singer Justin Timberlake and actress Jenna Dewan once dated in secret. The two met while she was working as one of his backup dancers back in 2003. In an interview on Watch What Happens Live with Andy Cohen, Dewan confirmed that after his big breakup from Britney Spears, they were briefly together.
Ryan Gosling and Sandra Bullock
Ryan Gosling’s been in the public eye ever since his breakout role in The Notebook, but you may not know that he dated Sandra Bullock for a year and a half before they split in 2003. Gosling revealed the reason why their relationship didn’t work out, which he blamed on the entertainment industry and Hollywood.
Michael Jackson and Madonna
We all know that Madonna is an icon, but have you ever wondered just how much of an icon she really is? Well, the pop star recently revealed a piece of juicy pop culture trivia that we never could’ve guessed – that she once had a fling with Michael Jackson. As far as pop culture history goes, this is a pretty big revelation.
Bradley Cooper and Renee Zellweger
It might surprise you to know that actors Bradley Cooper and Renee Zellweger had a thing back in the day. The two met while filming Case 39 together back in 2006. Their two-year romance started in 2008, and they kept it under wraps. He split with her in 2011 due to his busy schedule.
Drew Barrymore and David Arquette
David recently revealed that he used to date Drew Barrymore, calling the actress “one of the sweetest, kindest people in Hollywood.” Apparently, David and Drew only dated for a short time and have remained friends. They’ve even worked together on the movies Never Been Kissed and Scream.
Seal and Tyra Banks
Heidi Klum may have been Seal’s first wife, but she was not the crooner’s first supermodel. In fact, he was previously linked to another model: Tyra Banks. The supermodel and the singer-songwriter dated briefly in 1996, but the pair broke up shortly after and kept their romance out of the headlines.
Sarah Jessica Parker and Robert Downey Jr.
It might surprise you to know that Sarah Jessica Parker and Robert Downey. Jr dated for seven years. The future Iron Man star and future Carrie Bradshaw dated from 1984 to 1991. During this time the actor was battling his substance abuse demons, which eventually led to the end of their relationship.
Cameron Diaz and Robbie Williams
Who would have thought that a British pop singer could charm the pants off an American actress? Well, he did, and while it’s hard to believe that this unlikely pairing actually happened, their fling was really quite short-lived. The romance ended just as suddenly as it began, but it was definitely a memorable summer for both parties involved.
Winona Ryder and Matt Damon
Winona Ryder and Matt Damon were an item for about two years in 2000. Damon had previously dated his Good Will Hunting co-star Minnie Driver, and in the aftermath of their split both Damon and Ryder have avoided dating other celebrities. Ryder has since said her ex “couldn’t be a greater, nicer guy. I’m really lucky that I’m on good terms with him.”
Vanessa Hudgens and Josh Hutcherson
Josh Hutcherson revealed that he and actress Vanessa Hudgens had a secret relationship after meeting on the set of the 2012 film Journey 2: The Mysterious Island, but that it didn’t end well. Soon after their breakup, Hudgens went on to have an eight-year relationship with Austin Butler, and Hutcherson began dating his current girlfriend, Claudia Traisac.
Kim Kardashian and Nick Lachey
Kim Kardashian has had her fair share of high-profile relationships, but one famous ex you might not have heard about is Nick Lachey. They were an item in 2002, and Nick revealed that Kim was so obsessed with fame that she would frequently call the paparazzi on them. Apparently, he wasn’t too fond of her pursuit of celebrity status and their relationship ended pretty quickly.
Kristen Bell and Matthew Morrison
When she was still just a struggling actress, Kristen Bell met Matthew Morrison at college. The two dated briefly but broke up to focus on their careers. It wasn’t until years later that Bell found herself as the star of Veronica Mars and Morrison was becoming an international sensation on Glee. Morrison has since wed Renee Puente, while Bell married Dax Shephard.
Brad Pitt and Sinitta
Back in the 1980s, when Brad Pitt was just starting his career as an actor, he dated singer Sinitta (who was a pop star at the time). However, their relationship didn’t last because they lived too far apart from each other and found it too difficult to maintain a relationship due to the long distance.
Amanda Seyfried and Alex Skarsgård
In an interview with Elle, actress Amanda Seyfried confirmed that she had dated Alexander Skarsgard, who is best known for his role as Eric Northman in the HBO vampire series True Blood. She also said they’d broken up because she was still in love with her Mamma Mia co-star Dominic Cooper. “He’s super funny,” Amanda told the magazine, “but I was too involved with Dom.”
Helen Mirren and Liam Neeson
Liam Neeson and Helen Mirren met while filming the 1981 sword-and-sorcery flick Excalibur and started dating shortly thereafter. It was all very romantic, but unfortunately, that love was short-lived. “To be honest, it was difficult to let go,” Mirren said in an interview. Despite their five-year relationship, the two remain friends to this day.
Ryan Reynolds and Alanis Morrisette
We sometimes forget that even celebrities have a past. Like most of us, Ryan Reynolds has had his fair share of relationships, including with singer Alanis Morrisette. Reynolds started dating Alanis in 2002 before they got engaged in 2004. They met at a party hosted by actress Drew Barrymore. But sadly, there was no wedding to follow – the pair separated in 2007.
Ashton Kutcher and January Jones
In 1998, Ashton was just getting his big break on a sitcom called That ’70s Show. Meanwhile, future Mad Men star January was trying to make it as an actress. But while she was building up her resume, her then-boyfriend, Kutcher, told Jones that she shouldn’t pursue her acting dreams as he didn’t believe she was good enough. Yikes. No wonder they broke up.
Kylie Minogue and Lenny Kravitz
Kylie Minogue and Lenny Kravitz are both music royalty, but the pair also enjoyed a brief romance in 1991. Not much is known about their relationship or why they broke up, but the fling began after Minogue split from the late INXS front man Michael Hutchence earlier that year.
Keira Knightley and Jamie Dornan
There’s no denying the fact that it’s hard for any actor to date another actor, and things can get tricky when one half of a couple is more successful than the other. This was exactly what happened to Jamie Dornan when he started dating actress Keira Knightley in 2003. They broke up in 2005 due to his insecurity about her status compared to his own.
Jennifer Lopez and Sean Combs
When Jennifer Lopez and Sean Combs (then known as Puff Daddy) started dating in 1998, it seemed like a match made in tabloid heaven. She had just ascended to superstardom as an actress and singer, while was a successful rapper as well as an actor, record producer, and fashion mogul. But 18 months into their relationship, they broke up due to his alleged infidelity.
Matthew McConaughy and Janet Jackson
We know it’s hard to believe, but Matthew McConaughy and Janet Jackson were an item…sort of. The two met at the Grammys in 2002, and the actor called the singer a ‘sweetheart.’ Jackson later confirmed their brief relationship, stating that ‘it was just for a minute’, but he was a ‘great guy.’
Mila Kunis and Macauley Culkin
So, here’s something you might not have known about Mila Kunis: before she and Ashton Kutcher got married in 2015, Mila and Macaulay Culkin were a couple for nine years. Nine years! That’s a really long time, especially considering they met so young – when Mila was 18 and the Home Alone icon was 21.
Rachel McAdams and Michael Sheen
American actress Rachel McAdams and British actor Michael Sheen met in 2010 on the set of the Woody Allen film Midnight in Paris and debuted their romance at the 2011 Cannes Film Festival. The couple were together for three years but broke up in 2013.
Zachary Quinto and Jonathan Groff
In an interview with Out Magazine in 2012, Heroes/Star Trek actor Zachary Quinto confirmed that he and actor Jonathan Groff (Frozen, The Matrix Resurrections) were dating. “I’m incredibly happy, I’m incredibly lucky,” said Quinto. The two dated for one year, but ultimately ended their relationship in 2013 due to struggles with long distance.
Cindy Crawford and Richard Gere
Cindy Crawford was arguably the world’s most famous model when she met actor Richard Gere in 1988 at a barbecue at the home of their mutual friend. They dated for four years before getting married in 1991. The marriage would last only four years, though, as the couple separated in 1995 and finalized their divorce later that year.
Cher and Tom Cruise
When Tom Cruise first started in the movie industry, he dreamed of becoming a big Hollywood star. However, Cruise’s career was just starting to blossom when he met Cher, then at the height of her fame. On an episode of Watch What Happens Live with Andy Cohen, the singer confirmed that she briefly dated the Mission: Impossible star in 1985.
Cameron Diaz and Jared Leto
Cameron Diaz has been linked to a number of celebrities over the years, including Justin Timberlake and Matt Dillon. However, one of her longest relationships was with actor Jared Leto – and they kept their romance under wraps for quite a while. They were also spotted at various events together around Hollywood until 2003 when their relationship came to an end.
Gwyneth Paltrow and Luke Wilson
Oscar-winning actress Gwyneth Paltrow famously had high profile relationships with Brad Pitt, Ben Affleck and Coldplay’s Chris Martin, but did you know that she also dated Luke Wilson? Paltrow and Wilson were reportedly an item for a year after they co-starred in The Royal Tenenbaums.
Rashida Jones and John Krasinski
Rashida Jones and John Krasinski dated for almost a year in the mid-2000s, but when Rashida came on to play Jim’s love interest, Karen, on The Office, they had already broken up. But that didn’t stop the two from having great chemistry on screen. Jones is now in a long-term relationship with Vampire Weekend frontman Ezra Koenig, whilst Krasinski is married to Emily Blunt.
Cara Delevingne and Michelle Rodriguez
Model and actress Cara Delevigne and Fast & Furious star Michelle Rodriguez were an item for a hot second in 2014, but it seems like things didn’t last too long before they parted ways. The two of them got together at the beginning of the year and called it quits at the end of May.
Emma Stone and Kieran Culkin
In 2009, Emma Stone starred in Paper Man, a quirky comedy along the lines of Napoleon Dynamite, in which she co-starred alongside Kieran Culkin. The couple started dating in 2010 and dated for about one year. They were last seen together in 2011, after which they broke up.
Julie Bowen and David Spade
David Spade is best known for his comedic roles, but he was also pretty popular in the dating scene in the ’90s and early 2000s. Spade famously dated Heather Locklear and Nicollete Sheridan. But here’s something you might not know: Spade also dated Modern Family star Julie Bowen from 2002 to 2003.
Nicole Kidman and Lenny Kravitz
Nicole Kidman shocked the world in 2018 when she revealed that she had once been engaged to the father of her Big Little Lies co-star Zoe Kravitz, Lenny Kravitz. The pair split in 2003 and Nicole Kidman is now happily married to Keith Urban. Details of the relationship have not been revealed, but Zoe shared how Kidman has always been ‘so nice’ Kidman to her.
Joaquin Phoenix and Liv Tyler
Although they didn’t end up staying together, Liv Tyler and Joaquin Phoenix stayed friends after their 1996 breakup. The two had dated for three years when they were only 18 and 20, but Tyler told Elle that she’s still “friends with all my exes! I love them so much!”
Brooke Shields and Nicolas Cage
Not much is known about the love life of Brooke Shields and Nicolas Cage, other than the fact that they had one. The two were linked in 1987 when they were spotted together at the premiere of Cage’s film Moonstruck. It’s not clear how long their brief relationship lasted past that date.
Kim Kardashian and Nick Cannon
Do you remember when Kim Kardashian and Nick Cannon dated? Yes, that was a thing. It was back in the 2000s, and their relationship was so short it may as well have never existed. They dated for less than a year, from late 2006 to 2007, and allegedly split due to Kim’s sex tape, which leaked in 2007.
Emily Blunt and Michael Bublé
Though they’re now happily married to other people, actress Emily Blunt and singer Michael Bublé dated for three years, from 2005 to 2008, even though this managed to escape the attention of most of us. The couple were rumoured to have broken up due to Bublé’s infidelity, but he has denied those claims.
Elon Musk and Talulah Riley
There are a lot of strange celebrity relationships out there, but this one might be the oddest of them all. Actress Tallulah Riley and tech billionaire Elon Musk started dating in 2008. Riley was 23 at the time and Musk was 37. They got married in 2010, divorced in 2012, remarried in 2013, and then got divorced again in 2016. But this odd pairing has been largely forgotten by the public.
Emilia Clarke and Seth McFarlane
While Emilia Clarke is best known for her role as Daenerys Targaryen on Game of Thrones, she also dated Seth MacFarlane for a while. The relationship only lasted for a year, from 2012 to 2013. The two broke up due to long distance, and potentially the large age gap (MacFarlane was 39 at the time whilst Clarke was 26).
