Everyone has at least one relationship they look back on and ask, “What in the world was I thinking?” These momentary lapses in judgment are a rite of passage, heck, even celebrities are guilty of playing fast and loose with their hearts.
Hollywood relationships may seem like revolving doors, yet these mismatched celebrity pairs got together long enough to leave most of us scratching our heads. But while some of these couples fizzled out as quickly as they began, others continue to prove that there really is someone for everyone — no matter what other people say.
1. Angelina Jolie & Billy Bob Thornton: From their intense PDA to wearing vials of each other’s blood around their necks, Jolie’s three-year marriage to Thornton was like candy to the entertainment media. The pair was even set to adopt a child before their relationship ended abruptly in 2003.
2. Pete Davidson & Kate Beckinsale: Fresh off his breakup with pop star Ariana Grande, the SNL funnyman turned heads after he was spotted cozying up with the 45-year-old actress in early 2019. Their whirlwind romance lasted four months, though some fans still can’t believe it even happened.
3. Hugh Hefner & Crystal Harris: The Playboy Mansion was no stranger to beautiful women roaming its halls, though in 2012, Hef decided to turn his love palace into a love nest when he wed the 23-year-old Harris. The couple remained married until Hefner’s death in 2017.
4. Mary-Kate Olsen & Olivier Sarkozy: Even with their 17-year age gap, Olsen fell head-over-heels for the French banker way back in 2012. The couple wed in 2015 after a three-year courtship, making the 33-year-old fashion designer stepmother to Sarkozy’s two teenage children.
5. Michael Jackson & Brooke Shields: Despite the platonic nature of their relationship, Jackson called Shields “one of the loves of my life” and even discussed marriage with her. However, the two gradually grew apart — they hadn’t seen each other in 16 years upon Jackson’s death in 2009.
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6. Sandra Bullock & Jesse James: What was “America’s sweetheart” doing with a motorcycle bad boy? That was everyone’s thought when Bullock and James wed in 2005. Unfortunately, a series of infidelities on James’ part led to a messy divorce for the couple in 2010.
7. Tom Cruise & Cher: Evidently, Cher did believe in life after love after all. The iconic singer dated a laundry list of famous men following her split with Sonny Bono including Cruise, whom she called one of her “best lovers.”
8. Chelsea Handler & 50 Cent: What started as a bit of harmless flirting on her talk show became a hot and heavy fling between Handler and the rap legend in 2010. Though the pair split after only a few months, they still remain friendly.
9. Carmen Electra & Dennis Rodman: After wedding in Vegas in 1998 Rodman filed for an annulment nine days later, claiming he was of “unsound mind” when he married Electra. Though the pair eventually reconciled, they wound up divorcing four months later.
10. Katy Perry & Russell Brand: What seemed like a marriage built to last ended after just 14 months, as conflicting schedules and Perry’s desire to not rush into having children drove them apart. Brand apparently never spoke to Perry again after texting that he was divorcing her.
11. Sacha Baron Cohen & Isla Fisher: A couple since 2002, Baron Cohen and Fisher didn’t marry until she converted to Judaism in 2010. The couple has three children together, whom Fisher says sometimes get confused when Baron Cohen slips into one of his characters.
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12. Kat Dennings & Josh Groban: While you might think it was the charming tenor’s sultry vocals that drew her in, Dennings admitted that it was Groban’s witty tweets that made her fall for him in 2014. They dated for almost two years before mutually parting ways in 2016.
13. Avril Lavigne & Chad Kroeger: When two Canadian music stars get together to collaborate, love is bound to blossom. Lavigne and Kroeger married in 2013 just a year after the two began writing music, though in 2015, they announced their split.
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14. Pamela Anderson & Kid Rock: After calling off their two-year relationship in 2003, Anderson and Kid Rock reunited in 2006 and were married for just under a year. Many believe Anderson’s infamous appearance in Borat was the final blow to their marriage.
15. Cory Booker & Rosario Dawson: Alongside those for his presidential campaign, Booker made headlines when word got around that he was actively dating the Hollywood actress. Though First Lady Rosario Dawson doesn’t seem to be in the cards, she and Booker still seem to be going strong.
16. Renée Zellweger & Kenny Chesney: Despite all signs pointing to great marriage, Zellweger filed to have their union annulled just four months after their May 2005 wedding. Citing “fraud” as the reason, the couple later clarified that their respective marriage goals hadn’t been clear when they wed.
17. Ashton Kutcher & Demi Moore: Even with 16 years separating them, Moore had “never been so happy” when she and Kutcher wed in 2005. However, Kutcher’s infidelities became too much to overlook, and Moore filed for divorce in 2011.
18. Kerry Washington & Nnamdi Asomugha: It’s not often that two worlds collide, though that’s exactly what happened when the Hollywood heavyweight wed the former NFL All-Pro in 2013. It seems Washington has already rubbed off on her hubby, as Asomugha is now pursuing an acting career of his own.
19. Sean Penn & Madonna: After wedding on her birthday in 1985, Penn and Madonna starred in 1986’s Shanghai Surprise together, and the singer’s third album, True Blue (1986), was dedicated to Penn. The good feelings wouldn’t last, however, and the couple divorced in 1989.
20. Julie Bowen & David Spade: The Modern Family star and career comedian seemed quite the mismatched pair even back when they were a couple in 2002. They dated for just a year before deciding to call it quits.
21. Oprah Winfrey and Stedman Graham: These two met at a charity event in 1986, and they’ve continued their romance ever since. She’s worth quite a bit more than him, but no one can put a price on their love!
22. Joaquin Phoenix and Rooney Mara: This couple tends to shy away from the limelight, which is probably why they work. They met on the set of Her, and while they’re not married, one day all that could very well change…
23. Natalia Dyer and Charlie Heaton: These two actors met on the set of Netflix’s Stranger Things, and fell for each other quickly. Their feelings definitely gave their onscreen chemistry a realism that’s hard to fake!
24. Benji Madden and Cameron Diaz: This duo tries not to let people into their private lives, but they’re totally head over heels for each other. Madden is in the band Good Charlotte, and Diaz, who has retired from acting, now has plenty of time to go to his shows.
25. Aaron Taylor-Johnson and Sam Taylor-Wood: Despite the 24-year age gap, the two wed in 2012 when Taylor-Johnson was just 19. After meeting on the set of the movie Nowhere Boy, the couple knew they wanted to be together for the long haul.
26. David Cross and Amber Tamblyn: This couple has a 19-year age gap between them, but it sure doesn’t get in the way of their love either. They actually met at an airport and bonded over an issue of Sky Mall magazine!
27. Geoffrey Arend and Christina Hendricks: Hendricks has said that the moment she met Arend, she fell for him. They were introduced on the set of Mad Men, and she was immediately drawn to him. Two years later, they were married.
28. Francois-Henri Pinault and Salma Hayek: Oscar winner Hayek married this French billionaire in 2007, and they have one daughter together. Hayek said her biggest accomplishment in life was creating a marriage full of love.
29. Adam Shulman and Anne Hathaway: The actress and jewelry designer met in 2008 at the Palms Springs Film Festival. Hathaway said Shulman’s “unique and specific love changed me.” How sweet!
30. Keira Knightley and James Righton: This couple hit it off and then made it legal in 2013. Knightley hadn’t heard her soon-to-be-husband’s rock music at the time, but she quickly became a mega fan.
31. Lisa Kudrow and Michel Stern: This couple wed in 1995, and they’ve held strong ever since. Before the French marketer got together with Kudrow, he was actually in a relationship with her roommate!
32. Meryl Streep and Don Gummer: Streep is one of the greatest actresses of all time, and she puts just as much effort into her marriage with sculptor Don Gummer; they’ve been together for over 40 years! She has described him as the “linchpin” of her life.
33. Jeff Richmond and Tina Fey: This couple met while working at The Second City improv theater in Chicago. They eventually moved onto Saturday Night Live together, as well. There’s no shortage of funny in their household!
34. Dan Baldwin and Holly Willoughby: They’ve both admitted it wasn’t a love-at-first-sight situation. However, they’ve been married since 2007, and have three children! It doesn’t look like their happiness is dwindling.
35. Andrew Upton and Cate Blanchett: When this actress and director first met, sparks didn’t fly. She thought he was arrogant! However, after they played a game of poker together, Blanchett claims he stole her heart.