11 Celebrity Couples That Were Completely Unexpected

Despite coming from different backgrounds or working in varying parts of the entertainment industry, these famous duos somehow found their way to one another. While these pairings may not have made sense to fans, they clearly had some compatibility…even if they didn’t work out in the end!

Read on to find out which celebrity couples (real and rumored) surprised fans…

1. Bill Murray & Kelis

Rumors recently surfaced that Kelis and Bill Murray had hit it off and were spending a lot of time together. According to TMZ, the 72-year-old actor was spotted at a few of 43-year-old Kelis’ shows in London and they were later seen at the same hotel. The pair are said to be bonding over the recent losses in their life -- Kelis' second husband died in March 2022 and Bill's estranged wife died in 2021.

While the pair haven’t confirmed the dating rumors, Kelis had a coy response when a fan asked if she would "care to address these Bill Murray allegations."

"lol no babe, I wouldn’t bother at all," she wrote on Instagram.

2. Grimes & Elon Musk

Tesla CEO and musician Grimes made headlines when they stepped out at the 2018 Met Gala together. Since then, the pair have had an on-and-off relationship, during which they’ve welcomed two children. In early 2022, Grimes gave some insight into their unique relationship.

"I would probably refer to him as my boyfriend, but we're very fluid. We live in separate houses. We're best friends. We see each other all the time," she told Vanity Fair.

Since then, the pair have called it quits again.

3. Cher & Tom Cruise

In the 1980s, Cher and Tom Cruise had a fling after connecting because they both have dyslexia. Cher says the pair first met when they were invited to the White House for an event but their romance didn’t develop until much later. Looking back, she called Tom one of her "top five" lovers of all time.

"A bunch of people who were dyslexic were invited to the White House, and Tom and I are both dyslexic. We didn't go out till way later, but there definitely was a connection there," she explained, later adding, "Though I don't get what he does, that whole Scientology thing. I can't understand it so I just...don't."

4. Chelsea Handler & 50 Cent

In 2010, Chelsea Handler briefly dated 50 Cent and she now admits that he's one of her favorite ex-boyfriends. After calling him a "big fat teddy bear" on Instagram, Chelsea reflected on their romance while talking to ET Canada.

"Yeah, I guess he’s my favorite ex. I mean, I don’t have a favorite ex. I love 50 Cent, he was fun. He was just a sweetheart and he was fun to be around," she said. "My friends loved hanging out with him. I loved hanging out with him. It was a pretty short-lived romance, it was only two months."

5. Naya Rivera & David Spade

David Spade and the late Naya Rivera had known each for years before they romantically connected. After initially meeting on the set of "8 Simple Rules," they went on to appear in "Mad Families" together. Then in 2017, the pair were spotted getting dinner together and were later photographed getting cozy at a pool in Hawaii. At the time, Naya was 30 and David was 52, making a 22-year age gap between them.

The rumored couple kept the rest of their romance private but reportedly split that June.

6. Courteney Cox & Adam Duritz

Back in the '90s, Counting Crows frontman Adam Duritz dated Courteney Cox. The pair reportedly met when Courteney starred in the Counting Crows' music video for "A Long December" and they hit it off on set. Although Courteney and Adam haven't shared details about their time together, Adam has confirmed that he did date both Courteney and her "Friends" co-star Jennifer Aniston.

"They were nice girls and I went out with them and that was that," Adam told Men's Health.

7. Ben Stiller & Brandi Glanville

Long before Brandi Glanville’s "Real Housewives" days, she briefly dated Ben Stiller. Ben says that back in the '90s, while Brandi was working as a model, the pair had a short fling, although he probably wouldn't call it a relationship.

"It was short-lived and it was fun, I wouldn't characterize it as a relationship. It was a couple of dates and fun. I'm not sure my wife is even aware of that," he said on "Watch What Happens Live."

8. Nicole Kidman & Lenny Kravitz

Although a relationship between Nicole Kidman and Lenny Kravitz may make sense due to their megastar status, their pairing was a little bit unexpected considering Lenny was Nicole's landlord at the time! When they met, Nicole was reportedly subletting Lenny's New York City property. The pair tried to keep the details of their relationship secret and didn't confirm that they had been romantically involved until a decade after things ended. Ultimately, Nicole says it "just wasn't right."

"I wasn’t ready. We weren't ready…I get engaged and I get married -- that’s my thing. I don't want to date. I'm interested in a very, very deep connection," she told Vanity Fair.

9. Ashley Olsen & Lance Armstrong

In 2007, Lance Armstrong was rumored to be dating Ashley Olsen. The pair, who have a 15-year age gap, were spotted together on a few occasions but never confirmed romance rumors. At the time, Lance said he and Ashley were "strictly friends."

Years later, in a biography about the athlete, it was alleged that in the early days of their romance, Lance's friends warned him not to date Ashley because of their age difference. Author Juliet Macur wrote that Livestrong Foundation head John Korioth told Lance, "Whoa, dude, bad idea. You've got to put a stop to this right now," to which Lance allegedly responded, "She's 21…F--k you."

10. Bella Thorne & Scott Disick

Bella Thorne and Scott Disick reportedly dated in 2017, when Bella was 19 and Scott was in his mid 30s. The pair were spotted out on several occasions, but when they headed to Cannes together, Bella says she realized Scott was too much of a partier for her.

"Scott is really nice, sweet, charming. I don’t drink, and he really drinks a lot. And it just ended up ...I just wasn't down. I was like, 'I gotta leave.' We were [at Cannes] a day and a half before I was like I'm booking my flight and leaving. I love to go out and have fun, I love to fucking dance, but I just don't party hardcore like that and it was way too much for me. I was like, 'Woah, this is not the way I live my life, bruh,'" she told Complex.

11. Carmen Electra & Simon Cowell

Carmen Electra first met the notoriously critical Simon Cowell on the set of "Britain's Got Talent." The couple went on to date for nearly six months but things allegedly ended when Carmen found out Simon was also dating Lauren Silverman. While Carmen has never spoken out about the situation, Simon has gone on to welcome two children with Lauren -- and Carmen says she's very happy for him.

"I'm so happy for him. I'm very proud of him and so happy," Carmen told Us Weekly shortly after Simon and Lauren's first pregnancy announcement. "I'm going to call him, like, as soon as I get in the car…I want to know if it's a boy or a girl! It's awesome. I'm super happy for him. He's lovely."