Hollywood can bring some pretty unlikely pairs together. Case in point? These famous match-ups, featuring a wide range of actors, musicians, and athletes, were so under-the-radar that you probably never even heard about them.
Below, check out 15 unexpected celebrity flings that you likely didn’t know about:
1. Natalie Portman and Moby
Talk about an odd couple! Natalie Portman and musician Moby reportedly dated briefly way back when, although the exact timing of their relationship is still unclear.
Moby himself confirmed their romance in 2008, saying that the short fling made him a hated man among certain fan groups. “As far as the very brief affair that I had with Natalie, it’s made me a target of a lot of nerd wrath,” he said, per Page Six. “You don’t date Luke Skywalker’s mom and not have them hate your guts.”
2. LeAnn Rimes and Tiger Woods
Before LeAnn Rimes married her first husband, Dean Sheremet, in 2002, the singer actually dated the famous golfer. According to Us Weekly, the unlikely pair went out several times and were having a good time — until her father interfered.
That’s right. Rimes’ dad was apparently not too thrilled about his teen daughter dating the older athlete (who is seven years her senior) and made her stop seeing him. That wasn’t the end of their relationship troubles though. Both stars later went on to have highly publicized affairs in their respective marriages.
3. Conan O’Brien and Lisa Kudrow
Before nabbing her breakthrough role as Phoebe on Friends, Lisa Kudrow had a short-lived relationship with fellow TV star, Conan O’Brien. “He was really smart, really funny, and he thought I was funny,” Kudrow said of the match-up in 2011.
So why did it end? According to the actress, the pair eventually found they “were better as friends.”
4. Ashton Kutcher and January Jones
January Jones had just moved to Los Angeles when she met the then up-and-comer, Ashton Kutcher. The two began dating in 1998 and continued their relationship for several years, before eventually breaking up in 2001.
Jones later sparked speculation that Kutcher wasn’t exactly the best boyfriend to her. “The guy I was dating when I first got to L.A. was not supportive of my acting,” she told GQ in 2009, although she later clarified that she never specifically mentioned Kutcher by name.
5. Madonna and Dennis Rodman
The famous musician enjoyed a very public two-month fling with the former NBA player in 1994. Dennis Rodman later wrote about their relationship in his book, Bad As I Wanna Be, even suggesting that the artist wanted to have a baby with him.
“Madonna talked all the time about having a baby. I think she wanted every bit of Dennis Rodman–marriage, kids, everything,” he wrote, per the Chicago Tribune. He also claimed that while the two felt like “soul mates,” they eventually broke up because he felt her fame would overwhelm his identity.
6. Kristen Bell and Matthew Morrison
These two TV stars dated for a short period back in their college days at New York University. “I actually went to college with Matty Morrison,” Kristen Bell told Us Weekly in 2010. “We actually dated very briefly.”
Bell is now married and shares two kids with fellow actor Dax Shepard. Meanwhile, Matthew Morrison was linked to several more Hollywood stars, including Glee costar Lea Michele, before settling down with wife Renee Puente.
7. Seth MacFarlane and Emilia Clarke
The brains behind Family Guy and Khaleesi, the Mother of Dragons herself? That’s one pairing that no one would have ever expected, but Seth MacFarlane and Emilia Clarke apparently hit it off upon meeting in 2012.
The actors dated long-distance for several months, while Clarke was busy shooting Game of Thrones in Europe and MacFarlane worked out of California. They eventually called it quits in 2013, due to the distance and their busy schedules.
8. Sofia Vergara and Enrique Iglesias
It’s hard to believe now, but there was once a time when Sofia Vergara was mostly known stateside for being Enrique Iglesias’ ex. According to People, Vergara and Iglesias dated sometime before the latter got together with his most high-profile girlfriend to date, Anna Kournikova, in 2001.
Though Iglesias was better known at the time of their relationship, Vergara made a massive breakthrough in the U.S. several years later, with the 2009 debut of Modern Family.
9. Busy Philipps and Colin Hanks
Colin Hanks and Busy Philipps dated back when they were both students at Loyola Marymount University, as Philipps herself revealed while guest hosting Live with Kelly in 2017.
“He was my college boyfriend!” she explained, shortly before Hanks appeared on the morning show. “We met when I was 18 and Colin was 19… We are very very close friends now.”
Hanks agreed, saying, “We got our first televisions shows within the same week… We were able to go through all the really special moments in a young actor’s lives together.”
10. Ryan Reynolds and Kristen Johnston
Before he was happily married to Blake Lively, Ryan Reynolds had his fair share of relationships with famous women, including ex-fiancee Alanis Morissette and his first wife, Scarlett Johansson. But one of his earlier Hollywood romances was with 3rd Rock from the Sun star, Kristen Johnston.
The Deadpool actor dated the TV celebrity in 1999, while he was starring in the ABC sitcom, Two Guys and a Girl.
11. Fergie and Justin Timberlake
Before famously rocking all-denim couple outfits with Britney Spears, Justin Timberlake had a brief fling with another now-famous pop star, Fergie. The two reportedly dated in 2001, during Timberlake’s boy band days in NSYNC. Meanwhile, Fergie was still part of the girl group Wild Orchid.
“He was 16 and I was 23. It was before he got real heavy with Britney,” said Fergie.
12. Kim Kardashian and Nick Lachey
Following his high-profile divorce from Jessica Simpson, Nick Lachey went on a handful of dates with Kim Kardashian. This was pre-Keeping Up with the Kardashians (remember those days?), so Kardashian was not yet a reality TV star or a tabloid staple.
Lachey later suggested that Kardashian used him to help launch her fame. “Let’s just say this: We went to a movie. No one followed us there. Somehow, mysteriously, when we left, there were 30 photographers waiting outside,” he told Details in 2013.
13. Whitney Houston and Ray J
Before her tragic death in 2012, the diva was linked to Ray J, who is best known for appearing with Kardashian in the now-infamous leaked sex tape. The two, who were 17 years apart in age, had reportedly known each other since Ray J was a young boy and began dating after Whitney Houston’s rocky split from Bobby Brown.
Ray J later appeared on Celebrity Big Brother and confessed that he still harbors feelings of guilt over Houston’s death, saying, “I never really talked to no one about it. I don’t know if I need to more as I’ve accepted it and it’s deep inside of my heart but it still affects me.”
14. Kate Hudson and Nick Jonas
Nick Jonas and Kate Hudson sparked dating rumors in late 2015, when they were photographed together at various public places, including Orlando’s Walt Disney World. The unexpected pair apparently clicked after being introduced by Hudson’s brother and Jonas’ Scream Queens co-star, Oliver Hudson.
Though things never got serious between the pop star and the actress, the two (who are 13 years apart) reportedly had a brief fling before it fizzled out that same year. “Kate’s incredible. We had an unbelievable connection as two humans who just admire things about each other, and see something in each other that’s beautiful,” Jonas later said to Complex magazine, admitting, “… It’s a bizarre matchup to a lot of people.”
Jonas also raved about the actress to Ellen DeGeneres, as seen above.
15. Lenny Kravitz and Nicole Kidman
Nicole Kidman shocked many in February 2017, when she revealed that she was once engaged to Lenny Kravitz. The two were linked back in 2003, but had never publicly confirmed that they were planning on tying the knot.
Kidman had previously admitted to being engaged before meeting her current husband, Keith Urban, and after her divorce from Tom Cruise, but had never named Kravitz as her former fiance.
Kidman made the confession while discussing her Big Little Lies co-star Zoë Kravitz.
“Well, I knew Zoë because I was engaged to her father. It’s all in the family!,” the actress told The Edit, adding that they’re all still close. “I love Lenny. He’s a great guy.”
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