It's hard to imagine these celebs sharing tastes in partners, but at some point they did.
Hollywood circles are a lot smaller than you'd think. The dating game is also a whole different beast when you're famous.
As a result, not every celeb hookup or relationship makes headlines. There are some pretty interesting connections there that you wouldn't believe.
1. Lisa Bonet and Adriana Lima both had relationships with Lenny Kravitz.
Lisa Bonet and Lenny Kravitz were married from 1985 to 1993. Adriana Lima and Lenny were together from 2001 to 2003, during which time they were briefly engaged.
2. Katie Holmes and Cher both had intense bonds with Tom Cruise.
While Tom's time with Katie Holmes is pretty well documented, not many people know that the actor dated Cher in 1985, after they met at Madonna and Sean Penn's wedding. He was 23 and she was 38.
3. What do Rachel Uchitel and Mariah Carey have in common? Not a whole lot allegedly, except for Derek Jeter.
Derek dated Mariah from 1997 to 1998, and she credits him with helping her stay strong after leaving Tommy Mottola. A decade later, Rachel and Derek dated briefly before she gained notoriety for her affair with Tiger Woods.
4. Elizabeth Taylor and Britney Spears were both scandalously linked to Colin Farrell.
Colin Farrell and Britney Spears appeared to date a bit in 2003, but his relationship with Elizabeth Taylor before her 2011 death was allegedly a little more serious. They shared something he qualified as "romantic" but never physical, primarily over late-night phone calls.
5. Bella Hadid and Serena Williams have both been linked to Drake.
Drake doesn't pigeonhole himself with a type, and his past with these two ladies exemplifies that. Drake pursued Bella throughout part of 2014. He was spotted with Serena at different points in 2011 and again in points of 2015.
6. Carrie Ann Inaba dated John Stamos early in their careers. Rebecca Romijn connected with John a few short years later.
John and Rebecca were married from 1998 to 2005. Today, he is married to Caitlin McHugh, and she is married to Jerry O'Connell.
7. Cameron Diaz and Bethenny Frankel both got to know Alex Rodriguez in his baseball player days.
Cameron Diaz and Alex Rodriguez made a lot of headlines during their short-lived romance from 2010 to 2011. His brief relationship with Bethenny Frankel in early 2009, just after his divorce from Cynthia Scurtis, was much more discreet.
8. Amy Winehouse and Ashanti were both charmed by Nas.
Amy and Nas were reported to have a deep connection, though it never quite qualified as a relationship. The two were introduced in 2003 and realized they were born on the same day a decade apart and shared something special. He found himself falling for another special singer when he and Ashanti hit it off in 2018.
9. James DeBarge and Matthew McConaughey both caught Janet Jackson's eye at different points in her life.
Janet Jackson married James DeBarge as a bright-eyed 18-year-old. The marriage was annulled the following year as Janet realized she couldn't help James in his struggles with addictions. She went through many ups and downs in the years following. In 2002, she briefly linked up with Matthew after meeting when they were picked to present a Grammy together.
10. Sarah Jessica Parker and Cindy Crawford were both enchanted by the one-of-a-kind John F. Kennedy Jr.
JFK Jr. dated Sarah Jessica Parker for about six months in 1992, a time in her life she once dubbed "the Kennedy fiasco." He was her rebound from Robert Downey Jr. It wasn't until his George days in 1995 that he developed a brief taste of models, the most notable of which was Cindy.
11. Harry Styles and Paris Jackson have both been linked to Cara Delevingne.
Admittedly, all three young stars belong to a larger group of friends who date within their own circles quite a bit. Harry and Cara were hanging out in the summer and fall of 2013, while she and Paris pushed the limits of their so-called "flirty friendship" publicly in 2018.
12. The Game and Rob Kardashian both attempted relationships with Blac Chyna.
Blac Chyna was linked to the Game in 2014, after her split from Tyga. Rob and Chyna linked up in 2016 and welcomed their baby girl, Dream, before the year's end. Sadly, the tumultuous couple never found their footing and called it quits in 2017.
13. Chrishell Stause and Lea Michele share a common ex in Matthew Morrison.
Chrishell Stause dated Matthew Morrison from 2004 to 2007 and even got engaged before calling things off. Later that year, he started dating Lea Michele while they were both on the Broadway circuit. It wouldn't be until two years later that he'd play her teacher on Glee.
14. Laurene Powell Jobs dated Demi Moore's new beau, Daniel Humm.
Daniel and Laurene dated from sometime in 2019 through 2021. He and Demi are a new item, having started seeing each other in March 2022.
15. Julian Lennon and Brian Austin Green are connected through Tori Spelling.
The son of Beatles legend John Lennon dated Hollywood heiress Tori Spelling in 1991. It was around the time she was also fooling around with co-star and longtime friend Brian Austin Green.
16. Max Ehrich (of being engaged to Demi Lovato fame) has a history of dating starlets, including Jennette McCurdy and Sarah Hyland.
Max Ehrich was still dating Sarah Hyland when he lived at home in New Jersey. The two actually moved to Los Angeles together to get their careers off the ground. Things fizzled out about a year later in 2008. He briefly allegedly dated Jennette McCurdy in 2010, though he later insisted they were just friends.
17. Prince Albert II and Michael Jackson were both special men in Brooke Shields' life.
Brooke Shields enjoyed puppy love with Michael Jackson in the late '70s and early '80s, though she never considered it a relationship. In 1983, she had a brief relationship with Prince Albert II of Monaco.
What celebrities have you been surprised to see hook up with or date the same people? Dish in the comments!
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