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It's hard to imagine these celebs sharing tastes in partners, but at some point they did.
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.
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.
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.
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.
John and Rebecca were married from 1998 to 2005. Today, he is married to Caitlin McHugh, and she is married to Jerry O'Connell.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.