It’s hard to imagine these celebs sharing dating tastes, but eventually they did.
Hollywood circles are a lot smaller than you think. The dating game is a whole different beast when you’re famous, too.
As a result, not every celebrity connection 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.
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Lisa Bonet and Lenny Kravitz were married from 1985 to 1993. Adriana Lima and Lenny dated from 2001 to 2003, during which time they were briefly engaged.
2.
Katie Holmes and Cher both had intense bonds with Tom Cruise.
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While Tom’s time with Katie Holmes is fairly 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? Apparently not much, except for Derek Jeter.
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Derek dated Mariah from 1997-1998 and she credits him with helping her stay strong after he left Tommy Mottola. A decade later, Rachel and Derek dated briefly before she became known for her affair with Tiger Woods.
4.
Elizabeth Taylor and Britney Spears were both scandalously linked to Colin Farrell.
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Colin Farrell and Britney Spears appeared to be dating for a bit in 2003, but his relationship with Elizabeth Taylor prior to her death in 2011 was reportedly a little more serious. They shared what he described as “romantic” but never physically, mostly on late-night phone calls.
5.
Bella Hadid and Serena Williams have both been linked to Drake.
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Drake doesn’t pigeonhole himself, and his past with these two ladies is a case in point. Drake stalked Bella for part of 2014. He was spotted with Serena at various points in 2011 and 2015.
6.
Carrie Ann Inaba dated John Stamos early in her career. Rebecca Romijn came into contact with John a few years later.
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John and Rebecca were married from 1998 to 2005. He is now married to Caitlin McHugh and she is married to Jerry O’Connell.
7.
Cameron Diaz and Bethenny Frankel both met Alex Rodriguez while he was a baseball player.
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Cameron Diaz and Alex Rodriguez made headlines during their short-lived romance from 2010-2011. His brief relationship with Bethenny Frankel in early 2009, shortly after his divorce from Cynthia Scurtis, was much more discreet.
8th.
Amy Winehouse and Ashanti were both enchanted by Nas.
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Amy and Nas have been reported to have a deep connection, although it’s never been fully qualified as a relationship. The two were introduced in 2003 and found they were born on the same day ten years apart and shared something special. He fell in love with another special singer when he and Ashanti hit it off in 2018.
9.
James DeBarge and Matthew McConaughey caught the eye of Janet Jackson at various points in her life.
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Janet Jackson married James DeBarge when she was a beaming 18-year-old. The marriage was annulled the following year when Janet realized she could not help James with his addiction problems. In the years that followed, she experienced many ups and downs. In 2002, she bonded briefly with Matthew after meeting when they were selected to present a Grammy together.
10
Sarah Jessica Parker and Cindy Crawford were both enchanted by the one and only John F. Kennedy Jr.
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JFK Jr. dated Sarah Jessica Parker for about six months in 1992, a time in her life she once described as “the Kennedy fiasco.” He was her rebound from Robert Downey Jr. It wasn’t until he was George in 1995 that he got a glimpse of models, the most notable of which was Cindy.
11.
Harry Styles and Paris Jackson have both been linked to Cara Delevingne.
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Admittedly, all three young stars belong to a larger circle of friends who meet quite often in their own circle. Harry and Cara hung out through the summer and fall of 2013, while she and Paris publicly pushed the limits of their so-called “flirty friendship” in 2018.
12.
The Game and Rob Kardashian both attempted a relationship with Blac Chyna.
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Blac Chyna was linked to the game in 2014 following her split from Tyga. Rob and Chyna got together in 2016 and welcomed baby girl Dream before the end of the year. Unfortunately, the tumultuous couple never found footing and called it quits in 2017.
13.
Chrishell Stause and Lea Michele share an ex in Matthew Morrison.
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Chrishell Stause dated Matthew Morrison from 2004 to 2007 and even got engaged before calling it off. Later that year, he began dating Lea Michele while they were both on Broadway. It wasn’t until two years later that he would play her teacher in Glee.
14
Laurene Powell Jobs was dating Daniel Humm, Demi Moore’s new boyfriend.
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Daniel and Laurene dated sometime between 2019 and 2021. He and Demi are a new couple, having seen each other in March 2022.
15
Julian Lennon and Brian Austin Green are linked through Tori Spelling.
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The son of Beatles legend John Lennon dated Hollywood heiress Tori Spelling in 1991. It was around the time that she was also fooling around with her co-star and longtime friend Brian Austin Green.
16
Max Ehrich (who is engaged to Demi Lovato) has a history of dating starlets including Jennette McCurdy and Sarah Hyland.
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Max Ehrich was still dating Sarah Hyland when he lived back home in New Jersey. The two actually moved to Los Angeles together to get their careers off the ground. About a year later in 2008 things fizzled out. He reportedly dated Jennette McCurdy briefly in 2010, although he later insisted they were just friends.
17
Prince Albert II and Michael Jackson were both special men in Brooke Shields’ life.
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Brooke Shields enjoyed the puppy love with Michael Jackson in the late ’70s and early ’80s, although she never considered it a relationship. In 1983 she had a brief relationship with Prince Albert II of Monaco.
Which celebrities have you been surprised to see or date with the same people? Dish in the comments!
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