CelebrityVideoCelebrity Couplesbrooke shields andre agassi

Celebrity Odd Couples: 21 Random Romances

They Dated? 21 Odd Celebrity Romances
|
Open Image Modal

Christian Bale's recent admission that he once dated Drew Barrymore made it clear: when it comes to dating, Hollywood can feel as convoluted -- and incestuous -- as "Gossip Girl." And while today's romances are splashed all over the tabloids, what about the flings and hook-ups of years past? Here, we look back at 21 bizarre celebrity romances, from Robert Downey Jr. and Sarah Jessica Parker (RDJSJP?) to Sandra Bullock and Ryan Gosling -- plus the one woman who got George Clooney to say "I do."

SLIDESHOW: 21 "They Dated?" Celebrity Couples

Yes, They Dated: Surprising Celebrity Hook-Ups
Ryan Gosling, Sandra Bullock(01 of21)
Open Image Modal
The hunky heartthrob and funny girl were together from 2002 to 2003. "I had two of the greatest girlfriends of all time. I haven't met anybody who could top them," Gosling told Us Weekly in 2011 (about Bullock and Rachel McAdams, whom he dated afterward). We wonder what current amour Eva Mendes might have to say about that? (credit:Getty)
Roger Ebert, Oprah Winfrey(02 of21)
Open Image Modal
Roger Ebert and Oprah went on two dates way back when the two were just starting out in Chicago -- and Ebert counts himself as her mentor. "Yes, it is true, I persuaded Oprah to become the most successful and famous woman in the world," Ebert wrote in 2005. (credit:Getty)
Andre Agassi, Brooke Shields(03 of21)
Open Image Modal
Nowadays, it's hard to imagine that one of the most high-profile couples in the '90s was tennis star Andre Agassi and actress Brooke Shields. The couple dated for six years before marrying in 1999; they divorced just two years later. (credit:Getty)
Lance Armstrong, Ashley Olsen(04 of21)
Open Image Modal
In 2007, then 21-year-old Olsen was spotted making out with Armstrong, 15 years her senior, at Rose Bar in New York. Yeah, we don't really get it either. (credit:Getty)
George Clooney, Talia Balsam(05 of21)
Open Image Modal
George Clooney may be the ultimate bachelor, but he did get married, just once, to actress Talia Balsam. (Balsam is now married to John Slattery of "Mad Men").

"I was married, so I gave it a shot," Clooney told Piers Morgan in 2011. "I've proven how good I was at it, and I just...I'm allowed one." (credit:Getty)
Courteney Cox, Michael Keaton(06 of21)
Open Image Modal
The "Friends" star and "Batman" actor dated from 1989 to 1995.

(Getty) (credit:Getty)
Conan O'Brien, Lisa Kudrow(07 of21)
Open Image Modal
These two funny people dated when he was a writer for "Saturday Night Live" and she was working as a comedian in Los Angeles. "He was really smart, really funny and he thought I was funny, but found we were better as friends," Kudrow said of their brief romance. (credit:Getty)
Sarah Jessica Parker, Robert Downey Jr.(08 of21)
Open Image Modal
By his own admission, Robert Downey Jr. was less than a model boyfriend to Sarah Jessica Parker, whom he dated from 1984 to 1991. "I liked to drink, and I had a drug problem, and that didn't jibe with Sarah Jessica, because it is the furthest thing from what she is," Downey Jr. said of their relationship. (credit:Getty)
Drew Barrymore, David Arquette(09 of21)
Open Image Modal
These two Hollywood staples were briefly linked in 1991 -- eight years before they starred together in 1999's "Never Been Kissed." (credit:Getty)
Alanis Morissette, Ryan Reynolds(10 of21)
Open Image Modal
Before Blake, before Scarlett, there was Alanis: Reynolds dated fellow Canadian Morissette from 2002 until 2007, when they called off their engagement. Morissette later admitted that her album "Flavors of Entanglement" was about their breakup. (credit:Getty)
Carson Daly, Tara Reid; Katie Holmes, Chris Kelin(11 of21)
Open Image Modal
Cutest -- and weirdest -- double date ever? Carson Daly/Tara Reid and Katie Holmes/Chris Klein are the epitome of the '90s here. (credit:Getty)
Moby, Natalie Portman(12 of21)
Open Image Modal
According to Moby, his fling with Portman caused a lot of nerd wrath. "You don't date Luke Skywalker's mom and not have them hate your guts," he said about their romance. (credit:Getty)
Jack Nicholson, Lara Flynn Boyle(13 of21)
Open Image Modal
The unlikely couple had an on-again, off-again relationship from 1999-2006. (credit:Getty)
Owen Wilson, Sheryl Crow(14 of21)
Open Image Modal
The couple broke up in 2002, but there were no hard feelings. "I love Owen. He's so talented, and a great, great person," Crow said about the actor the same year. (credit:Getty)
Cameron Diaz, Matt Dillon(15 of21)
Open Image Modal
The telegenic "There's Something About Mary" co-stars dated for three years before splitting in 1998 -- the same year the hit comedy hit the big screen. (credit:Getty)
Macaulay Culkin, Mila Kunis(16 of21)
Open Image Modal
It seems like ages ago, but Kunis split from rumored fiance Culkin only last year, in September 2011. They began dating in 2002. (credit:Getty)
Sinitta, Simon Cowell(17 of21)
Open Image Modal
The "X Factor" judge and '80s pop star were once a power couple in the U.K. Even more surprisingly, Sinitta also dated Brad Pitt in the late '80s. (credit:Getty)
Madonna, Dennis Rodman(18 of21)
Open Image Modal
There are a lot of crazy rumors surrounding this unlikely pair, among them that Madonna desperately wanted to be impregnated by the former basketball star in the early '90s. (credit:Getty)
Billy Corgan, Tila Tequila(19 of21)
Open Image Modal
The romance between the Smashing Pumpkins frontman and reality star came out of nowhere, and left just as quickly as it arrived. (credit:Getty)
Shia LaBeouf, Hilary Duff(20 of21)
Open Image Modal
LaBeouf and Duff, who just gave birth to her first child, went on an epically bad date -- according to LaBeouf himself. "Probably the worst date either of us have ever had," the "Transformers" star told Details of their failed connection. (credit:Getty)
Emma Stone, Kieran Culkin(21 of21)
Open Image Modal
After meeting on the set of 2009's "Paper Man," Stone and Culkin were rumored to be dating . Stone is now currently dating "Spiderman" co-star Andrew Garfield. (credit:Getty)

Support HuffPost

At HuffPost, we believe that everyone needs high-quality journalism, but we understand that not everyone can afford to pay for expensive news subscriptions. That is why we are committed to providing deeply reported, carefully fact-checked news that is freely accessible to everyone.

Whether you come to HuffPost for updates on the 2024 presidential race, hard-hitting investigations into critical issues facing our country today, or trending stories that make you laugh, we appreciate you. The truth is, news costs money to produce, and we are proud that we have never put our stories behind an expensive paywall.

Would you join us to help keep our stories free for all? Your will go a long way.

Support HuffPost

Before You Go

Suggest a correction
|
Submit a tip