Celebrity Odd Couples: 21 Random Romances

Christian Bale’s new acknowledgment that he once antiquated Drew Barrymore made it clear: when it comes to dating, Hollywood can feel as involved — and incestuous — as “Gossip Girl.” And while today’s romances are splashed all over a tabloids, what about a flings and hook-ups of years past? Here, we demeanour behind during 21 weird luminary romances, from Robert Downey Jr. and Sarah Jessica Parker (RDJSJP?) to Sandra Bullock and Ryan Gosling — and a one lady who got George Clooney to contend “I do.”

SLIDESHOW: 21 “They Dated?” Celebrity Couples

• Ryan Gosling, Sandra Bullock

  The hunky heartthrob and humorous lady were together from 2002 to 2003. “I had dual of a biggest girlfriends of all time. we haven’t met anybody who could tip them,”a href=”http://www.usmagazine.com/celebrity-news/news/ryan-gosling-exes-sandra-bullock-rachel-were-the-best-girlfriends-ever-2011179#ixzz1wZWnD4oD” target=”_hplink” Gosling told emUs Weekly/em /ain 2011 (about Bullock and Rachel McAdams, whom he antiquated afterward). We consternation what stream protection Eva Mendes competence have to contend about that?

• Roger Ebert, Oprah Winfrey

  Roger Ebert and Oprah went on dual dates approach behind when a dual were usually starting out in Chicago — and Ebert depends himself as her mentor. “Yes, it is true, we swayed Oprah to turn a many successful and famous lady in a world,” a href=”http://rogerebert.suntimes.com/apps/pbcs.dll/article?AID=/20051116/COMMENTARY/511160301″ target=”_hplink”Ebert wrote in 2005/a.

• Andre Agassi, Brooke Shields

  Nowadays, it’s tough to suppose that one of a many high-profile couples in a ’90s was tennis star Andre Agassi and singer Brooke Shields. The integrate antiquated for 6 years before marrying in 1999; they divorced usually dual years later.

• Lance Armstrong, Ashley Olsen

  In 2007, afterwards 21-year-old Olsen was spotteda href=”http://www.huffingtonpost.com/2007/10/31/lance-armstrong-and-ashle_n_70525.html” target=”_hplink” creation out with Armstrong/a, 15 years her senior, during Rose Bar in New York. Yeah, we don’t unequivocally get it either.

• George Clooney, Talia Balsam

  George Clooney might be a ultimate bachelor, though he did get married, usually once, to singer Talia Balsam. (Balsam is now married to John Slattery of “Mad Men”). brbr”I was married, so we gave it a shot,”a href=”http://www.cbsnews.com/8301-31749_162-20029324-10391698.html” target=”_hplink” Clooney told Piers Morgan/a in 2011. “I’ve proven how good we was during it, and we just…I’m authorised one.”

• Courteney Cox, Michael Keaton

  The “Friends” star and “Batman” actor antiquated a href=”http://www.people.com/people/archive/article/0,,20102215,00.html” target=”_hplink”from 1989 to 1995/a.
  brbr
  (Getty)

• Conan O’Brien, Lisa Kudrow

  These a href=”http://articles.nydailynews.com/2011-06-29/gossip/29737338_1_phoebe-buffay-improv-groundlings” target=”_hplink”two humorous people dated/a when he was a author for “Saturday Night Live” and she was operative as a comedian in Los Angeles. “He was unequivocally smart, unequivocally humorous and he suspicion we was funny, though found we were improved as friends,” a href=”http://xfinity.comcast.net/slideshow/entertainment-forgottencouples/6/” target=”_hplink”Kudrow pronounced of their brief romance/a.

• Sarah Jessica Parker, Robert Downey Jr.

  By his possess admission, Robert Downey Jr. was reduction than a indication beloved to Sarah Jessica Parker, whom he antiquated from 1984 to 1991. “I favourite to drink, and we had a drug problem, and that didn’t taunt with Sarah Jessica, since it is a farthest thing from what she is,” a href=”http://www.huffingtonpost.com/2008/04/16/robert-downey-jr-on-datin_n_97012.html” target=”_hplink”Downey Jr. pronounced of their relationship/a.

• Drew Barrymore, David Arquette

  These dual Hollywood staples were fast related in 1991 — 8 years before they starred together in 1999′s “Never Been Kissed.”

• Alanis Morissette, Ryan Reynolds

  Before Blake, before Scarlett, there was Alanis: Reynolds antiquated associate Canadian Morissette from 2002 until 2007, when they called off their engagement. Morissette after certified that her manuscript a href=”http://www.accesshollywood.com/alanis-morissette-talks-ryan-reynolds-breakup-covering-my-humps_article_10455?__source=rss%257Clatest_news” target=”_hplink”"Flavors of Entanglement” was about their breakup/a.

• Carson Daly, Tara Reid; Katie Holmes, Chris Kelin

  Cutest — and weirdest — double date ever? Carson Daly/Tara Reid and Katie Holmes/Chris Klein are a summary of a ’90s here.

• Moby, Natalie Portman

  According to Moby, his hurl with Portman caused a lot of nerd wrath. “You don’t date Luke Skywalker’s mom and not have them hatred your guts,” a href=”http://www.nypost.com/p/pagesix/item_YRyKLctrCmIeaFysWHXogP#ixzz1wZUpAuA0″ target=”_hplink”he pronounced about their romance/a.

• Jack Nicholson, Lara Flynn Boyle

  The doubtful integrate had an a href=”http://www.popsugar.com/Look-Whos-Back-Together-Again-12062″ target=”_hplink”on-again, off-again relationship/a from 1999-2006.

• Owen Wilson, Sheryl Crow

  The integrate pennyless adult in 2002, though there were no tough feelings. “I adore Owen. He’s so talented, and a great, good person,” a href=”http://www.usatoday.com/life/music/2002/2002-04-15-crow.htm” target=”_hplink”Crow pronounced about a actor a same year.

• Cameron Diaz, Matt Dillon

  The telegenic “There’s Something About Mary” co-stars antiquated for 3 years before bursting in 1998 — a same year a strike comedy strike a large screen.

• Macaulay Culkin, Mila Kunis

  It seems like ages ago, though a href=”http://www.huffingtonpost.com/2011/01/03/its-over-mila-kunis-and-macauley-culkin-breakup_n_803457.html” target=”_hplink”Kunis separate from rumored fiance Culkin/a usually final year, in Sep 2011. They began dating in 2002.

• Sinitta, Simon Cowell

  The “X Factor” decider and ’80s cocktail star were once a energy integrate in a U.K. Even some-more surprisingly, a href=”http://www.usmagazine.com/celebrity-news/news/brad-pitts-ex-sinitta-dishes-on-his-amazing-body-20112411″ target=”_hplink”Sinitta also antiquated Brad Pitt/a in a late ’80s.

• Madonna, Dennis Rodman

  There are a lot of crazy rumors surrounding this doubtful pair, among them that a href=”http://www.hollywood.com/news/Rodman_Surprised_He_Couldnt_Impregnate_Madonna/3466906″ target=”_hplink”Madonna desperately wanted to be assimilated /aby a former basketball star in a early ’90s.

• Billy Corgan, Tila Tequila

  The intrigue between a Smashing Pumpkins frontman and existence star came out of nowhere, and left usually as fast as it arrived.

• Shia LaBeouf, Hilary Duff

  LaBeouf and Duff, who usually gave birth to her initial child, went on an epically bad date — according to LaBeouf himself. “Probably a misfortune date possibly of us have ever had,” a href=”http://www.hollywoodlife.com/2011/06/28/shia-labeouf-megan-fox-transformers-dark-of-the-moon/” target=”_hplink”the “Transformers” star told emDetails/em/a of their unsuccessful connection.

• Emma Stone, Kieran Culkin

  After assembly on a set of 2009′s “Paper Man,” Stone and Culkin were a href=”http://articles.nydailynews.com/2010-04-07/gossip/27061116_1_emma-stone-kieran-culkin-stars” target=”_hplink”rumored to be dating /a. Stone is now now dating “Spiderman” co-star Andrew Garfield.

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