Odd Celebrity Couples: 41 Romances You Never Knew Existed (PHOTOS)

No one is free from those regretful flings we wish we could forget, nonetheless when it comes to these former luminary couples, we did!

We all remember that Owen Wilson and Kate Hudson were on-off Hollywood sweethearts, nonetheless did we know that a “Zoolander” actor and Sheryl Crow were a thing from 1999 to 2001? How about Johnny Depp and Ellen Barkin or Lance Armstrong and Ashley Olsen? All of these rather peculiar couples managed to find any other, channel age barriers and genres of celebrity in a process.

Check out these celebrities who will certainly make we say, “They dated?!”

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• Owen Wilson, Sheryl Crow

  The integrate pennyless adult in 2002, nonetheless there were no tough feelings. “I venerate 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.

• Johnny Depp, Ellen Barkin

  Before his two-year attribute with Kate Moss, a href=”http://voices.yahoo.com/johnny-depps-love-life-past-present-5708768.html”Johnny Depp fast antiquated Ellen Barkin in 1994/a.

• 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.

• 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.

• George Clooney, Talia Balsam

  George Clooney might be a ultimate bachelor, nonetheless 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.”

• Winona Ryder, Jimmy Fallon

  Winona Ryder and Jimmy Fallon were reportedly related in 2002, nonetheless a href=”http://www.wmagazine.com/celebrities/archive/winona_ryder”she denied a attribute in W magazine/a that same year: “I do date once in a while, and I’ve left out with smashing people in a past. Although not with Jimmy Fallon, who everybody thinks is my boyfriend. We’re usually good friends.”

• 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)

• Helen Hunt, Matthew Broderick

  Helen Hunt and Matthew Broderick gave venerate a shot in 1987 and nonetheless happily any after wasn’t in a cards for a pair, a integrate did forge a lifelong friendship. Hunt and Broderick are even gentle adequate with their attribute that a href=”http://articles.nydailynews.com/2008-04-23/gossip/17895768_1_cinema-society-outfit-onstage”they filmed a sex stage together for 2008′s “Then She Found Me.”/a

• 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, nonetheless 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.

• Ashton Kutcher, Jan Jones

  Long before Ashton Kutcher married and divorced Demi Moore and Jan Jones gave to her baby child (whose father she refuses to reveal), a href=”http://www.huffingtonpost.com/2010/10/27/ashton-kutcher-january-jo_n_774749.html”these dual gave it a go in a intrigue department/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.

• Gary Oldman, Uma Thurman

  How did we skip this? a href=”http://www.zimbio.com/dating/3zGpPZJkBxZ/Gary+Oldman+married+Uma+Thurman/Gary+Oldman”Gary Oldman and Uma Thurman were married/a from 1990 – 1992.

• Jennifer Love Hewitt, Joey Lawrence

  Jennifer Love Hewitt and Joey Lawrence were a href=”http://www.ivillage.com/jennifer-love-hewitt-cheating-famous-boyfriends-book/1-a-142303″a compare done in teen idol heaven/a from 1995 – 1996.

• Scott Baio, Pamela Anderson

  Scott Baio and Pamela Anderson a href=”http://www.people.com/people/archive/article/0,,20061439,00.html”called any other swain in a late ’80s and early ’90s/a.

• Emilio Estevez, Demi Moore

  Emilio Estevez and Demi Moore were romantically tangled from 1985 – 1987. After starring in 1985′s “St. Elmo’s Fire,” a href=”http://www.zimbio.com/dating/aVh7uTRFCeI/Emilio+Estevez+engaged+Demi+Moore/Demi+Moore”the span became intent nonetheless never done it to a church/a.

• 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, nonetheless 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.

• 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 Details/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.

• John Stamos, Marlee Matlin

  Johan Stamos and Marlee Matlin a href=”http://www.theinsider.com/gossip/40647_They_Dated_Surprising_Hookups/index.html?page=71″reportedly antiquated in 1989/a — nonetheless regretful or platonic, a span sojourn good friends a href=”https://twitter.com/MarleeMatlin/status/144285645173555201″and during slightest lift on a Twitter relationship/a.

• Whoopi Goldberg, Ted Danson

  You improved trust it: In 1992, a href=”http://www.people.com/people/archive/article/0,,20110576,00.html”Danson was apparently so soft with Goldberg/a during a filming of “Made in America” that it led to a divorce with his afterwards wife-of-16-years, Casey, a subsequent year. “I’d travel in Whoopi’s shade for a rest of my life–I venerate a woman,” Danson pronounced about Goldberg.

• Sean Lennon, Leelee Sobieski

  John Lennon’s son and Sobieski were speckled canoodling during a Rock Roll Hall Of Fame initiation in 2004, when a former teen star was usually 20 years old.

• Jake Gylenhaal, Natalie Portman

  These teen stars were related twice: first, in 2006 (pictured, strolling in New York); and in 2008, shortly before co-starring in “Brothers.” Gyllenhaal and Portman sojourn pals — a a href=”http://www.popeater.com/2011/01/10/jake-gyllenhaal-roasts-natalie-portman/”latter offering a accessible fry of Portman in Jan 2011/a, when he said: “She is elegant, graceful, has extraordinary eyebrows … is talented, unequivocally short, funny, smart, dedicated, impossibly kind.”

• Ryan Reynolds, Kristen Johnson

  Before Blake, before Scarlett, before Alanis, Reynolds antiquated nonetheless another famous face: Kristen Johnston, of “Third Rock from a Sun” celebrity (pictured together here, in 1999).

• Matthew Morrison, Kristen Bell

  Bell and Morrison both attended New York University, a href=”http://www.usmagazine.com/celebrity-body/news/kristen-bell-reveals-she-once-dated-glees-matt-morrison-2010239″where they “dated really briefly.”/a Also, Bell calls a “Glee” star “Matty.” Everybody contend awww.

• Edward Norton, Courtney Love

  This doubtful integrate antiquated for 3 years in a ’90s after co-starring in “The People vs. Larry Flynt” together, and was even rumored to be engaged. a href=”http://www.huffingtonpost.com/2010/02/26/courtney-love-attacks-edw_n_478073.html”Years later, in 2010, Love would blast Norton on Twitter/a over an purported $300,000 she says a actor due her.

• Minka Kelly, Donald Faison

  Before she got together with Yankees star Derek Jeter, Kelly antiquated a “Clueless” actor for a year, from 2004-2005.

• Brad Pitt, Robin Givens

  A pre-fame Brad Pitt antiquated Givens in 1989, in a midst of a nasty dissection with ex-husband Mike Tyson. “As we go to my automobile she drives adult with a large Brad Pitt,” a href=”http://www.dailymail.co.uk/tvshowbiz/article-2125932/Mike-Tyson-admits-seeing-ex-wife-Robin-Givens-Brad-Pitt-turned-wet-noodle.html#ixzz1xo06DpM1″Tyson recalled/a in Apr 2012 on “Conan O’Brien.” “It usually totally impressed me … we had no appetite to fight.”

• Christina Applegate, Brad Pitt

  The Brad strikes again: This time, with a “Married with Children” singer in 1988.

• Al Pacino, Diane Keaton

  Keaton antiquated her “Godfather” co-star Al Pacino in a ’80s; a attribute dissolved after Keaton pushed a matrimony final on Pacino. She told People: “He’s charming, hilarious, a nonstop talker. There was an aspect of him that was like a mislaid orphan, like this kind of crazy simpleton savant. And oh, gorgeous! we was insane for him. we worked tough on that one.”

• Meg Ryan, Russell Crowe

  Hollywood’s swain and a Australian heartthrob enjoyed a jet-setting intrigue from 1999-2001, to most controversy: Ryan was still married to actor Dennis Quaid when a destiny lovebirds met on set of “Proof of Life. “Dennis was not true to me for a really prolonged time, and that was really painful,” a href=”http://www.theage.com.au/lifestyle/celebrity/meg-ryan-admits-to-breaking-russell-crowes-heart-20090403-9qzr.html”Ryan told InStyle/a. “I found out some-more about that after we was divorced … Russell didn’t mangle adult a marriage.”

• Seal, Tyra Banks

  Seal certain has a thing for telegenic supermodels! Seal and Tyra reliable their budding intrigue when they stepped out to a Essence Awards in 1996, nonetheless pennyless adult shortly thereafter.

• Enrique Iglesias, Sofia Vergara

  It’s bizarre to consider of now, nonetheless Vergara was once some-more ordinarily referred to as a href=”http://www.people.com/people/archive/article/0,,20139975,00.html”Iglesias’ ex/a before attack it large with a ABC sitcom “Modern Family.”

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