Celebrities Who Have Dated Under The Radar: Kim Kardashian, Leann Rimes, Brad Pitt And More! (Photos)

There is no doubt that the celebrity world is one of the smallest ones out there! Before Kim and Kanye or Angelina and Brad, did you know that Kim Kardashian dated Mariah Carey’s husband Nick Cannon? Or that Brad Pitt was linked to fellow celebrity parent Christina Applegate? In fact, Oprah and Roger Ebert even dated back in the day! I’m sure all of the Golden Globes and Oscar after-parties have got to be one of the most awkward places for celebs to bump into their old flames!

Check out our photo gallery of some of the most surprising celebrity hook-ups of celebrity moms and dads from back in the day. I’m sure you’re jaw will drop a few times the same way mine did while putting this together!

  • Lisa Kudrow and Conan O’Brien 1 of 21
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    Phoebe and Conan? No way! Now this one really surprises me! 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," Lisa once said.

    Source via The Huffington Post

  • Tiger Woods and Leann Rimes 2 of 21
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    You'd think these two were made for each other, right? Golf superstar Tiger Woods reportedly dated LeAnn Rimes in 2002. According to an Us Weekly source, the relationship ended when LeAnn's dad thought Tiger, seven years her senior, was too old for her at the time.

    Source The Insider

  • Jenna Dewan and Justin Timberlake 3 of 21
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    Right after his break-up with Britney Spears, Justin Timberlake was linked to actress and professional dancer Jenna Dewan in 2002, before she hit it big playing Nora in 2006's Step Up.

    Source via The Insider

  • Danny Wood and Halle Berry 4 of 21
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    Who couldn't resist New Kids on the Block back in the day? Certainly not Halle Berry! The newly-engaged Oscar-winning actress dated New Kids on the Block singer Danny Wood all the way back in 1989.

    Source The Insider


  • Roger Ebert and Oprah 5 of 21
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    These hook-ups are beginning to blow your mind, aren't they? Roger Ebert and Oprah went on two dates way back when the two were just starting out in Chicago -- and Ebert counted himself as her mentor.

    Source via The Huffington Post

  • Dax Shepard and Kate Hudson 6 of 21
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    Hollywood's golden girl dated the funny man (and new dad!) back in 2007, but their relationship only lasted a couple of months.

    Source via E! Online

  • Amber Rose and Kanye West 7 of 21
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    Before Kim Kardashian, Amber Rose was Kanye West's love of his life. Apparently, Amber's new baby daddy Wiz Khalifa wants to reach out to Kanye so they can have playdates once Kim's baby is born. Awkward much? LOL.

    Source via The Huffington Post

  • David Spade and Julie Bowen 8 of 21
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    David's dating roster reads like a who's who of hot Hollywood blonds: Heather Locklear, Nicollette Sheridan and Playboy Playmate Jillian Grace. In 2002, he added the Modern Familystar to his list, but the couple called it quits after a year of dating.

    Source via E! Online

  • Kristin Davis and Liev Schreiber 9 of 21
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    Liev Schreiber dated Kristin Davis in 2003, and though the two were tight-lipped about their romance, they did pose for pictures together together in 2003. These days, Davis is recently single after splitting with writer Aaron Sorkin, while Schreiber remains in a long-term relationship with Naomi Watts.

    Source via The Insider

  • Ashton Kutcher and January Jones 10 of 21
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    Long before Ashton Kutcher married and divorced Demi Moore and January Jones gave birth to her baby boy (whose father she refuses to reveal), these two gave it a go in the romance department.

    Source via The Huffington Post

  • Robert Downey Jr. and Sarah Jessica Parker 11 of 21
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    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," he said.

    Source via The Huffington Post

  • Seal and Tyra Banks 12 of 21
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    He sure has a thing for supermodels, doesn't he? Seal and Tyra confirmed their budding romance when they stepped out to the Essence Awards in 1996, but broke up shortly thereafter.

    Source via The Huffington Post

  • Jake Gylenhaal and Natalie Portman 13 of 21
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    These two A-listers dated back in 2006 for a brief time, but they still remain close friends. Is it just me, or could Jake and Natalie pass as brother and sister, too?

    Sourve via E! Online

  • Brad Pitt and Christina Applegate 14 of 21
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    Now this one surprised me! Christina Applegate took Brad Pitt to the MTV Movie Awards all the way back in 1989. However the blonde actress ditched him at the awards to go home with another guy. The pair had known each other since Applegate was 16 years old and eventually tried to be more than friends. However Pitt lost out to an unnamed man. Christina later admitted, "I felt really bad about it, I really, really do."

    Source via The Insider

  • Britney Spears and Colin Farrell 15 of 21
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    Britney Spears and Colin Farrell reportedly met on the set of the movie S.W.A.T. when Colin was 26 and Britney was 21. Their romance was brief, but surely full of fireworks, too.

    Source Via The Insider

  • Sandra Bullock and Ryan Gosling 16 of 21
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    Ryan once said of his two former girlfriends, Sandra and Rachel McAdams: "I had two of the greatest girlfriends of all time. I haven't met anybody who could top them." Awww! I wonder what Eva Mendes thinks about that?

    Source via The Huffington Post

  • Nick Lachey and Kim Kardashian 17 of 21
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    Back when Kim Kardashian wasn't a household name, she briefly dated Nick Lachey after his highly publicized divorce from Jessica Simpson in 2006.

    Source via The Insider

  • Enrique Iglesias and Sofia Vergara 18 of 21
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    Talk about a hot hook-up! Who knew singer Enrique Iglesias once dated sexy Modern Family star Sofia Vergara?! According to People, long before getting engaged to businessman Nick Loeb, Vergara was attached to Iglesias in the '90s.

    Source via The Insider

  • Shia LeBeouf and Hilary Duff 19 of 21
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    Shia and Hilary 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.

    Source via The Huffington Post

  • Claire Danes and Matt Damon 20 of 21
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    I could see this one happening. The golden-haired pair of Matt Damon and Claire Danes dated in 1997 while filming The Rainmaker. Now they are both happily married, Matt settling down with former Miami bartender Luciana Barroso, Claire with fellow actor Hugh Dancy.

    Source via The Insider

  • Nick Cannon and Kim Kardashian 21 of 21
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    Long before he was father to "dem babies" with wife Mariah Carey, America's Got Talent host Nick Cannon dated Kim Kardashian.

    Source via The Insider

Photos via

Article Posted 3 years Ago
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