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    Can You Believe They Dated?

    Not all matches were made in heaven.

  • scott_and_liza
    Scott Baio and Liza Minnelli The "Charles in Charge" star has been very vocal about all the lovely ladies that he's bedded over the years. Some of those ladies include Pamela Anderson and Denise Richards, but the most shocking is Liza Minnelli (shown here). The fling happened when he was 35 and she was 49. And he apparently called it off by saying he didn't want "a long term thing." He also called her body at the time "insane." What a gentleman. Check out which other random pairs have hooked up in Hollywood. (Reuters)
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  • leo_and_claire
    Leonardo DiCaprio and Claire Danes In 1996 these two fresh-faced stars played opposite each other in "Romeo + Juliet." Rumors began immediately that their love affair played out off screen as well.  Claire recently said, "I saw Leo the other day and in some ways our dynamic is absolutely the same, but then it’s like, 'Oh, but wait, we’re big, fat grown-ups!'" And you have a baby on the way with hubby Hugh Dancy, Claire. The dynamic must be a bit different! (Reuters)
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  • Cher and Tom Cruise
    Cher & Tom Cruise. Back in the mid 80's, when Katie Holmes was still a little kid, Tom Cruise dated Cher. The iconic singer told ET: "When we were together he was such a private person. I loved him though, he was amazing."
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  • Sarah Jessica Parker and John F. Kennedy Jr.
    Sarah Jessica Parker & John F. Kennedy Jr.: Maxim's 'unsexiest woman' SJP dated the world's most desired man, the late JFK Jr., for several months in the 90's.
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  • Cameron Diaz and Jared Leto
    Cameron Diaz & Jared Leto: Bright and sunny Cameron Diaz was once engaged to dark and moody Jared Leto.
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  • Whoopi Goldberg and Ted Danson
    Whoopi Goldberg & Ted Danson: Ted stirred up controversy when he began dating his "Made in America" co-star Whoppi Goldberg while still married to his second wife Casey Coates. The duo definitely gave new meaning to the term 'odd couple.'
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  • Fergie and Justin Timberlake
    Fergie & Justin Timberlake: Who knew Fergie was once a cougar?! She dated Justin Timberlake when she was 23 and he was only 16, telling Australia's Courier Mail: "It was before he got real heavy with Britney"
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  • Joaquin Phoenix and Liv Tyler
    Joaquin Phoenix & Liv Tyler: Beauty Liv Tyler dated weirdo Joaquin Phoenix from 1995-1998.
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  • Paris Hilton and Nick Carter
    Paris Hilton & Nick Carter: Paris doesn't exactly have the most discerning taste when it comes to men, but her decision to date Backstreet Boy Nick Carter was pretty random, even for her.
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  • Hilary Duff and Joel Madden
    Hilary Duff & Joel Madden: Before he started making babies with Nicole Richie, Joel Madden was smitten with pure as can be Hilary Duff, who might best be described as his polar opposite.
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  • Brad Pitt and Juliette Lewis
    Brad Pitt & Juliette Lewis: This unlikely duo met on the set of the TV movie "Too Young to Die" in 1990 and began a hot and heavy relationship despite their 10 year age gap (she was 16 and he was 26!). They even lived together for a time and then broke up shortly after.
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  • Renee Zellwger and Jack White
    Renee Zellwger & Jack White: Everyone was scratching their head when clean-cut Renee Zellweger started dating dirty, weird-looking White Stripes frontman Jack White. Didn't last. What a surprise.
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  • Published
    12 Images

    Can You Believe They Dated?

    Not all matches were made in heaven.

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  • Can You Believe They Dated?
  • scott_and_liza
  • leo_and_claire
  • Cher and Tom Cruise
  • Sarah Jessica Parker and John F. Kennedy Jr.
  • Cameron Diaz and Jared Leto
  • Whoopi Goldberg and Ted Danson
  • Fergie and Justin Timberlake
  • Joaquin Phoenix and Liv Tyler
  • Paris Hilton and Nick Carter
  • Hilary Duff and Joel Madden
  • Brad Pitt and Juliette Lewis
  • Renee Zellwger and Jack White