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Madonna and Tupac

In 2015, Madonna revealed to Howard Stern that she dated the well-known rapper from 1993 to 1995.

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Ryan Gosling and Sandra Bullock

These two got together on the set of "Murder by Numbers" and were a romance from 2002 to 2003.

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Janet Jackson and Matthew McConaughey

They shared a stage together at the 44th Grammy Awards in 2002. There was a lot of talk about a potential affair.

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Yes, the actress Julie Bowen, best known for her role as Claire Dunphy on "Modern Family," dated comedian David Space for a full year in 2002.

Julie Bowen and David Spade

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After meeting him in 1984, the "Sex and the City" actress dated Robert Downey Jr. for the entire eight years.

Sarah Jessica Parker and Robert Downey Jr.

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After meeting during the filming of "The Royal Tenenbaums," the couple engaged in a passionate relationship that lasted for about a year (2001).

Gwyneth Paltrow and Luke Wilson

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Throughout 1999 and 2000, Jim Carrey grew to be one of Renée Zellweger's most significant male figures. In the movie "Me, Myself, and Irene," they were together, and he became obsessed with her.

Renée Zellweger and Jim Carrey

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Agassi had a brief relationship with Barbra Streisand before to dating Brooke Shields. She was 28 years his senior.

Andre Agassi and Barbra Streisand

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The protagonist of "Pretty Woman" and Cindy Crawford dated for nearly six years, but millennials won't recall this.

Richard Gere and Cindy Crawford

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The protagonists did not appear much in front of cameras, or because the relationship was brief.

Kim Kardashian and Kris Humphries