20 Celebrity Hook-Ups That You Had No Idea Even Happened

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Image: Jamie McCarthy/Getty Images for TNT / Larry Busacca/Getty Images for NARAS
Image: Jamie McCarthy/Getty Images for TNT / Image: Larry Busacca/Getty Images for NARAS

15. Drake and Kat Dennings

It’s an odd pairing indeed, but on an episode of Ellen, the singer and renowned lothario said he once went on a date with the 2 Broke Girls star Kat Dennings. It doesn’t appear to have turned into more than one dinner out, but oh to have been a fly on the wall…

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Image: Dimitrios Kambouris/Getty Images / Matthew Eisman/Getty Images
Image: Dimitrios Kambouris/Getty Images / Matthew Eisman/Getty Images

14. Madonna and Vanilla Ice

Remember Vanilla Ice, the “white rapper” of the ’90s? No? Well Madonna likely does. She dated the one-hit wonder for about eight months back in 1991. Their bizarre coupling was actually immortalized in Madonna’s racy Sex book, which came out about the same time.

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