There's definitely been some strange celebrity couplings over the years. I'm sure you can think of many, but I wanted to throw out a few of the most, "I can't believe they dated!" worthy.
Mila Kunis & Macaulay Culkin
Nicolas Sarkozy & Mary Kate Olsen
Courtney Love & Edward Norton
Jennifer Aniston & Adam Duritz
Tom Cruise & Cher
Julia Roberts & Lyle Lovett
Ashley Judd & Michael Bolton
Glenn Close & Woody Harrelson
Dennis Rodman & Madonna
Ryan Reynolds & Kristen Johnson
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