Who: Emmy-winning Jimmy Kimmel Live! host and comedian Jimmy Kimmel, 54, and Emmy-winning comedian Sarah Silverman, 51.

How They Met: The comedians first met in an aptly comedic way, at the N.Y. Friars Club Roast of Hugh Hefner in 2001. Kimmel was hosting and Silverman was obligated to make a joke at his expense. Her blow of choice? Describing her future boyfriend as "fat" with "no charisma."