While appearing on a Season 3 episode of Will & Grace, Piven played Grace's ex-boyfriend, and as Debra Messing recalled to Andy Cohen on Watch What Happens Live!, her experience with Piven was pretty gross. "You know, I had to kiss a lot of boys on that show. And we were rehearsing, and the very first day of rehearsal, he shoved his tongue all the way down to my heart." Messing says she told Piven to take it easy, but he refused to listen. "I was like, 'You know, this is comedy. We don't really go that deep.' And every time he went for it." Not cool.

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