Julie Bowen and David Spade
He: Former Saturday Night Live cast member known for his roles in Tommy Boy, Just Shoot Me, and Joe Dirt, among others.
Status: Julie and David dated from 2002 to 2003, which is maybe less weird than it sounds — in the '90s, they perhaps ran in similar circles, since Julie played Adam Sandler's love interest in 1996's Happy Gilmore. Despite David getting Stevie Nicks to sing "Landslide" on Julie's voicemail, the two broke it off in 2003.
Julie got hitched to current husband Scott Phillips the next year, in 2004, and has three children. David's daughter with Playboy Playmate Jillian Grace was born in 2008, but as far as we know, he is currently single.