Lindsay Sloane in Seven Girlfriends (1999)

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Chef Tim Daly has never been good at keeping a girlfriend once he's got one, and now he's out to figure out just where he's gone wrong by quizzing Seven Girlfriends (1999). When his former flame dies and the current one—played by d'amazing Olivia D'Abo—says "No way" to his marriage proposal, Tim sets off on a journey to understand why he always ends up a single man. His former fillies are Jamie Gertz, Laura Leighton, Elizabeth Peņa, Mimi Rogers, Katy Selverstone—plus his great old gal pal Melora Hardin, who may or may not be his best chance at love. Your best chance at a Seven Girlfriends chub comes in the fine form of Jennifer Gibson, who bares her right funbag in bed.