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Jack and Jill vs. the World
2008
 
Freddie Prinze Jr. stars as Jack, an advertising executive who's leading the carefree, glamorous life of a successful young bachelor in Manhattan -- until he meets Jill (Taryn Manning), a newcomer to the city with a distinct devil-may-care streak. The two fall hard for each other and create a mission statement for their relationship, including the cardinal rule, "Be honest" -- a rule that brings unexpected consequences when Jill breaks it.
Synopsis compliments of Netflix
Comedy, Romance
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This was played on lifetime network. Need I say more?
 
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