A rom-com that pairs Michelle Monaghan and Patrick Dempsey as two best friends who have polarizing viewpoints on love and marriage. Tom (Dempsey) is a serial dater and Playboy whose not expecting to get hitched anytime soon. Hannah (Monaghan), on the other hand, longs to get married though she hasn't found Mr. Right yet. Just as Tom starts to change his mind about relationships, Hannah gets engaged. When she asks her best friend to be her "maid" of honor, he reluctantly agrees just so he can attempt to stop the wedding.