<P> Daphne fears that her daughter cannot find a good man on her own, so she secretly places a personal ad for her daughter . She finds a potential candidate, Jason (Tom Everett Scott), and tries to orchestrate a chance meeting of the two . The plan seems flawless until Milly finds her own date, guitarist Johnny (Gabriel Macht), who happens to be a candidate Daphne rejected before . Milly is unaware of her mother's scheming and begins relationships with both Jason and Johnny at the same time, with neither aware of the other . </P> <P> Inevitably, this double - dating takes its toll and Milly becomes estranged from both Jason and Johnny . In Jason's case, it is because she discovers Daphne's scheming . Meanwhile, Daphne stumbles upon her own perfect match after being alone for many years and begins to challenge her search for the perfect match for Milly . Milly also realizes she has a choice to be the daughter her mother wants her to be, or to be the woman she wants herself to be . Choosing the latter, which comes with a row with her mother, leads her to reconcile with Johnny, a relationship Daphne has realized she should have tried to orchestrate in the first place . </P> <Ul> <Li> Diane Keaton as Daphne Wilder </Li> <Li> Mandy Moore as Milly Wilder </Li> <Li> Gabriel Macht as Johnny Dresden </Li> <Li> Tom Everett Scott as Jason Grant </Li> <Li> Stephen Collins as Joe Dresden, Johnny's father . </Li> <Li> Ty Panitz as Lionel Dresden, Johnny's son . </Li> <Li> Lauren Graham as Maggie Wilder - Decker </Li> <Li> Colin Ferguson as Derek Decker, Maggie's husband . </Li> <Li> Piper Perabo as Mae Wilder </Li> <Li> Matt Champagne as Eli, Mae's husband . </Li> <Li> Zachary Gordon as Little Arthur (Uncredited) </Li> </Ul> <Li> Diane Keaton as Daphne Wilder </Li>

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