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.