Daphne Wilder (played by Diane Keaton) is a fiercely independent and overbearing mother who is determined to find the perfect man for her youngest daughter, Milly (played by Mandy Moore). Daphne is convinced that she knows what's best for her daughter and is willing to go to great lengths to ensure that Milly ends up with the right guy.
After placing a personal ad on an online dating site, Daphne meets a successful architect named Jason (played by Tom Everett Scott) and sets him up with Milly. However, things start to get complicated when Milly also begins dating a musician named Johnny (played by Gabriel Macht), who Daphne considers to be a bad influence on her daughter.
As Daphne becomes more and more obsessed with finding the right man for Milly, her two other daughters, Mae (played by Lauren Graham) and Maggie (played by Piper Perabo), try to reign in their mother's meddling ways. However, Daphne is not one to be deterred and continues to interfere in her daughter's love life, much to the frustration of everyone involved.
In the end, Milly must ultimately decide who she wants to be with, and Daphne must learn to let go and trust that her daughter will make the right decision. Along the way, the family learns important lessons about love, communication, and the importance of allowing those we care about to make their own choices.