After seeing two of her three stunning daughters happily marry, Daphne Wilder focuses all her worries on Milly, her youngest, most insecure, and unlucky-in-love offspring. Twentysomething Milly has got her career as a chef figured out, but is clueless when it comes to love, attracting a never-ending slew of married, cheating, and closeted men. Taking matters into her own hands, Daphne places a personal ad for her daughter, interviewing the suitors herself and settling on one particularly promising young man named Jason. Meanwhile, clueless to her mother's plans, Milly starts to fall for Johnny, a cute musician who in spite of treating Milly like gold, is hardly what Daphne has in mind for her daughter's future.

Daphne Wilder (Keaton), a mother whose love knows no boundaries. She is the proud mom of three daughters: psychologist Maggie (Lauren Graham), sexy and irreverent Mae (Piper Perabo) and insecure, adorable Milly (Mandy Moore) - who, when it comes to men, is like psychotic flypaper. In order to prevent Milly from making the same mistakes she did, Daphne decides to set her up with the perfect man. Little does Milly know that her mom placed an ad in the online personals to find him. Comic mayhem unfolds as Daphne continues to do the wrong thing for the right reasons...all in the name of love. In a hilarious battle of strong wills, the mother-daughter dynamic is tested in all its fierce, wacky complexity. The girls help Daphne discover the truths and impossibilities of motherly love, all while trying to answer the questions: where does it begin and where should it end?