Approaching age sixty, Daphne Wilder divorced when she was young, has not dated since, and has raised on her own and has fostered a close, loving relationship with her three daughters, Maggie, Mae and Milly, she now assisting Milly in her successful catering business. Daphne was mother of the bride for a first time at Maggie's wedding, and a second time at Mae's wedding, but she fears there won't be a third and final time for a Milly wedding in insecure Milly attracting only who seem to be the wrong men. Not wanting Milly to turn into another "alone" version of herself at age sixty, Daphne, without telling any of her daughters let alone Milly, decides to take matters into her own hands by placing a personal ad for a potential mate for Milly. Scheduling all seventeen interviews in succession at a restaurant, Daphne finds the ad has attracted one "loser" after another, until she reaches number seventeen, Jason, an architect who is handsome and seems smart, well-bred, successful and forward thinking about his life. The two arrange for Jason to meet Milly by "accident". What Daphne does not anticipate is that there ends up being a number eighteen, Johnny, who witnessed the interviews from the sidelines as the guitarist performing at the restaurant, and while Johnny did approach Daphne in his interest in meeting Milly from what he heard of the interviews, she immediately dismissed him solely because he is a musician and thus irresponsible by nature, much like her ex-husband. In their accidental meetings, Milly embarks on a relationship with both Jason and Johnny concurrently, and upon learning about Johnny in the picture, Daphne starts pushing Jason as the favored one to Milly. Beyond Milly, Jason and Johnny's own thoughts about their two relationships, the two men who know nothing about the other being in Milly's life, a question becomes how Milly eventually learning about the ad, an inevitability, will factor into what happens, not only about Milly's love life but her relationship with her mother. In helping Milly with her love life and only fostered by watching old Gary Cooper movies, Daphne may dredge up latent feelings of romance of her own, it which she may find in the most unlikely of places.

Director: Michael Lehmann

Writer: Karen Leigh Hopkins, Jessie Nelson

Actors: Diane Keaton, Mandy Moore, Gabriel Macht

Production: N/A