Plot

A meddling mother tries to set her daughter up with the right man so her kid won't follow in her footsteps.

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.—Huggo

Daphne Wilder is a mother whose love knows no bounds or boundaries. She is the proud mom of three daughters: stable psychologist Maggie, sexy and irreverent Mae and insecure, adorable Milly - who, when it comes to men, is like psychotic flypaper. In order to prevent her youngest from making the same mistakes she did, Daphne decides to set Milly up with the perfect man. Little does Milly know, however, that her mom placed an ad in the on-line 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 battle of strong wills, the mother-daughter dynamic is tested in all its fierce, wacky complexity. The girls help Daphne finally discover the truths and impossibilities of motherly love, all while trying to answer the questions: where does it begin and where should it end?—anonymous

Daphne Wilder (Diane Keaton) is a mother of three daughters: stable 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.

Daphne's 2 elder daughters are happily married but Milly has recently broken up with her boyfriend, and Daphne is concerned. Daphne has made several attempts to set up Milly on a date before, but Milly has this loud, nervous laugh which drives everyone away. Milly also has one breast smaller than the other. Milly is a wedding cake specialist and has catered to many weddings without finding love on her own. Milly seems to attract the worst guys. She once went out with a man who just got back together with his wife, and once with a man who didn't think twice before hitting on Milly's best friend.

Maggie tells Daphne that she has to leave Milly alone and quit trying to make her feel so insecure. Mae tells Daphne to stop being a helicopter as she is hovering all over Milly's dating life. Maggie says that Daphne is fixating on Milly to avoid dealing with a very big milestone birthday that Daphne has coming up. Daphne says that in the 20s it is still OK, but 20 years later and Milly could end up all alone, just like Daphne herself. Daphne has a way to get Milly to agree to whatever she wants by saying "Because I Said So".

Daphne fears that her daughter cannot find a good man on her own, so she secretly places a personal ad for her daughter. She meets all potential candidates at the same bar where Johnny is a guitarist. Before meeting Jason, Daphne weeds out a lot of weirdos who are interested in dating Milly. A female therapist approaches Daphne and wants to enroll her in a seminar about letting go. This is when Johnny approaches Daphne and rescues her from the situation. Johnny learns that Daphne is looking for a date for her daughter Milly and Milly has no clue that this is happening behind her back.

This is when Daphne finds a potential candidate, Jason (Tom Everett Scott), and tries to orchestrate a chance meeting of the two. Jason is an architect and comes from a respectable family and claims that he is a workaholic. He speaks Italian and likes wines. Jason is charming and witty and swipes Daphne off her feet. Johnny approaches Daphne again and says that Jason was playing her and says that he had empty eyes. Johnny wants to be the one to meet Milly, but Daphne rejects him since musicians break people's hearts. He says that maybe Daphne doesn't know what is best for Milly.

Daphne gets Milly to wear a Polka dot dress (as Jason admires Daphne's dress) and sends her to cater for Jason's company's 10th anniversary. 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.

Meanwhile, Maggie finds out from one of her therapy patients that he is in depression as he got rejected by a mother looking for a dating worthy guy for her daughter. Maggie figures out that the mother is Daphne by her catchphrase "Because I Said So". Maggie confronts Daphne, but she is adamant that she is doing the right thing and dares Maggie to tell Milly.

Daphne finds out that Milly is dating another guy on the side and is devastated to find that it is Johnny. Johnny is a charming guy who is interested in what Milly wants. Johnny lives with his father Joe (Stephen Collins) and has a son named Lionel.

Jason is essentially a bad guy & doesn't allow Milly any freedom. He decides where they go for dates, or what they eat when they are together and so on. Daphne keeps pushing him even when Milly doesn't like him. Daphne tells Milly that she also once had a choice between a sweet responsible guy like Jason, and Milly's father. She picked Milly's father and regretted it. Daphne sub-consciously nudges Milly to go for Jason. Daphne says that Johnny has heartbreak written all over it and says that as a mother she loves her enough to tell her the complete truth. Milly says that this is just her version of the truth as she believes that Johnny is a great parent. Jason would make Milly feel really bad for every little mistake, but Johnny would make her feel comfortable and supported. Johnny has a way of calming Milly down and he genuinely wants to spend time with her. Jason wants to have 4 kids and has even thought of their names. Johnny wants to know what Milly wants.

At Daphne's big birthday party, Jason invites Milly to meet his parents and Daphne tries to control what Milly should wear. Milly confronts Daphne to stop controlling her and calls her out of control. But then Daphne pretends to have a break-down. The girls have a rick-paper-scissors contest to see who gets to keep Daphne till she recovers. Daphne cheats to ensure she stays with Milly.

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 when she picks up Daphne's phone (while she was sleeping) and the caller was calling about her personal ad. But Milly assumes that Daphne had placed the personal ad for herself.

Meanwhile, Daphne stumbles upon her own perfect match after being alone for many years. Joe meets Daphne when Milly was out on a date with Johnny and he didn't have keys to the house, so he brought Lionel to Milly's. They watch a movie together and end up kissing each other. Milly goes out to dinner with Jason's family and Johnny sees her when Jason drops her back home. Johnny is really hurt and breaks up with Milly. Milly learns from Jason that Daphne's personal ad was for Milly. Milly tells Jason that she never liked what he ordered for her, he ignored her when she wanted to talk, and actually liked her hyena laugh and the Polka dot dress that Daphne made her buy. Milly says that she would have dumped Jason a long time ago, if not for Daphne.

Milly 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 is what she should never have tried to orchestrate in the first place.

Daphne falls in love with the Johnny's dad. Eventually Daphne realizes her mistake and Milly & Johnny get together. Daphne marries his dad.