Plot[ edit ] Sarah Nolan, an attractive year-old divorced preschool teacher, is urged by her family to date more. Although they show her photos of men with whom they want to set her up, Sarah does not seem interested in pursuing any relationships. Jake Anderson, another recent divorcee, finds himself in a similar position; his lawyer, Charlie, wants to set him up with a woman named Sherry.
However, Jake would rather focus on creating his handcrafted boats. Sarah's sister Carol visits and they discuss Bob Connor, a parent from school. Sarah is attracted to him but does not want anything complicated. Carol reveals she set up an ad for Sarah on an online dating site, perfectmatch. The description declares she is voluptuous and that her dates "must love dogs" Sarah is currently caring for her brother Michael's Newfoundland dog, " Mother Teresa ", while he goes through his own marital problems.
Sarah proceeds to suffer through several disastrous dates with men who cannot stop crying, are criminal, or like girls who are barely legal. Jake is confronted by Sherry at an art gallery; she is curious why he did not call her, but again Jake does not seem interested. Charlie then hands him a printout of Sarah's dating profile and tells Jake he has a date with her the next day at a dog park. The date proves to be awkward: Jake shows up with a borrowed terrier and offends Sarah when he begins to analyze her profile.
Even worse, he reveals that the dog is not really his. When she accuses him of being deceptive he points out that the requirement was "Must love dogs," not "Must own a dog.
Sarah and Jake go on a dinner date where he asks her why she is not with her husband anymore. She explains that he just stopped loving her and that he was never ready to have children. Sarah acknowledges that her ex-husband is now with a woman fifteen years younger than she with a baby on the way. The date progresses back to Sarah's house where they discover that neither has a condom. They hastily drive around but when they finally find protection neither of them is in the mood.
Jake and Charlie are discussing Sarah when he admits that she intrigued him. That night, Jake tries to call Sarah. Meanwhile, Sarah has connected with Bob Connor. She checks to see if Bob is home but discovers he is with June, one of her co-workers.
Sarah assumes they are on a date, and while fleeing the scene she drops her wallet. Sarah arrives home to find her brother Michael, who is drunkenly dealing with his own marital problems, and Jake, who has been taking care of him. Jake takes Sarah rowing and they share a kiss. Afterward he takes Michael home while Sarah lights candles and sets the mood. But Bob shows up instead of Jake. He returns her wallet, explains that he and June are not involved, and then kisses Sarah just as Jake gets back.
Around Thanksgiving Sarah calls Bob and they go to a hotel and have sex. In the morning Bob is rude to Sarah and during the drive home Sarah realizes that he really did sleep with June. He admits he didn't tell her because he thought they were good together and didn't want that getting in the way. Meanwhile, Jake is talked into taking Sherry to see Doctor Zhivago. Sarah notices Jake leaving the theater afterward, but while discussing the film with him she notices Sherry and realizes the two of them are on a date.
Sarah flees again, and when Sherry asks Jake up to her apartment, he declines and instead walks home. Jake runs into a man named Bill outside a coffee shop, not realizing that this man is Sarah's father. When Jake confesses that he is heartbroken, Bill mentions that he has a daughter who is single but Jake declines. While drinking coffee with Sarah later, Bill quotes something that Jake said to him and Sarah realizes that Jake was talking about her.
She heads over to Jake's with Mother Teresa, but he is out on the lake with his boat. When Jake can't hear her yelling from the shore she convinces a girls crew team to take her out to him. Eventually she dives in and swims over to his boat. After climbing in Sarah tells Jake how she feels about him and they kiss.
Later, when telling the story of how they met, they mention in unison that they found each other at a dog park. Cast[ edit ] Diane Lane as Sarah Nolan: Lane took the part because she wanted to do something different from her recent roles and wanted to keep the shoot local. She was extremely nervous about any improv that Cusack added to the film. Cusack was about to do another film in Europe but it fell through at the last minute. He met with Goldberg and after reading the script they asked him to be in the film.
Impressed with the actors that were already signed on, Cusack thought, "that's a pretty great pedigree, so I was kind of happy to be asked to join such a great group. Kyra Sedgwick was originally cast in the part.