Sarah Nolan, a 40-year-old divorced preschool teacher, is urged by her family to date. Showing her photos of potential men, she is not interested in pursuing a relationship. Jake Anderson, another recent divorcé, is in a similar position; his friend Charlie wants to match him with Sherry. However, he prefers focusing on his handcrafted boats.
Sarah's sister Carol visits and they discuss Bob Connor, a parent from school. Sarah finds him attractive but does not want anything complicated. Carol sets up an ad for her on perfectmatch.com, using her high school graduation photo. She is described as voluptuous and her dates "must love dogs" (Sarah is currently caring for her brother Michael's Newfoundland, while he goes through marital problems). She has several disastrous dates with men: a cryer, a criminal, and one who is attracted to teenaged girls.
Jake is confronted by Sherry at an art gallery, who wants to know why he did not call, but he is not interested. Charlie then hands him a copy of Sarah's dating profile, telling him he has a date with her the next day at a dog park. It proves to be awkward: Jake shows up with a borrowed terrier and offends her when he begins to analyze her profile, then he reveals the dog is not really his. When she accuses him of being deceptive, he points out the requirement was "Must love dogs," not "Must own a dog." Sarah leaves abruptly but agrees to see him again.
Sarah and Jake go to dinner, where he asks her why she got divorced. She explains that her ex stopped loving her and was never ready to have children. Now, her ex is with a woman fifteen years younger with a baby on the way. The date progresses back to her house, where they find neither has a condom. They frantically drive around the city seeking condoms, but when they finally find them neither is in the mood.
Jake tells Charlie that Sarah intrigues him so, that night, he tries to call her. Meanwhile, as she has connected with Bob Connor, she shows up at his home but finds him with her much younger co-worker, June. Sensing they are on a date, she flees, dropping her wallet.
Arriving home, Sarah finds her brother Michael drunk over his marital problems, and Jake, who has been taking care of him. Jake and she share a kiss, he then takes Michael home while she lights candles to set the mood. Bob shows up ahead of Jake, returning her wallet. He says he and June are not involved, and then kisses her just as Jake gets back. Upset, he leaves.
Around Thanksgiving Sarah calls Bob, they go to a hotel and have sex. In the morning, he is rude and she realizes he had slept with June. He had not told her because he still wanted to hook up with her.
Meanwhile, Jake takes Sherry to see Doctor Zhivago. Sarah sees him leaving the theater afterward, runs up and begins discussing the film with him. She then notices Sherry and realizes they are on a date. Sarah flees again, and when Sherry asks Jake up to her apartment, he declines, walking home.
Jake runs into a man named Bill outside a coffee shop, not realizing he is Sarah's father. When Jake confesses that he is heartbroken, Bill mentions that he has a daughter who is single but Jake declines.
Having coffee with Sarah later, Bill quotes Jake and she realizes Jake had been talking about her. She heads over to Jake's with the dog, but he is on the lake with his boat, so cannot hear her yelling from the shore. She convinces a girls crew team to take her out to him, eventually diving in and swimming to his boat. Climbing in, Sarah tells Jake how she feels about him and they kiss.
Later, when telling the story of how they met, they say in unison that they found each other at a dog park.
Diane 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. When Cusack tried to make her improv she thought, "I don’t feel that confidence. I start blushing profusely and I get all sweaty and, I don’t know. Old school."
John 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