New York City. Rafi Gardet (Uma Thurman) comes to see her therapist, Lisa Metzger (Meryl Streep), and tells her she has signed her divorce papers. She is distressed because she has suddenly started to think she wants to have children. Lisa tells her she should try to live in the now, for now. Dave Bloomberg (Bryan Greenberg) is at home when his friend Morris calls. Dave joins Morris (Jon Abrahams) as he goes to see a girl he who has dumped him after their first date. Morris smears a cream pie in her face, which seems to be his usual approach to this situation.
This time, though, the girl calls her brothers out from the house, and Dave and Morris do a quick escape in their car. Dave goes to see a movie with a girl. In front of the theatre he meets an acquiantance, Randall (Zak Orth), who introduces him to his friends Katherine (Annie Parisse) and Rafi. When Dave goes to the bathroom he finds himself locked out of the theatre, along with Rafi; they exhange looks.
After the movie they all go out, and Dave and his date argue over whether or not they are dating. Later, Dave is in his bedroom with the phone. He calls Rafi, but hangs up. He calls again and finds the nerve to ask her out. There's noise in the background; he tells her it's his roommates, but it's actually his grandparents (Jerry Adler and Doris Belack), who he lives with.
Dave picks Rafi up at her apartment building; he finds the doorman (Ato Essandoh) somewhat uncommunicative. At the restaurant he talks about the quirks of his Jewish family. They buy beer at an all-night store, and Dave has to show ID. Rafi asks Dave how old he is; he circles the subject, but they establish that she is 37 and he is 23. That's a bigger age difference than Rafi thought, but Dave convinces her to continue the date, and he takes her to a secret garden hidden behind a gate. Rafi is back with her therapist. We flash back to the garden, where Rafi and Dave chat and kiss. Rafi tells Lisa about the age difference - though she lies and says Dave is 27 - and she isn't sure she should be getting into a relationship, but Lisa says it's a good thing.
Later Dave talks to his mother on the phone; she is worried that he is dating a girl who isn't Jewish. Rafi talks to her friend Katherine about Dave. Dave goes to his family home, and we discover that his mother is Rafi's therapist. After dinner they have argue; Lisa believes faith to be central in a person's life and thinks it causes too many problems to marry outside your faith. Dave says she sounds like an after-school special.
He also tells her that the woman he is dating is older than him; he says 27. Dave visits Rafi at her apartment; he unsuccessfully tries to make the doorman laugh. They talk about art, listen to jazz and kiss. Dave and Morris go to a bakery to get Morris another cream pie, and Dave tells Morris about his feelings for Rafi. Dave's parents talk about how they can get Dave to date Jewish girls. Dave and Rafi go out again and end up sleeping together.
Rafi goes to see Lisa again and talks excitedly about Dave. She blurts out his real age and admits that she was and is embarrassed by the age difference. She also says he is an artist, though he is not very confident about it and his family is unsupportive; we see a flashback of her and Dave talking about this. Lisa looks startled and asks where he lives.
She realizes that they are talking about her son and breaks off their session. Soon she's on the couch of another therapist (Madhur Jaffrey), asking for advice on what to do. She decides to stay on as Rafi's therapist, not revealing anything. Dave takes Rafi out again, and they have a candlelight dinner next to a big painting by Rafi's favourite artist. Another day she comes to see him play basketball and takes him home to bed. Back at Lisa's office, Rafi talks about how much sex she and Dave have, how happy she is and how beautiful his penis is. They also touch on personal hygiene, and Rafi explains how Dave never used Q-tips before he met her, complete with a flashback. But Rafi also talks about her doubts about whether she and Dave can have a serious relationship.
In another scene, Dave tells Rafi how his mother and family do not accept that Dave is dating a non-Jew. He remembers how he introduced a former girlfriend, who was black, to his grandmother, and how she reacted by wacking herself on the head with a frying pan. On the same day, Dave loses his job and has to find a new place to stay because his grandparents are swapping apartments with relatives. He goes to see Rafi at work, at a fashion shoot, and offends her employer. But he is soon forgiven, and at night they go dancing. Rafi insists they go to Dave's place after; she finds out he lives with his grandparents and laughs. She sees his paintings for the first time and tells him he should paint for a living. Dave drops off some stuff at his parents' place, saying he is staying with Morris for a while.
When Rafi arrives for her appointment with Lisa at the office next door, Lisa narrowly keeps the two from meeting. Rafi tells her that Dave is moving in with her. That weekend the couple go to the Hamptons to visit Rafi's friends, a gay couple (David Costabile and Will McCormack), along with Randall, also gay, and Katherine. The group discuss politics and arts, but Dave feels excluded and feels like he's being tested. Randall expresses concern that Dave at his age might not be able to give her what she needs, especially when it comes to children. Dave and Rafi go to a gallery opening.
She lets her contacts know about his art, but she doesn't introduce him to some of her friends. Dave still doesn't have a job and just hangs around Rafi's apartment all day. One day Lisa goes into a furniture store with her husband, and they have to hide when she sees Dave and Rafi there. In their next consultation, Rafi tells Lisa about her problems with Dave, but Lisa interrupts her. She tells Rafi the truth. Rafi is shocked and angry. She tells Dave, and Dave argues with his mother on the phone.
Dave brings Morris to Rafi's apartment one day, but hides him in a closet when Rafi comes home early because she doesn't like other people in the apartment. She finds out and blames Dave for acting like a child. They fight. Later at a restaurant Rafi breaks up with Dave. One of Rafi's art connections comes to see Dave's pictures. He buys two and wants to set up a show.
Dave also gets his own apartment. He is still down about Rafi, but Morris takes him out, and Dave ends up bringing a girl home with him - a model he previously met at Rafi's photo shoot (Mini Anden). But soon after he and Rafi meet in a grocery store and rush back to his place to have sex. They rekindle their relationship, and Dave talks his mother into having them over for dinner with the whole family. Rafi and Lisa make friends again, and the family seem to relax about the idea of Rafi and Dave together, and of Dave being a painter. Rafi mentions the possibility of having children with Dave. Rafi learns of Dave's night with the model.
Heartbroken, she confronts him. Dave talks to his mother, who tells him she understands his love for Rafi, but that sometimes good things come to an end. One night Dave goes to see Rafi, who comes home at the same moment. The doorman makes sure they meet in the elevator. Dave apologizes. Next we see them in bed together. Dave says he wants to make a baby with her. Rafi says she can't let that happen.
One year later, winter. Dave and Morris are walking down a street. Dave is talking about leaving and seeing the world. He realizes he forgot his hat in a restaurant, and he goes back for it. At the restaurant he sees Rafi and her friends at a table. He turns away and goes outside, but then he wipes a circle in the frost-clad window.
Rafi sees him, they look at each other, she smiles. We see flashbacks of their relationship. Then Dave raises his hand as goodbye and walks away in the snow..