In New York City, independent bookstore, New Day Books, on the Upper Westside has a party to celebrate raising funds to remain in business. Employee Isabelle “Izzy” Grossman mingles with guests while tidying up the shop. Her boss, Lionel, tells her to enjoy herself and take the evening off. As Izzy leaves, Anton Maes, a local author with whom she has been infatuated, gives her copy of his book with a handwritten poetic inscription: “Izzy dear, it’s women like you, make the world liquid and even, still in beauty born.” Arriving at her apartment, Izzy sees her friend Nick waiting by the front door. When he asks to stay the night, Izzy says yes. In the morning, Izzy takes the subway to Delancey Station on the Lower East Side to visit her grandmother, “Bubbie” Ida Kantor. While sitting on a park bench, Bubbie informs Izzy that she has hired Jewish marriage broker Hannah Mandelbaum to find Izzy a husband. After meeting with Hannah, Izzy tells Bubbie that she loves her life with her rent control apartment, a job at a prestigious bookshop, and her modern friends. However, Bubbie insists there is nothing worse than being alone. Later, Izzy meets her friend, Candyce, at the West Side Y.M.C.A. to workout and tells Candyce about Maes’s note in the book. Candyce asks if Maes is married, and Izzy says he is separated. Candyce tries to dissuade her from getting involved with a married man. Undeterred, Izzy decides to telephone Maes. At New Day Books, Izzy obtains Maes’s unlisted telephone number from Lionel, saying she needs to confirm details relating to Maes’s upcoming reading at the store. When she calls, Maes thinks Izzy is his estranged wife, and tells her to meet him at the Provence restaurant. When Izzy arrives, Maes realizes his mistake and invites her to dine with him. She happily agrees. Later at the market, Bubbie informs Izzy that Hannah Mandelbaum has found her a possible match in Sam Posner, the owner of a local pickle stand. Izzy looks down upon being setup with “a pickle man,” but Bubbie tells her not to be a snob. At Bubbie’s apartment, Sam arrives for lunch with Izzy, Bubbie, and Hannah. While they eat, Hannah tells Izzy how Sam is a modern man who understands traditional Jewish values. When Hannah and Bubbie leave the table, Izzy says the matchmaking was her grandmother’s idea, and is not her style. Sam responds by telling her a story about his friend Harry, who wore the same cap for years. When Harry lost the cap, Sam told him to go to the shop across from the pickle stand and buy a new, but different hat. The daughter of the shopkeeper noticed Harry for the first time, as the old cap is not covering his face. The following day, Harry and shopkeeper’s daughter became engaged. When Bubbie and Hannah return, Sam informs them that he would like to take Izzy on a date. However, Izzy declines. As Sam leaves, he tells Izzy there is no harm in trying a new hat. Later at New Day Books, Izzy offers to treat Maes to lunch after his book reading. However, Myla Bondy, his former assistant, interrupts and reminds Maes that he is supposed treat her to lunch. Instead, Maes invites Myla to join him and Izzy. After lunch, Maes leaves with Myla for her apartment, leaving Izzy confused about his feelings toward her. Later, Izzy and her friends, Marilyn Cohen and Karen, attend a bris ceremony for Bart, the infant son of their friend, Ricki. Afterward, Marilyn tells them about her recent bad luck with dating. When asked about her love life, Izzy lies and says she is dating Maes. Later, Izzy is surprised on her birthday with a telephone call from her parents in Florida. When she visits Bubbie, a package arrives containing a birthday cake and a new hat. Recalling the story about Harry, Izzy knows the gift is from Sam Posner. Wearing her new hat, Izzy walks to Sam’s pickle stand. She thanks him, but states she is still not interested in dating him. The following evening, Izzy decides to introduce Sam to her friend Marilyn. She invites Sam to dinner, and instructs Marilyn to be at the restaurant, making their meeting appear coincidental. They arrive at the restaurant and Izzy apologizes for her behavior when she first met him. Sam agrees that the matchmaking meeting was awkward, and tells Izzy he should have spoken to her when he first saw her three and a half years ago. He continues, telling her Hannah has been showing him photographs of her matchmaking clients for years, but he always said no, until he saw Izzy’s picture. Shocked by his admission, Izzy excuses herself, and walks to Marilyn, saying she needs more time with Sam. Marilyn insists on joining them, and Izzy leads her to the table, saying she happened to run into her friend. However, when Sam recalls seeing Marilyn earlier, Marilyn confesses it was Izzy’s plan to have them meet. Telling him about herself, Marilyn hands Sam her telephone number and leaves. Izzy tries to apologize. Instead, Sam says he liked Marilyn’s style, and will be calling her. Later, Izzy tells Bubbie about introducing Sam and Marilyn. After she returns to her apartment, Izzy finds Nick waiting at her door. She tells him about Sam, and how she is starting to like him. The following morning, Bubbie decides to play matchmaker herself, and asks Sam to come over to help around her apartment. When Izzy arrives for her scheduled visit, Sam gets up to leave. Following him, Izzy tells him she had nothing to do with her grandmother inviting him over, but Sam does not believe her. To make amends, she invites him and Marilyn to a reception at the bookstore Saturday for author Pauline Swift. However, Sam tells her he and Marilyn will be at a baseball game. However, on Saturday, Sam arrives at New Day Books, without Marilyn. Izzy invites him inside, and they sit on the floor near Pauline Swift as Lionel, Mark, Cecilia, and Maes surround her. As Pauline makes a suggestion to Maes about improving his writing, Maes becomes irate and accidentally kicks Sam’s head. Not wanting to make a scene, Sam says he will return later when there is more room. Izzy leaves with him, and invites him to her apartment. Later, Nick arrives to talk to Izzy about a fight he had with his wife. When he sees Sam, Nick asks if he is the pickle vendor Izzy told him about. Sam informs Nick that his stand is near Delancey Street. Nick recognizes the location, telling Sam he remembers buying pickles from Sam’s father. Not wanting to leave Nick alone with Izzy, Sam makes an offer for Nick to stay with him and his brother Mickey for the night, and Nick gratefully agrees. Before the men leave, Sam asks Izzy out on a real date, and she accepts. On the evening of her scheduled date with Sam, Maes approaches Izzy and asks her to read his new manuscript. Izzy tells him she is meeting Sam at Bubbie’s apartment, but Maes convinces her to let him wait. Upon arriving at Maes’s home, Izzy calls Sam at Bubbie’s and tells him she will be late. As they wait for Izzy, Bubbie tells Sam about her courtship with the man who became her husband. Meanwhile, Izzy sits on Maes’s sofa bed to read the two-page manuscript. After telling him it is a good start, Maes kisses her. After they both fall off the sofa, Maes promises to purchase a new one after Izzy starts her new job, as he has arranged with Lionel for Izzy to work for him part-time as his assistant. Realizing that Maes never had any feelings for her, Izzy rejects his offer and leaves. Arriving at her grandmother’s, Izzy sees Bubbie asleep on the couch, but no sign of Sam. As she begins to cry, Sam comes from the balcony. Izzy admits she was not working, and that he is too nice a man for her. Confused, Sam asks what she wants. When Izzy is unable to answer his question, Sam kisses her. As they kiss, they are startled by Bubbie awakening. Upon seeing Sam, Bubbie pretends she has never seen him before. Assuming the alcohol has impaired her memory, Izzy prepares Bubbie’s bed. While Izzy is out of the room, Bubbie laughs and tells Sam she was joking. When Izzy returns, Bubbie again feigns not having met Sam, and asks Izzy if she likes him. Izzy admits she does, and promises Sam will be coming with her the next time she visits.