A self-help seminar inspires a sixty-something woman to romantically pursue her younger co-worker.
Doris Miller is a shy, eccentric 60-something woman, living alone following the death of her mother, whom she has lived with for her whole life. At the funeral, her brother Todd and his wife Cynthia try to persuade her to sell the house, especially the possessions, as she is a hoarder. Her only close friend is the fiery Roz, though she also gets along with Roz's granddaughter Vivian. On her way to work, where she has been doing data entry for decades, she meets new young co-worker John, with whom she is immediately infatuated. Empowered by self-improvement tapes, Doris decides to go after him..
Doris Miller (Sally Field) is a shy, eccentric 60-something woman, living alone following the death of her mother, whom she has lived with for her whole life. At the funeral, her younger brother Todd (Stephen Root) and his wife (Wendi McLendon-Covey) try to persuade her to sell the house, especially the possessions, as she is a hoarder and has a habit of keeping discarded furniture and other items that she finds on the street. Her only close friend is the fiery Roz (Tyne Daly), though she also gets along with Roz's granddaughter. On her way to work, where she has been working as a data entry worker for decades, she meets a younger co-worker, John (Max Greenfield), whom she is immediately infatuated with. Empowered and inspired by cliched self-improvement tapes, Doris decides to go after him.
Doris finds ways to get John's attention, though the attempts are frequently combined with daydream fantasies about a passionate love affair between them. With the help of Roz's granddaughter (Isabella Acres), she creates a fake social media profile in order to find information about him, and discovers that he loves an electropop band that is planning an upcoming concert in the area. Doris buys a CD for the band, which gets John's attention, and attends the concert, where she meets him and they spend time together. The band is intrigued by Doris and invite her backstage, where they spend a fun evening meeting young artists in the area. John tells her that he and his girlfriend recently broke up over text, and asks her about her love life. She reveals that she was engaged in the past, but when her fiance left for a job in Arizona, she had to decline in order to take care of her mother. When they part for the night, John gives her a friendly kiss goodnight, and Doris is in love.
John is distracted for the next week, and Doris discovers that he has a girlfriend, named Brooklyn. Though Brooklyn is friendly and charming, and John likes her, Doris is devastated. She spends the night drinking wine, and in a drunken fit of anguish, she posts a comment on John's social media wall while using her fake profile, posing as a scorned young woman whom he had a torrid love affair with. The next morning, Todd arrives with her therapist, planning on decluttering Doris's house, but when his wife tries to throw out a pencil Doris stole from John, she angrily throws them out of her house. Todd tells her that he's disappointed in her, and she retorts that he was never around when their mother needed help. He says that it was what worked out the best for his success, and she tells him that she could have had those opportunities, too.
At work, Brooklyn arrives and has a fight with John before breaking up with him; Brooklyn tells Doris later that she had seen the comment on his wall and accused him of cheating on her, and she admits that she was cheated on in the past. After work, John tells her about the incident and invites her to his Thanksgiving for friends. She agrees, and when he asks her if she'd ever be interested in dating a younger man, she assumes that he is interested in her.
Roz tells Doris that she's deluded and that she's making a huge mistake by going after John for he will never return her affections, but an infatuated Doris refuses to listen. She dresses up and goes to the Thanksgiving party, where she meets John's uncle, who is clearly interested in her. During the party, she asks to talk to John in his bedroom. While trying to come onto him, she reveals that she's always liked him and that she was the one to put up the comment that drove him and Brooklyn apart. Upset, John rebuffs her, shocked that his friend would break him up with a girlfriend he was so fond of. When a flustered Doris asks him what he meant by asking her if she was interested in younger men, he admits he was trying to set her up with his uncle, who is a decade younger than Doris -- thus, a younger man. A hurt Doris leaves and invites Roz over for comfort.
Doris invites her therapist over to declutter her house, and she succeeds getting it cleaned up. She also quits her job, and apologizes to John before she leaves. When Doris goes to the elevator, John calls her name, races out of his office, and tells her that he really is interested in her and wants to sincerely begin a relationship with her. They kiss, but this is all revealed to be the last one of Doris's fantasies. In reality, alone, she enters the elevator to leave. After hesitating, John calls out her name and runs toward the elevator. Doris smiles as the doors close.
