In 1997, Sarah Huttinger, Jennifer Aniston, a writer for The New York Times who specializes in obituaries and wedding announcements, returns to her hometown of Pasadena, California, for her younger sister Annie’s wedding, accompanied by her fiancé, Jeff Daly. While sharing nerves about commitment with her grandmother, Katharine Richelieu Shirley MacLaine, Sarah reveals that she’s unsure about saying “I do.” Katharine lets slip a secret about her late daughter Jocelyn, Sarah’s mother, who reportedly ran off to Cabo San Lucas a week before her own wedding.
Sarah then visits Jocelyn’s best friend, Aunt Mitsy, who fills in more history: Jocelyn spent time with their prep school classmate Beau Burroughs Mark Ruffalo the week before her wedding to Sarah’s father Earl. Mitsy also notes that Beau was friends with Charles Webb, the author of The Graduate, adding a literary echo to the family story. Jeff reminds Sarah that her parents were married just short of nine months before her birth, which makes her wonder if Beau could be her biological father. The taint of doubt grows as she privately accuses Katharine of being the inspiration for Mrs. Robinson, the guarded seductress in The Graduate who helped texture her mother’s choices.
After the wedding, Sarah travels to San Francisco to confront Beau, who has become a wealthy Silicon Valley Internet visionary. Beau acknowledges sleeping with both Jocelyn and Katharine, but insists he could not be the father because he is sterile after a blunt testicular trauma suffered in a high school soccer accident. They share drinks, and the next morning Sarah awakens in Beau’s Half Moon Bay home—the third generation in her family to sleep with Beau.
Despite lingering guilt, Beau convinces Sarah to be his date at a charity ball, where she meets his son Blake. Beau explains that his wife had wanted a biological child and therefore used artificial insemination with a sperm donor. Mollified, Sarah kisses Beau, but is soon discovered by Jeff, who has traveled to California to find her after she disappeared. An argument erupts, and Jeff leaves for New York City.
Back in Pasadena, Katharine explodes with anger when she learns that Beau has slept with her granddaughter. The two women then learn Annie suffered an anxiety attack while flying to her honeymoon and wants to talk to Sarah. In a candid conversation, Sarah reveals the interwoven history of three generations of Richelieu/Huttinger women with Beau, and she reassures Annie that she is truly in love with her husband Scott, which helps her realize she is ready to marry Jeff.
A crucial layer of the family mystery is revealed: Earl, Sarah’s father, was the one who accidentally caused Beau’s injury years earlier. This news makes Beau wary around Earl, though Katharine takes pleasure in the revelation. Earl admits he always knew about Jocelyn and Beau’s affair; Jocelyn had returned to him because she loved him and wanted a life with him, and on the night she came back, Sarah was conceived. This timing helps to explain the close proximity of the wedding dates and Sarah’s own birth.
With clarity and a renewed sense of commitment, Sarah decides to win Jeff back. She returns to New York and lays her feelings bare, and the couple reconciles on the condition that, if they ever have a daughter, she will not be allowed anywhere near Beau. The story concludes with the wedding of Sarah and Jeff, closing a circle of family intrigue with a promise of possibility for the future.
