Tom Thompson [David Schwimmer] still lives with his mother, moving through days that feel routine and unfinished, until Ruth Abernathy [Barbara Hershey] reaches out with news that her son Bill—the man Tom barely recalls—has died by suicide and she asks him to deliver the eulogy. Tom, despite not remembering Bill, agrees to serve as a pallbearer, a decision that unsettles Ruth and unsettles Bill’s relatives while amusing his friends. Meanwhile, his high school crush, Julie DeMarco [Gwyneth Paltrow], reappears in town, stirring old but fragile possibilities and adding a complicated tension to an already heavy day.
At the funeral, Tom’s vague, impersonal eulogy confuses the Abernathys and amuses his friends. Julie, upset by the display, tries to leave as Bill’s casket is carried out of the church, but Tom drags the casket and the pallbearers after her. When asked if she knew Bill, Julie admits she didn’t, but she was saddened to see him in the casket. Her reaction to the scene upsets Bill’s relatives, and Tom is relieved of his pallbearer duties. Ruth, visibly hurt, tells Tom that he is in Bill’s will, a revelation that twists the day’s events even further.
Afterwards, Tom calls Julie and she suggests bringing Scott [Michael Vartan] and Cynthia [Toni Collette] along for a double date. At dinner, Julie and Scott seem to click, while Tom’s conversation with Julie remains awkward. Scott notes that Tom still lives with his mother, which annoys Tom and fuels the hesitation in his budding connection with Julie. He drives her home, and she reveals that she remembers him from high school. As Tom leans in for a kiss, Julie turns away and they collide, scrambling to explain the mixed signals as she explains she’s moving away.
Later, Tom faces rejection at a second job interview and ends up at Ruth’s to help pack Bill’s room. Forlornly paging through old photos of Bill, Tom and Ruth share a kiss and become intimate. Ruth explains Bill’s father died in the war, and Tom reveals that Bill’s supposed love interest was invented from Tom’s own crush on Julie, a confession that deepens their bond. Their relationship continues, built on this strange, intertwined memoryscape.
Tom begins to spy on Julie from his car as she works at a record store. One evening, he sees her closing with Scott entering the shop, and Scott kisses her. Scott notices Tom and drives away in a rush. The next morning, Julie tells Tom about Scott’s kiss, unaware that he witnessed the moment. They reminisce about the high school band and Julie hints at wanting to take a break from life, planning to drive away for a year to be on her own, before inviting Tom to a concert. Tom’s world shifts again when he’s pulled into an Abernathy family gathering at Ruth’s, and he realizes Ruth has overheard him talking about their date. A broken-down car leads Julie to find Ruth’s charm bracelet, and Tom explains that his involvement with Ruth was about helping Bill’s mother after the funeral, a misunderstanding that Ruth interprets as a purely platonic friendship.
After a tow truck ferries Tom and Julie back to his house, Tom slips into his mother’s room to grab her car keys, only for Ruth to enter as well. Tom confesses that he once wanted to dance with Ruth at a school dance, and they share a kiss. Ruth’s call interrupts, and she suggests a new plan; Tom writes and mails a bracelet-wrapped letter to end things with Ruth, choosing to continue dating Julie. On Julie’s birthday, she asks him to meet her parents, while Ruth arrives with the envelope that might end his relationship. At brunch with Julie’s parents, her father disapproves of them, and Tom begs Julie not to leave for a year. Ruth interrupts the moment, humiliating him in front of the family.
At Brad’s [Michael Rapaport] bachelor party, Tom makes a scene, insisting that Brad not marry Lauren [Bitty Schram], calling Lauren an albatross around his neck and suggesting that Scott agrees with him. The following day, Scott apologizes and the two men reconcile. As they recall their childhood, they realize there was another Tom who moved away after junior high, a memory that helps Ruth come to terms with her own grief for her son and Tom’s longing for his childhood crush. Tom brings the other Tom to Ruth, who appreciates the gesture as a way to reminisce and heal. In the end, they understand that both Ruth and Tom needed someone to anchor their memories—the mother mourning her son, and Tom pining for a simpler, earlier affection.
At Brad’s wedding, Tom supports Brad’s marriage to Lauren, while Scott and Cynthia also find reconciliation. Tom hands Julie his car keys for her upcoming trip, and she hints that she still wants to dance. With a new job secured, Tom moves into Julie’s apartment while she’s away, leaving a future that remains open but hopeful, built on honesty, old connections, and the delicate balance between memory and moving forward.
