Businessman Sean Moore is preparing to sell off his coffee company to a multi-national conglomerate. His secretary Kate passes on his messages and reminds him that it's his mother's birthday. Sean tells Kate to send flowers and Kate tells him that he has an interview with reporter Elizabeth Carter. He agrees to meet her in his office and she asks him why he's selling the company. Sean's happy to admit that he's in it for the money. Elizabeth then switches to more personal questions, asking about his father's signed baseball that he sold for $8,000 to start his career. Irritated, Sean starts to get a headache and ends the interview. Afterward he opens his desk drawer for aspirin and finds the baseball. He wonders if Elizabeth planted it but Kate insists that the reporter was never to of her sight.
That night, Kate calls to tell him that no one in the office knows about the baseball. Elizabeth calls to set up a follow-up interview and Sean lets the answering machine take it. He then gets a call from another woman, Alicia, asking to come over. They make love and afterward Alicia emphatically says that she loves him and couldn't live without him. Once she's done, he tells her to leave and pays her. Sean reminds her not to go so heavily on the "I love you." As she dresses, Sean finds his old high school jacket in his closet, the jacket he burned years ago. He thinks Alicia is responsible but she denies having ever seeing it and leaves. He finds a letter in the pocket from his first girlfriend, Bess Wicker. It talks about how she couldn't forgive him and she isn't going to California with him.
When Sean goes back to his office and parks in the sub-basement, Elizabeth comes out of the shadows. She accuses him of being afraid to look at his past, and that now he doesn't care about anyone and no one cares about him. She steps into the light and says she loves him, and he realizes that it's Bess. Kate comes out of the elevator and when Sean turns back to Bess, she's vanished.
Sean calls the magazine and asks them about Bess. The editor tells him that they didn't schedule an interview and that Bess died three days ago in a car accident. He wonders why Bess is showing him things from his past and figures that Bess is somehow trying to give him a second chance. He goes to see his mother, Jessica. She's surprised to see him as he wishes her a happy birthday. When he mentions Bess, she says it's a shame that he let her go. Sean shows his mother the baseball and Jessica says that he stole it, breaking his father's heart. He tries to give it to her but she says it's too late to change things and throws it in the sewer before leaving.
Sean gives his sales meeting but the film is home video of Sean's father Paul making a record of their new home. A teenage Sean and Bess are there, clearly in love. On the film, Sean takes the camera and films his mother and father kissing, and Bess saying she loves him. He walks out of the meeting and drives to the house, now empty and abandoned. Bess appears behind him and says she hoped she'd find him there. Sean says that they had planned to get married and buy the house from his parents, but says it's too late to change things. He wonders what Bess wants to give him now but she says that he has to take what he really needs.
Sean turns toward the front door and Bess disappears. He walks inside and finds himself in the past, as a teenager on the day he stole the baseball. The teenage Sean takes the baseball and starts to leave, but hears Bess calling his name. He puts it back s his parents and Bess arrive. Bess admits she wasn't sure if he'd be there. Sean, given a chance to do things over, leaves with Bess for their date. As Paul asks if he needs any money, Sean says he has everything he needs.