At a New Year’s Eve party in the final minutes of 1999, the angels meet Angela, their new assignment. Tess tells Monica that Angela is reluctant to enter the new millennium because she does not want to give up the past. Tess also informs her that Angela has forgotten about an important appointment that she made many years ago. In the crowded chaos of the party, Andrew, working as a waiter, accidentally spills some champagne on Angela’s dress. Angela graciously retreats to the ladies’ room where she meets Monica, the attendant, who is able to clean her dress. Monica recites a poem to Angela, “Oh! To be alive in such an age!” and this triggers a childhood memory about Angela’s father.

When she leaves the ladies’ room, the commitment-weary Angela becomes nervous when she oversees her escort, Nick, showing Andrew an engagement ring. Later, on the terrace, Angela tells Andrew about her father, Carl, whom she idolized. He was full of spirit and had a love of great poetry. Angela remembers that she and her father buried a time capsule in 1955 and made a pact to return on January 1, 2000 to dig it up. Andrew encourages her to keep the appointment. Somewhat reluctant at first to unearth old memories, Angela agrees to make the overnight trip to her childhood home with Monica and Andrew.

The next morning they arrive at the house which is now a bed and breakfast run by Tess. They check in and Angela explores her memories, but is reluctant to dig up the time capsule. Instead, she wants to wait for her father. Angela tells the angels more about Carl — how he abandoned her without explanation when she was a child. She presumes he is dead by now. Angela is angry when she realizes that this traumatic event is the source of her own inability to make a marriage commitment. Finally, Angela digs up the time capsule. She is surprised to find the capsule filled with twenty years’ worth of letters from her father. Angela and the angels begin to read the emotional letters — the final letter accompanied with a note from a doctor diagnosing Carl as a manic-depressive. This enables Angela to remember an incident in which Carl brought her to the roof of the house to recite some poetry. In his elation, Carl accidentally let go of Angela who fell from the roof. Angela realizes that, though she was unharmed, this is the reason why Carl left, to protect her. Angela weeps when she grasps that her father never stopped loving her.

Monica then reveals to Angela that she is an angel. Monica tells her that God does not want her to be afraid of love and commitment any longer. Angela believes she has ruined her chances of a life with Nick. Monica tells her that God will decide that, and, in that moment, Angela returns to the terrace of the New Year’s Eve party of the previous night. As the countdown to the New Year begins, Nick proposes to Angela and she joyfully accepts. The next morning, Angela and Nick drive to her childhood home, but are shocked to find an office building in its place. In a glass exhibit, they see the time capsule. Angela notices an old man waiting nearby, recognizes it to be Carl, and has a tearful reunion with her father as the angels watch happily.