Rose Collins, portrayed by Susan Sarandon, unexpectedly encounters an old high school friend while out shopping in the bustling streets of New York City during the holiday season. Their brief conversation reveals Rose’s marital status and her large family, but it’s evident that there’s an underlying discomfort as she quickly bids farewell. Soon after, we find Rose entering a hospital, where she heads down a corridor to visit her mother, Helen (Una Kay), who is in a state of advanced Alzheimer’s, vacantly sitting in bed. In a touching gesture, Rose brings Helen some thoughtful gifts and gazes into another room, noticing a lonely, comatose patient. Driven by compassion, she decides to spruce up the stark space by hanging an angel figurine on the window. Just then, she meets a visitor named Charlie Boyd, depicted by Robin Williams, who is lingering by the doorway. They exchange polite but awkward greetings before Rose hastily makes her exit.

Meanwhile, a New York police officer named Mike Riley, played by Paul Walker, spots a captivating woman named Nina, brought to life by Penélope Cruz, walking along the sidewalk. Their subsequent interaction reveals a history between them; they are actually engaged fiancés eagerly preparing for their upcoming wedding.

As the narrative unfolds, we see Rose at her workplace. Through the banter with her assistant, we glean details about her strained life—she is divorced, her father has passed away, her sister is missing out on Christmas this year, and she has been a dedicated caregiver for the last decade to her mother. Her assistant humorously suggests that Rose “needs to get laid,” and it is revealed that a younger coworker, Marco (Daniel Sunjata), has developed feelings for her. Despite initial disbelief due to their age difference, Rose reluctantly agrees to go on a date with him.

On the personal front, Mike drops Nina off at her job, only to later witness her embracing another man, which sends him spiraling into a fit of jealousy. He automatically assumes the worst, leading to misunderstandings that test their relationship.

In another scene, Jules Calvert (Marcus Thomas) holds a conversation in a diner with his friend Glenn (Merwin Mondisir) about one of his fondest memories during Christmas, an event that occurred in the hospital. Amid their chatter, Jules faces issues with debts, further complicating his holiday cheer.

Mike joins his partner Dennis (Sonny Marinelli) at the same diner, where an elderly waiter named Artie (Alan Arkin) shows undue familiarity and affection towards Mike, leading to an uncomfortable situation. Meanwhile, in Rose’s world, her date with Marco flounders when he makes advances that leave her feeling uneasy, ultimately leading her to ask him to leave.

As Nina decorates a Christmas tree with her male friend back at their apartment, a misunderstanding causes Mike to erupt in jealousy, resulting in a wrecked Christmas scene. In contrast, Rose wanders the streets feeling dejected and stumbles upon a festive gathering, intrigued by the love and warmth that radiates within the decorated house. She confronts Nina, who is in tears over her unexpected pregnancy, causing a deepened bond between the two women.

Mike navigates his growing frustrations as he grapples with jealousy, while Rose finds solace in encouraging Nina to embrace true love, leading to poignant moments throughout both characters’ arcs. As significant life events culminate, Rose steps into an open-mic contest that unexpectedly reveals her deeper grief regarding her past. The crowd’s sympathy helps her win a small Christmas tree, symbolizing hope amidst her sorrow.

As the story progresses, the paths of these characters intertwine with revelations, allowing for both emotional and physical healing. With exhibitions of vulnerability, they confront their pasts and what they desire for their futures. Charlie’s unexpectedly insightful conversation with Rose unveils deep truths about life, love, and moving on, while Mike’s confrontations with Artie forge new understandings of forgiveness and the impacts of past relationships.

In a series of touching moments, Rose finds herself back at the hospital, contemplating her mother’s well-being once more. A significant twist reveals profound connections between her experiences and Charlie’s past, leading to a heartwarming conclusion that underscores the themes of forgiveness, love, and the steps towards healing.

Ultimately, through intertwining lives alongside heartfelt performances from Susan Sarandon and Penélope Cruz, this film explores the complexities of love, grief, and the miracle of second chances during one of the most emotionally charged seasons of the year.