The film has several intertwined plot lines: One story is about a driven, workaholic lawyer named Robert Layton and the impact of his job on his marriage to Kate, and to his relationship with his daughter Lily. Another is about Robert's mother Ellen, and her friendly neighbor Dalton who is a teacher at Nathan and Lily's school. The main story is about Maggie Andrews and her terminal illness, and how her family (small businessman husband Jack and young son Nathan) deals with the impending loss. All stories are linked together. The story opens with Robert visiting the cemetery shortly before Christmas. He sees a younger man wearing a Boston Red Sox Cap visiting another grave. We flash back...
Robert is leaving his office and notices a delivery truck driving away. He sees that a box has fallen out of the back of the truck and opens up the box to find a pair of red brocade shoes with gold trim. After repeatedly failing to remember to take the shoes to Wilsons Store, Robert finally returns the shoes to Tom Wilson, the owner of Wilsons. Outside the store, Robert's car won't start and Tom tells him about a great repair shop run by Jack. Next, we see an increasingly tired Maggie and eventually learn that she has congestive heart failure due to a virus and is now in need of a transplant. As Maggie gets weaker, Kate takes over Maggie's volunteer job directing the local school choir during the Christmas season.
One day, Nathan overhears his mother telling Kate how she and Jack met at a dance studio, and how every year on their anniversary they would to go dancing. Nathan now knows that he wants to get his mom a very special pair of dancing shoes for Christmas. He goes to Wilsons store and finds a beautiful pair of red Christmas shoes he just knows his mom will love...the same shoes Robert returned to Wilsons store. Nathan set out to save the money to buy the shoes by collecting soda pop cans after his dad tells him each is worth a nickel. Dalton helps care for Nathan after school and takes him to meet his neighbor Ellen. Ellen gives Nathan her son's old Red Sox Cap. She then takes Robert's old lunch box and writes Robert a note to place inside.
Maggie does not receive her heart transplant because the heart was tested to have Hepatitis B. By the time they find another heart she will be too ill to undergo the operation. Maggie decides to go home to die. Ellen sees Dalton loading large bags filled with empty soda pop cans into his trunk. Ellen tells Dalton that she is going to leave the outside Christmas light on for a while. The next morning the lights are still on and Dalton discovers that Ellen has died. Later when Dalton is walking with Nathan, he tells Nathan that his wife died 11 years ago. He tells Nathan to cross over to an alley, where Nathan finds a large number of empty soda pop cans.
On Christmas Eve, while Maggie is home in her bed dying. Nathan runs out of the house to Wilson's Department Store - only to find the door locked. Robert is late, as usual, going to Wilson's to pick up gifts for his wife and daughter. Together they get the store clerk to open the door, which we find out "sometimes locks itself". When Nathan runs to the counter in front of Robert to pay for the shoes, the very rude clerk tells him he does not have enough money to pay for them. Robert standing behind him overhears the clerk tell Nathan he does not have enough money to buy the shoes and sees Nathan get very upset. Robert asks Nathan what is going on. Nathan explains that he wants the shoes for his mom, for whom this will be her last Christmas, so that she will be beautiful in heaven. After hearing the story, Robert pays the balance of the money needed. Nathan thanks Robert, and runs all the way back to his house.
Robert leaves the store without the gifts, realizing that being with his family is the greatest gift he can give them. His car won't start again and asks Tom Wilson to give him a ride. Tom asks him if he is going to the Christmas concert. Robert says yes and Tom tells him it is at a new location. Meanwhile, Nathan gives his mom the shoes. She says they are the most beautiful shoes she has ever seen. Robert and Tom arrive at the new location for the Christmas concert and meet Kate and Lily. The concert is in front of the Andrews home where they are caroling for Maggie. After the vigil, a group of Robert's clients thank Robert for all he is doing for them and giving them hope at Christmas. Robert and Kate reconcile.
The family sees the light go off in Maggie's room.
Later, Robert sees the package his mom Ellen had sent, and reads the note inside. She would be happy to know he is making time for his family just as she wanted for Robert.
We flash forward to present time at the cemetery. Robert tells the younger man that he likes his Boston Red Sox Cap. After the younger man leaves, Robert sees the red shoes on the grave the young man was visiting. He realizes who he is and calls after him, but he has already driven off.
Robert smiles to himself, and heads back to his car.Rob Lowe as Robert Layton
Kimberly Williams as Maggie Elizabeth Andrews
Max Morrow as Nathan Andrews
Maria del Mar as Kate Layton
Dorian Harewood as Dalton Gregory
Shirley Douglas as Ellen G. Layton
Amber Marshall as Lilly Layton
Jeremy Akerman as Tom Wilson