The narrative jumps back in time by 20 years to Murray McBride’s 100th birthday. It is 1997. Murray has grown tired of life, primarily because his wife, Jenny, died 18 months ago. Each morning, he takes one pill, without which his lungs would fill with fluid and he would die. Otherwise, he is remarkably healthy for his age. Murray visits his doctor, Dr. Keaton, for his annual physical exam. He jokes that he is going to stop taking his pill on the 22nd of that month. His doctor worries about his unwillingness to socialize outside of occasional modeling work for advertisements. He suggests that Murray model for a local life drawing class and emphasizes how important it is for Murray to find a reason to live, or else he is “going to die a pathetic old man” (22).

Murray considers his doctor’s suggestion but decides it is time for him to die. He will not take his pill the next morning, so today will be his last day on earth. He decides to visit the hospital to volunteer or do a good deed. He goes to the cardiac ward, where a young boy, Jason, is playing a video game. Jason invites Murray to play with him, but Murray cannot understand the technology. He objects to Jason’s insistence on calling him “dude” and cursing. Jason often has to stop to breathe from an oxygen mask; he is 10 years old, but he looks younger because he is sick. After a few minutes, Jason’s father arrives and hurries him away. Jason protests—he has left something behind and wants to get it back—but his father does not listen. Murray finds what Jason was looking for; it’s a small piece of paper on which he has written the following:

Five Things I want to do Before My Heart Dies and I go to Heaven

1. Kiss a girl (on the lips)

2. Hit a home run in a major league baseball stadium

3. Be a Superhero

4. Find a Nice Boyfriend for Mom

5. Do real magic (36).

Murray is moved by the list and decides he has to help Jason accomplish his goals. He now has a reason to keep living.

Murray’s grandson, Chance, visits unexpectedly. Murray resents Chance, who always appears to be coveting Murray’s baseball paraphernalia from the days when he played for the Chicago Cubs. Chance, who has been married three times, wants Murray to move into an old age home; Murray refuses. Chance gives him an email machine to help him keep up with a changing world, but Murray takes offense at the gift. He asks Chance to leave, but he wishes he could tell his grandson he loves him instead of shutting him out. He dumps the email machine in the garbage.

Still feeling guilty about his interaction with Chance, Murray goes to church. He meets his priest, Father James, and explains his desire to help Jason with his wishes. Father James agrees to help Murray get in touch with Jason; he calls the hospital and asks for Jason’s email address. He then patiently helps Murray compose an email to Jason even though Murray struggles to understand how email works. Jason responds almost immediately, pleased that he will soon get his list back. Murray goes home, feeling hopeful for the first time in a while.

Murray decides to attend the life-drawing class that his doctor suggested. He sometimes does modeling work for advertisements, but he dislikes it because it reminds him of how old he is and how much he misses being young. When he arrives at the class, he immediately feels uncomfortable: The room is full of incense and candles, and the instructor expects him to take off all his clothes. He refuses and removes only his shirt. A young man sits next to him as a hand model, and the two get along. During the class, the instructor emphasizes how old Murray looks. Dejected, he returns home.

At home, Murray retrieves the email machine from the trash, but he cannot get it to work. Father James calls: He has found a way for Murray to meet with Jason. He picks Murray up and brings him to the hospital. There, Murray meets with Jason’s health advocate, who agrees to let Murray act as Jason’s brother in the Big Brothers mentorship program. On the way home, Murray admits that he cannot use the email machine. Father James agrees to send a teenager from his congregation over to help. The teenager arrives a couple of hours later and reluctantly helps Murray set up the machine. Murray and Jason exchange several emails. Murray repeatedly asks Jason to use more formal language and to call him “Mr. McBride.”

It has been many years since Murray has driven his car. He no longer has a license, but he decides to drive to Jason’s father’s house anyway. He goes very slowly and struggles to control the car. He arrives at a mansion. When Jason’s father opens the door, he is in the middle of a phone call. Because he doesn’t understand how cell phones work, Murray assumes Jason’s father is talking to him and gets very confused. Eventually, he comes inside and finds Jason playing video games again. Although he is once again irritated by Jason’s informal speech—he calls Murray “Mr. Bro” instead of “sir”—he asks if Jason would like to visit a baseball stadium.

At the stadium, Jason tells Murray about his illness: He needs a heart transplant, and without one, he will soon die. When they talk about baseball, Jason is surprised by how much Murray knows; Murray does not tell him that he used to play professionally. Murray returns Jason’s list, and they discuss the five wishes. Murray agrees to help Jason kiss a girl on the lips even though he finds the prospect somewhat inappropriate. Mindy Applegate, a high school cheerleader, is the most attractive girl Jason has ever seen. Murray formulates a plan to help Jason kiss her.

Murray drives Jason to Chance’s house. He asks his grandson to come with them on a brief reconnaissance mission to prepare for the kiss. He also thanks Chance for the email machine. Murray is feeling young again, and he wants to share that positive feeling with his grandson. Chance responds poorly, refusing to join the reconnaissance mission and criticizing Murray for driving without a license. He does not like children.