The Five People You Meet in Heaven begins on the last day of Eddie's life. He is 83 years old and works as the maintenance manager at Ruby Pier amusement park, the same job his father once held. Eddie is resigned to his position, even though he swore to never follow in his father's footsteps. Most of the people he loved have passed away and the knee injury he sustained during World War II still plagues his every movement. However, Eddie is beloved at Ruby Pier; his co-worker Dominguez and the visiting children can see through his prickly exterior. Eddie is proud of Ruby Pier's spotless safety record, but that all changes when a missing car key damages the machinery on a ride called “Freddy's Free Fall.” Screaming patrons are stranded, dangling in the air as the cart threatens to fall off the track. Moving as quickly as he can, Eddie tries to save a young girl from being crushed by the falling cart. He remembers grasping her small hand and then - his life is over.
Mitch Albom constructs the remaining sections of this novel by alternating between Eddie's present-tense encounters in Heaven and flashbacks to Eddie's various birthdays. Eddie's first stop in Heaven is Ruby Pier, 75 years before the day he died. All of his mortal aches and pains seem to have disappeared. It is here that Eddie meets the Blue Man, who was part of the Ruby Pier sideshow when Eddie was eight years old. The Blue Man reveals to Eddie that he was responsible for the Blue Man's death. Young Eddie dashed in front of the Blue Man’s car chasing a runaway baseball, and the Blue Man's rattled nerves led him into a car accident that eventually killed him. Eddie asks the Blue Man if the little girl he tried to save from the falling ride actually survived, but his companion gives no response. The Blue Man finally tells Eddie that he must meet four more people before he can continue on his journey into the afterlife.
Eddie’s surroundings change and he finds himself in the scorched earth of war. Here, Eddie meets the second of his "Five People": the commanding officer of his World War II platoon, whom he calls Captain. Eddie recalls being held captive by enemy soldiers for many months, along with the Captain and four others. We learn that Eddie was responsible for devising the plan that enabled the Americans' escape. In the aftermath, the Captain commanded Eddie and the other soldiers to torch the supposedly empty village under which they had been imprisoned. While the others prepared to outrun the blaze, Eddie raced into a burning tent because he thought there was a child trapped inside. However, a bullet shattered his knee, stopping him in his tracks. Eddie learns about the importance of sacrifice from the Captain, who admits to being the guilty of shooting Eddie. The Captain explains that Eddie had to sacrifice his knee to save his life. The Captain then reveals that he died after stepping on a landmine while trying to get Eddie to safety - so he made a sacrifice as well. The Captain is at peace with his sacrifice and advises Eddie to let go of his anger.
Next, Eddie finds himself outside of a diner filled with various people from different eras and walks of life. Through the window, Eddie recognizes one of the patrons - his father. Eddie tries to get the old man's attention, but Eddie's father cannot hear his son. Eddie has flashbacks of the abuse he suffered at his alcoholic father's hands. Then, Eddie meets Ruby - the third of his "Five People." Ruby reveals that her husband Emile was the founder of Ruby Pier, which he named after his beloved wife. Ruby offers Eddie a new perspective on the circumstances surrounding his father's death. Eddie used to think that his father caught pneumonia after making a drunken decision to jump into the freezing ocean. However, it turns out that Eddie's father was saving the life of his oldest friend, Mickey Shea. Mickey took a suicidal jump into the ocean after Eddie's father caught him assaulting Eddie's mother, but even so, Eddie's father could not let his friend drown. Eddie's father had many faults, Ruby explains, but he was loyal. She tells Eddie that his father called to his family out the hospital window right before his death. Ruby knows this because she was tending to Emile in the very same room.
After Eddie's father died, Eddie and his new wife, Marguerite, had to move in with Eddie's mother in order to look after her. Eddie took on his father's old job at Ruby Pier. Eddie remembers resenting his father for dying because it led to Eddie spending his life at Ruby Pier, a place he desperately wanted to escape. However, Ruby shows Eddie that his anger brought him much more pain than his father's neglect and abuse, and advises him to let go. Eddie heeds Ruby's advice. He is finally able to break through his emotional walls and forgive the man he spent so much of his life hating.
Eddie's next encounter leads him through room after room of wedding receptions from many different cultures. At the final ceremony, Eddie recognizes the beautiful Italian bridesmaid - his beloved wife, Marguerite. Marguerite was the love of Eddie's life; they met on Ruby Pier as teenagers. They suffered through a number of struggles after Eddie's return from war. They had to move into Eddie's mother's apartment building after Eddie's father's death. Then, they found out that they were unable to have children. They finally saved up enough money to adopt, but Eddie incited Marguerite's ire by gambling some of it away at the racetrack on his 39th birthday. They fought. Marguerite felt bad for fighting on Eddie's birthday and drove to the racetrack to apologize, but she got into a terrible automobile accident. Although Marguerite recovered, her medical bills sapped the rest of their savings. Tension lingered between the spouses for a long time, but they eventually grew back together. Eddie was devastated when Marguerite died of a brain tumor at the age of 56. Marguerite is the fourth of Eddie's "Five People," and she is there to teach him about eternal love. She shows him that their love was always there, even after she died.
Eddie's fifth and final meeting is with a young girl named Tala with distinctly Filipino features. Tala reveals that she was the child Eddie saw in the burning tent in the Philippines, and she died that day. Eddie falls apart upon realizing that he was responsible for this young girl's painful and untimely death, but Tala comforts him. She asks Eddie to wash her back with a smooth stone, like her mother used to do, and Eddie takes on this parental task. Tala asks Eddie why he was so unhappy on earth, and Eddie responds that he never did anything meaningful in his life. Tala rejects his assessment and tells him that he was meant to be at Ruby Pier to keep all the children safe on the rides. She also reveals that Eddie did save the little girl from the falling ride on the day of his death - he pushed her out of the way; the hands he felt were Tala's as she brought him to Heaven. Eddie watches as Tala's scars and burns melt away under the smooth stone. Finally, Eddie is able to release all of the demons that plagued his earthly life. He is finally transported back to his beloved Marguerite, with whom he will spend eternity.