Sitting in front of a typewriter, Danny Morgan thinks back to growing up on the north side of Chicago, Illinois, and being a member of “The Rogues.” Inspired by movie heroes like Errol Flynn, the boys in the club were determined to have adventures and meet girls, while dreaming of making an impact on the world. Danny yearned to be a writer, and his best friend Sol wanted to be a pirate. As adults, the seven members of the group who still live in Chicago spend time together and play football on Sunday. Danny makes a living as a mailman and remains an aspiring writer, but misses the idealism of the youthful Rogues. He worries that he has become stuck in life, and those feelings of invincibility and adventure are now foreign to him. Sol, however, continues to be a starry-eyed romantic and optimist, despite being hospitalized with a life-threatening illness. Meanwhile, Danny is heartbroken that his ex-girlfriend, Emily Rubens, plans to marry a successful businessman. Danny remembers when he and Emily first met on her front porch, as he was delivering mail, and how they struggled to leave the bed during the beginning of their affair. When Sol is released from the hospital, Danny and the other Rogues hang out at his apartment and drink beer. Sol complains about their losing football record and says he is ready to play again, thanks to his new medication. After everyone leaves, Sol implores Danny to telephone Emily and reveal his feelings. Even though she is getting married on Sunday, Sol reminds Danny about the romantic scene from the film The Graduate, in which the character “Benjamin” interrupts “Elaine’s” wedding. Danny, however, does not have Sol’s confidence, and simply stands outside Emily’s apartment, watching her through the window. He remembers when Emily suggested they get married and start a family, but he did not feel ready and wanted to finish writing his book first. Later, Sol rents a limousine with a driver and convinces Danny to join him for a night of carousing. Cruising around town, they cajole the other Rogues, Mickey, Pete, Marty, Eddy, and Bobby, away from their work and family obligations. Inspired to be college sophomores again, the seven friends drink and dance at a university party. At sunrise, Sol leads the Rogues and several hangers-on to the shore of Lake Michigan where they watch a tall sailing ship. Sol declares they are going to the Caribbean island of Tortuga, but as the rollicking group rows a boat toward the schooner, Sol feels unwell and the Rogues rush him back to the hospital. Danny reveals to Mickey that the story about a “new medication” was a fabrication to help them cope with Sol dying. Meanwhile, Danny thinks back to an argument he had with Emily as she encouraged him to write, and he shouted that he was not capable of telling stories. When a stray dog continues to linger outside his apartment building, Danny brings the canine to the animal shelter where Emily works and charms her into accepting the mutt. Danny invites her to a Halloween party that evening and says she can bring her fiancé. When he declares that he misses their conversations, Emily agrees that they were a great couple, but wonders if they tried too hard to make the relationship work. At the hospital, Danny becomes emotional at the thought of losing his friend, and Sol tries to reassure him, while admitting he hates the idea of dying in a hospital, calling it “unheroic.” After the visit, Danny attempts to convince the other Rogues to help fulfill Sol’s pirate dream of sailing away on a boat. His friends, who have busy lives, are reluctant. At the Halloween party, Danny watches as Emily and her fiancé arrive, but he keeps his distance, waiting for the right moment to approach her. Emily looks for him in the crowd and appears disappointed when she cannot find him. When she enters the bathroom, Danny follows, locks the door and they kiss. Afterward, an exuberant Danny tells Sol about the encounter, and his friend is hopeful about a last-minute reconciliation before the wedding. The following day, Danny goes to Emily’s house and declares she is marrying the wrong guy, but Emily is not as convinced and tells Danny he should leave. On Sunday, the Rogues gather in the park for the weekly football game, which Danny believes might be their last one if Sol is not around to motivate them. During the match, Danny tries to persuade his friends to reconsider the sailboat idea and reminds them of Sol’s generosity over the years, but they still appear unwilling. The Rogues struggle throughout the game, and on the final play a downpour occurs, the team is defeated and the friends go their separate ways. Afterward, Danny drives to Emily’s house and pounds on the door. When no one answers, he speeds to the wedding on the other side of town. As he gets caught waiting for a drawbridge, he abandons his car, leaps over the opening drawbridge, and plunges into the Chicago River. After swimming to shore, Danny runs through the streets, but arrives too late to the ceremony as he hears the bride and groom announced for the first dance. Dejected, he slowly walks back and rests on a park bench outside Sol’s hospital. Later, Marty knocks on Danny’s door and introduces Bull Martin, the captain of a tall sailing ship. Danny picks up Sol from the hospital and announces they are going to Tortuga. They rendezvous with the other Rogues at the dock, and as they set sail, Captain Martin allows Sol to pilot the boat. On the ninth day of the voyage, Sol dies. After his passing, the friends become preoccupied with changes in their lives and see less of each other. Sometime later, Emily gets a divorce and moves back to Chicago. One day, Danny encounters her at a supermarket, and she is holding his recently-published novel, All the Sad Young Men. As they walk in the park, Danny tells Emily that the book is about a man who believes in happy endings.