The following version of this book was used to create the guide: Yanagihara, Hanya. To Paradise. Penguin Random House, 2022.

Hanya Yanagihara's novel To Paradise traces five protagonists' lives across three centuries in New York City. The novel employs a range of structural subversions, points of view, and temporal manipulations. The following summary adheres to the overarching structure of the novel, while relying upon the present tense.

In Book 1, "Washington Square," David lives in 1890s New York with his grandfather, Nathaniel Bingham, whom he calls Grandfather. David is unmarried, lives at his childhood Washington Square home, and works part time for Grandfather's charitable foundation. After Grandfather informs David and his siblings of what they will inherit following his death, David despairs. Grandfather plans on endowing him with Washington Square. Throughout his life, the house has been his refuge. Now that he knows the house will belong to him forever, David feels trapped.

One day, David arrives at the orphanage where he teaches part time to find the handsome music teacher, Edward, playing piano for his students. Immediately enamored, David is desperate to see him again. He manufactures a meeting, and the two spend an afternoon at Edward's squalid flat. Edward's humble lifestyle intrigues David. Unlike David, Edward is free. He life and home are simple, but he has the liberty to make his own decisions.

Over the course of the following weeks, David and Edward become increasingly intimate. Then Edward goes out of town. When Edward fails to write, David despairs. He throws himself into a relationship with the man Grandfather has chosen for him to marry. In the Free States society where David lives, same-sex marriage is acceptable and promoted. Yet David is disinterested in the man Grandfather has chosen for him. He offers stability, but what David wants is adventure and passion with Edward.

When Edward returns to town, he and David rekindle their relationship. Shortly thereafter, Grandfather reveals that his private investigator looked into Edward, revealing that Edward is a conman. Instead of heeding Grandfather’s warnings, David flees home and agrees to marry and run away to California with Edward. He knows he is taking a risk by abandoning his family and home. Yet the unknown with Edward offers the possibility of paradise.

In Book 2, Part 1, David resides in New York during the 1990s. He works as a paralegal at a legal firm where he meets and becomes involved with one of the partners, Charles. Although he eventually moves in with Charles, Charles refuses to acknowledge David at work. He does not want to upset the firm's power structure or reveal his homosexuality.

One night, Charles hosts a farewell party for his ex-boyfriend, Peter. Throughout the party, David is distracted. Earlier in the day, he received a letter he believes is about his father. Though he has yet to open the envelope its contents haunt David over the course of the evening. He cannot stop thinking about his father, and the ways in which his mistakes, abandonment, and weakness have influenced him throughout his life. David gradually realizes that his relationship with Charles is evidence that he is no different from his father.

In Book 2, Part 2, Wika writes to his son, David. His mother has recently informed him that David is living in New York. Because Wika assumes David resents him for his past mistakes, he hopes to clarify the past in order to earn David's forgiveness.

When David was a young boy, Wika reunited with his close childhood companion, Edward. The more time they spent together, the more intimate they became. Wika's involvement with Edward eventually kept him from discerning reality and truth for himself. One day, Edward brought Wika to Lipo-wao-nahele, a piece of property Wika inherited from his grandfather. Edward insisted it was the perfect place for them to create their utopian future together. Shortly after fleeing to Lipo-wao-nahele with David, the location lost its luster. David eventually left and abandoned Wika, for which Wika no longer blames him. He admits that he hurt and neglected his son, and hopes they can be reunited.

In Book 3, Charles, his partner, Nathaniel, and son, David, move from Hawaii to New York after Charles receives a job at the Department of New Diseases. Charles soon realizes that Nathaniel is unhappy. He also resents caring for David full time. Charles, however, is consumed by his work, and excited to contribute to society in a meaningful way.

Over the course of 30 years, he relays his life experiences, woes and fears, desires and longings not to his husband, but to his close friend Peter. These communications all take the form of letters. Over the years, Charles's and Nathaniel's marriage devolves. Nathaniel questions the integrity of Charles's work and feels angry with Charles for his inability to parent David. Eventually Nathaniel moves in with his friends, Aubrey and Norris.

After Aubrey and Norris die, Nathaniel inherits their home, where he ultimately begins raising David's daughter, Charlie. Charles later moves in to help. Then Nathaniel dies, and Charles assumes full custody of Charlie.

When Charlie falls ill, Charles agrees to give her a drug called Xychor. Though she survives the virus, Xychor alters Charlie's mental and emotional capacities.

Years after Charles's death, Charlie is living with her husband, Edward, in what was once Greenwich Village but has been renamed Zone Eight. In Zone Eight, Charlie's life is regulated by the state and federal governments. Charlie does not mind her life because it is predictable. Then one day she meets a man named David who begins to open her to the possibilities inside of her and beyond her insular world. When David reveals that he has been sent to Zone Eight by one of Charlie's grandfather's friends to rescue her, she is unsure what to believe. She is in love with David, but afraid to leave her home. Eventually she decides to risk her comfort in the pursuit of freedom and happiness.