The following version of the book was used to create this study guide: Sedaris, David. Calypso. Little, Brown and Company, 2018. First Hardcover Edition.

For David Sedaris, the only perk of being middle-aged is that he has now acquired a proper guest room. The first essay in this collection, "Company Man," discusses David and his partner Hugh's experiences as hosts, with a particular emphasis on when three of David's sisters come to visit them at their home in Sussex for Christmas 2012. This is an important visit for David as they are all getting older and he wonders how many more times they will be able to do something like this all together.

The following essay, "Now We Are Five," is about the death of David's youngest sister Tiffany, who committed suicide in May 2013. Not long after, the family reunites on Emerald Isle, North Carolina, where they used to holiday as children every year, but where they have not been since their mother died many years ago. This time, David fulfills a childhood dream of owning a beach house there, and the family makes plans to spend time there together regularly.

The third essay, "Little Guy," is about David's experiences as a short man.

The fourth essay, "Stepping Out," is about David's obsession with walking and his Fitbit.

In the fifth essay, "A House Divided," the Sedaris family reunites on Emerald Isle for Thanksgiving, where David reflects on class, poverty, and how those factors shaped the life of his sister Tiffany in particular.

The next essay, "The Perfect Fit," takes David and two of his sisters to Tokyo where they indulge in their shared love of shopping, something that Hugh and his family cannot fully understand.

Back on Emerald Isle in the following essay, "Leviathan," David reflects on aging, politics, and his relationship with his father.

In the eighth essay, "Your English Is So Good," David writes a humorous English guide for business travelers to the United States. In it, he challenges the ubiquitousness of common stock phrases and expresses his desire for more authentic conversations with strangers and service people.

In the essay "Calypso," after going to the doctor for the first time in a while, David is told he has a lipoma: a harmless fatty tumor. He wants to get it removed and feed it to a snapping turtle on Emerald Isle but the surgeon says that it is illegal for him to give his patents anything he removes from their bodies. Instead, David leaves the tumor intact until he meets a woman who offers to remove it privately and let him keep it. He agrees and freezes the lipoma in anticipation of his next trip to Emerald Isle.

The next essay is "A Modest Proposal." Back home in Sussex, David waits for news on whether or not the U.S. Supreme Court will legalize gay marriage. He is delighted when it is legalized, even though he himself does not want to get married. However, after realizing the financial benefits of getting married, he persists in trying to convince a reluctant Hugh that it is the right thing to do, for purely practical and financial reasons.

In the essay "The Silent Treatment," David writes about his relationship with his father, and the difficulty they have always had in connecting and making conversation, with the exception of when they listen to jazz music together.

At home in Sussex in the following piece, "Untamed," David befriends a fox who he names Carol.

In the next essay, "The One(s) Who Got Away," David asks Hugh how many sexual partners he had before they got together and is annoyed by the high number.

In the next essay, "Sorry," the family returns to Emerald Isle where differences between the Sedaris family and Hugh's family become clear and cause tension. David feeds his lipoma to a turtle, though the original turtle he had wanted to feed it too had since died.

In the essay "Boo-Hooey," David writes about his mother and Tiffany visiting him in his dreams, though he does not like talking about ghosts.

The following essay, "A Number of Reasons I've Been Depressed Lately," covers ten points that have been upsetting David, all related to the 2016 U.S. presidential election.

"Why Aren't You Laughing?" is about David's mother and her struggles with alcoholism.

The next piece, "I'm Still Standing," takes an entirely different tone as David recounts the trials and tribulations of suffering from a gastrointestinal virus while on tour.

"The Spirit World" returns to the subject of David's mom and Tiffany when his sister Amy visits a psychic and shares her experiences of talking to their deceased family members.

The penultimate essay,, "And While You're Up There, Check On My Prostate," includes a series of curse phrases that David has collected from different countries around the world throughout his travels and which are all quite humorous when translated to English.

In the final essay, "The Comey Memo," David visits his father's home and reflects on the realities of aging and his relationship with his father.