I'd Like to Play Alone, Please Questions and Answers

This page provides 15 evidence-grounded questions and answers about Tom Segura's memoir I'd Like to Play Alone, Please (2022). Each answer is drawn directly from the book's chapters and explores key themes, character moments, and turning points.

Questions and Answers

1. Why does Tom's father often hang up or walk away mid-conversation?

Tom's father, Thomas N. Segura, a retired Marine captain, habitually ends conversations when he becomes bored. He once told Tom that he "gets bored and doesn't waste time" once he feels that way. This behavior was so consistent that Tom's college roommate Casey was convinced he had offended the father when the man simply walked away without excuse. The eccentricity foreshadows the chapter's poignant ending: days before his death, the father offered the simple wisdom that "the world goes on," a final, abrupt lesson in letting go. Read more about Thomas N. Segura.

2. What is Ellis's first complete sentence and what does it reveal about Tom?

Ellis, Tom's eldest son, looked directly at his father while drawing and said, "I'd like to play alone, please." Tom recognized the phrase as a perfect expression of his own need for solitude. He admits he loves to play alone and requires personal space, a trait his family has learned to accept. The moment became the book's title and a central theme of parenting and solitude. Explore the parenting themes.

3. Why does Tom panic after recommending his Netflix special to Serena Williams?

Tom told Serena Williams to watch his special Completely Normal after sitting next to her on a flight. Only afterward did he recall that the special includes a graphic stand‑up bit about a deadly threesome with Serena and Venus Williams. Months later at a party, a drunk Tom retells the entire embarrassing story to Serena and her husband Alexis Ohanian. Alexis laughs, but Serena politely suggests they get a drink. Tom promises never to bring it up again. See also celebrity encounters.

4. How does Dr. Drew Pinsky correct Tom's self-perception?

During an episode of Your Mom's House, Tom shows Dr. Drew disturbing internet clips. When Tom claims he enjoys "studying human behavior," Dr. Drew reframes it: "You like abnormal human behavior." Tom feels immediate shame, realizing his attraction to grotesque content is a personal quirk, not an academic interest. He then reflects on how he has always laughed uncontrollably at injury stories as a coping mechanism for discomfort. This moment ties into self-deprecating humor.

5. What is contradictory about Tom's mother's eating habits?

Tom's mother, a Peruvian immigrant with impeccable manners, constantly lectures others on health but subsists on a toddler‑like diet of buttered toast, pastries, chicken tenders, and fries — even at Michelin‑starred restaurants. Tom points out this hypocrisy and adds that his mother is famous for her long, loud farts, which he videotaped and posted online as payback for her relentless criticism. She remains unamused. Learn more about Tom's mother.

6. What was Comedy Central's reason for rejecting Tom's hour special?

In 2013, after a successful showcase at Flappers in Burbank, Comedy Central executives told Tom's manager that his set lacked a "theme." Tom was baffled, arguing that "the theme is funny jokes." The rejection forced him to accept a spec offer from Comedy Dynamics, eventually leading to Netflix picking up Completely Normal. Tom learned that waiting for permission is futile and urges artists to create their own opportunities. See the full book page.

7. How does Tom handle hate mail from a Louisiana woman?

After his Netflix special Disgraceful joked about building a wall around Louisiana, Tom was flooded with angry messages. He decided to have fun by pretending to be "Blake," his fictional assistant. In a Facebook exchange with a woman named Heather, Blake claimed Tom forced him to stay awake for three days over a coffee order. Heather sympathized, and Tom used the absurd ruse to build tolerance to criticism. This illustrates his growing acceptance of online hate as part of fame. See the identity and perception theme.

8. What is the function of the "Photo Essay" chapter?

Tom presents a childhood photograph and cites studies showing that seeing someone as a child makes it harder to be angry. He directly asks any upset reader to look at the picture and reconsider. This one‑page interlude uses humor to defuse potential frustration and reminds the audience of his playful persona. It reinforces the book's self‑deprecating tone. Connect to self-deprecating humor.

9. What are "Cherry Bombs" and "Sloppy Joes" in Tom's father's vocabulary?

Tom's father has created his own taxonomy for bowel movements, giving them nicknames such as "Sloppy Joes" (movements that fall out easily) and "Cherry Bombs" (messy ones that splatter). He discusses these categories openly, believing bowel movements are "criminally underappreciated." Tom's mother is always horrified, but Tom enjoys pointing out his father's grossness to provoke her hilarious reactions. This example captures the family dynamics in the Segura household.

10. Why does Tom's younger son Julian refuse to answer to his real name?

Julian, age three, has decided he no longer likes the name Julian and insists on being called invented names like Moth, Mr. Dog, Window, or "Red Light, Green Light, Yellow Light" (all three must be said). If anyone calls him Julian, he gets upset and corrects them. Tom finds this amusing yet challenging, and he jokingly admits that his son becomes "not favorite" when he rejects his name. Read about Julian.

11. How did the sexual fantasy bit about Serena and Venus originate?

In his stand‑up, Tom joked about a scenario where he dies in a threesome with Serena and Venus Williams involving a tennis racket. The bit was pure exaggeration for comedic effect. When Tom met Serena on a flight and recommended his special, he had completely forgotten that joke. Months later, at a party, he drunkenly retold the entire incident to Serena and her husband, painfully aware of the gap between stage fantasy and real life.

12. Why does Tom laugh at personal injury stories?

Tom admits he uncontrollably laughs when someone tells him an injury story, such as a construction coworker's bizarre accident. He believes this is his way of processing discomfort — as a child he would squirm at gory details, and eventually the squirming turned into laughter. This same reaction drives his enjoyment of showing guests disturbing clips on his podcast. It is a prime example of his self-deprecating humor.

13. What lesson does Tom draw from the Comedy Central rejection?

Comedy Central rejected Tom's first hour special for lacking a theme, so he independently shot Completely Normal with Comedy Dynamics. When Netflix made an offer — then considered a letdown compared to HBO — Tom realized that artists must take action rather than wait for permission. The chapter ends with a sincere call to create your own opportunities. This lesson is a key part of the book's conclusion. See the ending explained.

14. What does Tom's fake assistant Blake reveal about dealing with criticism?

In the Facebook exchange with a Louisiana woman, Tom (as Blake) claims that Tom Segura forced him to stay awake for three days for bringing an iced coffee with too little ice. The woman commiserates, thinking Tom is a monster. By crafting this absurd narrative, Tom turns online hate into comedy and gradually builds tolerance to what he calls "snake venom." It shows how he transforms criticism into material.

15. What final wisdom does Tom's father share before dying?

Days before his death, Tom's father asked if Tom knew what happens after someone dies. When Tom said no, his father replied, "The world goes on." This succinct statement encapsulates the father's pragmatic, unsentimental worldview and provides closure after a lifetime of eccentric behavior — the phone hang‑ups, war stories, and graphic bathroom talk. It is a quiet, powerful ending to a chapter filled with chaos.