Samantha Irby’s feelings of failure and inadequacy are a major subject of the book, and yet by many people’s standards she is a great success—an award-winning author, a writer on numerous popular television shows, and more. How do you make sense of this apparent contradiction, and how has Irby’s self-deprecating style contributed to her success?

Irby gives detailed descriptions of the music she loved from her days as an early adolescent, noting that she still has those recordings and wishes to share them with her readers. What impact did music have in her life? Why did she find it so important?

In her essay “Love and Marriage,” Irby says that there is no one true love for each soul, that this is a myth propagated by “romantic comedies.” Is this observation realistic, an intentionally humorous comment, or perhaps cynicism? What in her own life prompts Irby to hold this position?