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1. What elements of Shteyngart’s dystopian near-future do you see in our contemporary world?
2. In that same vein, do you feel that we really are in, or are headed for, a post-literate age? Have a media-saturated environment and short attention spans affected our ability to read and appreciate books?
3. Lenny and Eunice come from two opposing cultures and have different ethnic backgrounds. While he is a ruminative book reader, hers is the generation of the instant and fleeting. For all their differences, why do you think Lenny and Eunice are drawn together? What do they share in common in terms of their personal history?
4. After a trip home to Long Island, Lenny contemplates an existence that is “at the end of the busted rainbow, at the end of the day, at the end of the empire.” What does he mean by this? Do you feel that we are at the end of an era?
5. Lenny’s employer, Post Human Services, offers the promise of life extension for High Net Worth individuals. How do you think losing the assurance of death, a great equalizer, would affect the dynamic of society? If you had the option, would you seek out immortality?
6. Super Sad True Love Story is an epistolary novel—one written as a series of documents. Discuss the how Shteyngart’s use of diary entries and digital exchanges impacted your reading experience.
7. One target of Shteyngart’s satire is the value placed on youthfulness. Discuss how this preoccupation manifests itself in the novel—consider Eunice’s relationship with Lenny and Joshie, The Post Human Services, and representations of the elderly.
8. Lenny has been described as a twentieth century man in a twenty-first century world. How, specifically, is he anachronistic to the “new” New York?
9. Shteyngart includes elements of science fiction, romance, and dystopian fantasy. How do you think each of these genres manifests itself in the novel? Why is each important?
10. Super Sad True Love Story treads into dark territory—mortality, heartbreak, the demise of a culture—yet, as a satire, it relies heavily on humor for its social criticism. In your opinion, how important is humor in evaluating and responding to the world in which we live?
11. Though Super Sad True Love Story is set in the (very near) future, there is a strong immigrant presence that also harkens back to the American past. Discuss the portrayal and significance of immigrants in the novel.
12. In the Super Sad universe, there is no such thing as a private detail. In our world, what do you feel are the benefits and pitfalls of social media? Where should we draw the line in terms of what we broadcast about our personal lives?