Book Club Discussion Questions and Guide for How to Fail at Flirting by Denise Williams

1. Naya begins the book feeling she's in a rut after closing herself off for so many years. Did Naya's list make you think of what you could add to your own to-do list?
2. Naya shares with Jake that she's had lackluster sexual experiences with other men and has not felt comfortable asking for what she wanted. Do you think that's a common experience for women? Why?
3. Jake goes with Naya on TILT and the Ferris wheel despite his fear of heights. Is there a fear you'd be willing to confront to be near someone?
4. Naya finds it hard to disclose her past trauma to Jake. Why do you think this is, and what makes her ultimately feel she can trust him?
5. As a professor, Naya discusses some of the challenges of her work. Do any parts of Naya's story challenge commonly held beliefs about universities and professors?
6. While Aaron and Felicia are somewhat meddling and Tyson and Eric tease, what role do Jake's and Naya's friends play in encouraging healthy relationships?
7. Naya appreciates that Jake is a "hot nerd" who lacks the arrogance and posturing of her ex. What about a cinnamon roll or non-alpha hero is appealing or off-putting to you?
8. Naya checks off many items on her list throughout the book. Was there one item or moment of growth that stood out to you as the most meaningful? Did it speak to your own experiences?
9. Jake and Naya's relationship begins with the botched one-night stand and remains physical. What is Naya able to communicate through physical intimacy that she wasn't able or willing to verbalize?

Unless otherwise stated, this discussion guide is reprinted with the permission of Berkley Books. Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.