Greetings Book Clubs!

A full book club kit is coming soon, but in the meantime, consider the following discussion questions for your book club discussion of How to Fail at Flirting plus a bonus cocktail recipe, perfect for reading or discussing.
  • 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?
  • 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?
  • Naya shares with Jake that she's had lackluster sexual experiences with other men and not felt comfortable asking for what she wanted. Do you think that's a common experience for women and why?
  • 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?
  • 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?
  • While Aaron and Felicia are somewhat meddling and Tyson and Eric tease, what role do Jake and Naya's friends play in encouraging healthy relationships?
  • 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?
  • 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?
  • 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?

How To Fail at Flirting Cocktail: Persimmon 75

Image of cocktailPhoto & Recipe by Allison Jessing
  • 1 oz gin
  • .75 oz Elderflower liqueur 
  • 1 oz Persimmon Simple Syrup (recipe below) 
  • 3 oz Prosecco or other dry sparkling wine 
  • Cinnamon sugar for rim of the glass (Optional) 
  • Edible flowers or Cinnamon stick, for garnish (optional) 
 
Wet the rim of a champagne coupe with water and roll gently in cinnamon sugar. Combine gin, elderflower, and simple syrup in a cocktail shaker packed with ice, and shake 15-20 seconds, or until exterior of the shaker is frosty. Strain into the sugared coupe. Gently top with 3 oz. of sparkling wine, stir gently, and garnish with an edible flower or a cinnamon stick. 
 
Persimmon Simple Syrup
Yields 1 cup of syrup 
.5 cup water
.5 cup granulated sugar
1 cinnamon stick, roughly 3” 
.5 chopped fuyu persimmon, very ripe*
.5 tsp vanilla extract 
*If persimmons are out of season or you just can’t find them, an equal amount of peach or nectarine will also work well in this recipe.
 
Mix water and sugar in a saucepan. Bring to a boil until sugar is dissolved. Stir in the cinnamon stick, chopped persimmon, and vanilla extract. Simmer over low heat for 10 minutes. The fruit should be very soft, to the point of dissolving. Remove from heat and allow to cool. Once cooled, strain the syrup to remove the cinnamon stick and remaining fruit pulp. 
 
This syrup keeps up to 2 weeks in a sealed container in the refrigerator. Use any leftovers in your tea!