READERS GUIDE
Discussion Guide1. Winging It with You makes for the perfect armchair travel as we are vicariously flown across the globe to some of the most vibrant destinations. Which of the locations en route Theo and Asher’s journey on The Epic Trek would you put at the top of your travel bucket list and why?
2. Winging It with You features the ever popular fake-dating trope. Discuss to what extent this trope best fosters intimacy between Asher and Theo over other possible romance tropes, especially within the setup of this competition. Put simply: In the battle of tropes, which one wins out?
3. Asher and Theo engage in an emotional game of tug-of-war. At what point did you observe either one of them fully giving in to their feelings, and what was the discerning quality that gave them away? Discuss to what extent the story being told through both perspectives clarified your understanding of where the couple stood at each moment.
4. Theo and Asher have their bags packed, both literally and metaphorically, as it relates to their emotional baggage. Discuss how Theo and Asher each hold themselves back in love and in life. In your experience, what does it often take to open yourself up again, to unpack your bags if you will?
5. In writing this book, author Chip Pons was intentional to illustrate queer joy on the page, despite Theo and Asher’s emotional hiccups. Discuss where you as a reader found these moments of queer joy, and why illustrating such moments is important.
6. From the title’s allusion to wings and the tagline’s reference to catching flights to Asher’s occupation as a pilot, the motif of flight makes a notable mark in this novel. Discuss how this motif shows up in Theo and Asher’s relationship as it starts to take form.
7. Family plays an important role in the book. Discuss to what extent family often factors into one’s decisions in love. Where is the line between support and influence?
8. Clint is a vibrant character, to say the least, and makes an appearance in some of the story’s most dramatic moments. To what extent do you believe Clint basks in the theatrics of a relationship? Can someone like Clint ever be ready for real, mature love? Discuss.
9. Throughout the course of the competition, Asher and Theo adopt the phrase “winging it with you.” Discuss what this means to you in the context of a relationship. In what ways did the title prime you for Asher and Theo’s love story?
10. What’s next for Asher and Theo?
