Is She Really Going Out with Him?

The title of this novel is inspired by the song “Is She Really Going Out with Him?” by Joe Jackson. How does this song symbolically speak to Anna’s experience with dating? Without knowledge of the song, how did the title set your expectations of Anna and her view on love?

The story opens with Anna reading a fairytale to her son Ethan’s class. How does this scene illustrate Anna’s grapple with love and societal expectations?

As Lottie pushes Anna to get herself back out there—whether for dates or hobbies—Anna recalls the many divorced women she’s seen on Instagram who have “risen from the ashes,” and embraced their next chapter. Discuss whether this narrative around the post-breakup glow is one that is more helpful or harmful.

More in the pursuit of financial security than true love, Anna allows her children to pick her dates. How do you think her children’s criteria for choosing potential partners might differ from an adult’s?

Is She Really Going Out with Him? showcases how motherhood and professional and personal obligations compete with romance. How does Anna’s role as a mother—and wanting to protect her children—complicate her journey toward love?

Through Anna and Dan’s relationship, author Sophie Cousens paints divorce and singledom in an inspiring light. What do you think we’re supposed to learn from Dan’s character and Anna’s relationship with him?

Anna goes on numerous dates. To what extent do you believe dating is a numbers game? In the modern world, do you think it is possible to date entirely offline?

Anna and Will have a complicated dynamic. At what point could you discern Will’s more-than-friendly affection for Anna, even if she couldn’t? Which of his gestures gave him away?

Cousens is known for her well-drawn romance tropes, from friends-to-lovers to fated love. Discuss the tropes in this novel. Which trope would you want to experience if your life were a rom-com?