Toby Fleishman, a recently separated surgeon, embarks on a new chapter in his life as he joins the world of app-based dating and experiences greater success than before. When Rachel disappears after they divorced, leaving him with their children and no information about her whereabouts or plans to return, Toby must navigate balancing parenting responsibilities, friendships, an expected promotion at work, and Manhattan's diverse dating scene. In this challenging situation, Toby realizes that he will never truly understand what happened to his ex-wife until he has a deeper understanding of the marriage itself. Libby is Toby's long-time friend and the narrator who helps him through these difficult times.
Toby's online date takes priority over Rachel's inconsiderate early drop-off.