Two Strangers
25-year-old Englishman Dougal Todd flies to Christmastime New York for the wedding of his millionaire father, Mark, to 30-year-old Melissa. The sister of the bride, cynical 27-year-old New York native Robin Delafosse (Rainey in the Broadway production), picks Dougal up from JFK Airport. Irritated by his enthusiasm for the city he sees in films, Robin puts her headphones on as Dougal serenades plans to tour his wildly inaccurate list of landmarks ("New York"). At his hotel, Dougal calls his single mother and reads his wedding invitation, thrilled to meet his father for the first time in his life ("Dad"). In the coffee shop where she works, Robin reflects on her sideline life's monotony and wonders what she is missing ("What'll It Be"). Melissa tasks her with collecting the expensive wedding cake from Flatbush, Brooklyn, and Dougal joins along. The two bond over Robin's Tinder frustrations with "absolutely horrifying men" and "Perfect Justin" ("On the App"), her memories of childhood in Flatbush ("This Is the Place"), and the barely concealed sexual themes of Christmas songs ("Under the Mistletoe"). At Melissa's doorstep, Robin accidentally drops and destroys one of the cake's four boxes. Dougal reassures her; when he asks her about happiness, Robin rejects the proverb to "Be Happy", with the numbness her years spent pursuing it left ("Be Happy"). Robin reveals that she hadn’t seen her grandma in years. Dougal suggests a movie-style spree through Manhattan to cheer up. Robin points out the city’s high cost of living, asks him to leave, and calls Melissa, with whom she has a distant relationship. Dougal eats the dropped box of cake, returns, and helps Robin respond to a sudden series of messages from Justin, eventuallysecuring her a date. She instead spends the night spreeing with Dougal, using Mark's American Express card to enjoy the luxuries of Midtown Manhattan ("American Express"). The next morning, Robin wakes up confused, embarrassed, and stressed, and Dougal "another day in dreamtown"—together in a Plaza Hotel bridal suite ("The Hangover Duet"). Robin tries to persuade Dougal that meeting his father can never live up to his expectations, pleading him to leave his idealised image of Mark untouched ("He Doesn't Exist"). She finally tells Dougal that Melissa sent his invitation to get back at Mark for cheating, and that Mark had always kept Dougal a secret. A letter from Mark reveals he has persuaded Melissa to let Robin attend the wedding and expresses astonishment at Robin's purchases with her "friend", whom he obliviously invites. Robin again urges Dougal not to attend the wedding and spend another day in the city together. Having travelled specifically to meet his father, Dougal reacts with angered denial and accuses Robin of being jealous. They argue ("What Did You Say?") until Dougal realises that Mark cheated on Melissa with Robin. Dougal storms off. Outside the wedding at Trinity Church, he leaves a voicemail for his mother, reflecting on the events, his happiness, and his family's happiness ("About to Go In"). Robin, meanwhile, reflects on the opportunities she has deliberately let slip away and the ways she has pushed people away. She resolves to change (“This Year”). Later, Robin eats alone at a Chinese restaurant, where Dougal joins her with a tier of wedding cake he has stolen after deciding not to attend the ceremony. The two roleplay a movie-style wedding on their own terms (“Dearly Beloved”). As Dougal prepares to leave for the airport, he and Robin stroll through the city, reflecting on how their time together has changed them and how glad they are to have met (“If I Believed”). Robin gifts Dougal a snow globe and resolves to visit her grandmother. Before they part ways, they read each other's fortune cookies: Dougal's reads, "You will go on a cruise", while Robin's reads, "This time next year you will be happy."