Back at the island cottage after dinner, Emma and Maddy settle onto the porch and talk about Emma's upcoming date with Justin. Emma is unusually excited, but that excitement is mixed with uncertainty because the relationship began as a temporary plan to break their shared dating curse. Emma admits she likes Justin, yet she assumes he may only want to get through their arranged dates so he can move on to the woman who is supposedly meant for him.

Emma's mood shifts when her mother, Amber, suddenly calls from an unknown number after being out of contact. Amber says she is in Boston, explains that her phone changed, and reveals that she found Emma's childhood stuffed unicorn, Stuffie, in old boxes. The call briefly comforts Emma because Stuffie matters deeply to her, but Amber remains erratic and evasive, especially when Emma mentions being in Minnesota, the state Amber came from and rarely discusses.

After the call, Maddy gives Emma a DNA test and urges her to use it. Emma resists because Amber has long insisted that Emma's biological father was a married man who did not want children, and Emma fears disrupting a family that may not want her. Maddy argues that Emma deserves the chance to know whether she has relatives, siblings, or important medical history, so Emma finally agrees. They complete the kit, set the account to stay private except for a brief look at any matches, and plan to mail the test in the morning.

Later that evening, Justin sends Emma a joking pre-date SurveyMonkey questionnaire about timing, activities, clothes, food, greeting, and transportation. The gesture makes Emma smile and increases her anticipation because it shows effort and humor. Emma answers by choosing lunch, a surprise activity, casual clothes, a hug, and having Justin pick her up. The next morning, Justin follows up with a playful floral Evite for a surprise date and asks Emma to wear long pants, while Maddy tells Emma to watch how Justin handles rejection or competition because that will reveal his character.

Before the date, the cottage creates a series of practical problems that make the summer feel less idyllic. Emma and Maddy discover the water is unpleasant, the electrical system is so fragile that the hair dryer and toaster cannot run together, and island life leaves them dependent on one old pontoon boat for all transportation. When Maddy tries to dock the boat in strong wind, they nearly back the motor into the dock, which rattles both women and makes Emma realize how risky and inconvenient their commute will be. Emma takes over, gets the boat safely alongside the dock, sends Maddy back alone, and walks toward the mansion still shaken, where she finally sees Justin waiting in the courtyard.