Courtney crashed his sister’s brunch with her college friend, Nikki, in New York City. After leaving brunch to go on a date, Courtney quickly realized his date was boring, and his sister's college friend, Nikki, is a vibe. He then ditched his date to meet up with his sister and her friend, and the rest is history.

While suffering from tonsilitis, Nikki was tricked into a two-day trip to Brooklyn, New York. The story goes like this: Courtney misled Nikki into believing he had a "work trip" in New York City and that going home and enjoying the city without family pressures would be fun. While Nikki relaxed and worked from the Moxy Hotel in Williamsburg, Brooklyn (fun fact: one of Nikki’s favorite hotel brands is the Moxy Hotel), Courtney, his two best friends, Aymeei and Alyceson, and Nikki's cousins (s/o to Chrissy, Court, Jilly, and Sam) all hustled to decorate the Moxy Rooftop. As the girls worked to get everything in place, Courtney took Nikki to Please Don't Tell, one of her favorite cocktail bars and speakeasies in the East Village. When they returned to the Moxy, staff from the hotel greeted the couple with masks and said their presence was requested on the rooftop. Once the elevator doors opened, Nikki stepped out to a private event, with rose petals guiding her steps. Once she realized what was happening, she looked up to see all of their close friends and family and burst into tears.