Taylor first grew suspicious in winter of 2019. The Oliffs had graciously offered for her to stay with them during one of her clerkships in North Jersey. After coming home early one day from the hospital, she was surprised to find that Zach was not home! On the phone, he said that he and his mom, Doreen, had gone to help Grandma Anne weed and mulch her garden. Shortly thereafter, it started to rain. The two amateur deceivers returned home well after sunset in dry clothes. Taylor would later discover they had gone ring shopping with mother-of-the-bride and co-conspirator, Nancy, in South Jersey. Weeks later, Zach invited Taylor to a brunch held by his residency in NYC to celebrate the end of his intern year. He provided very little information about the event but said to dressed nice. As the two drove into the city on April 14, 2019, Taylor grew increasingly anxious. Zach was known for his big gestures over the years. Once in college, Zach purchased a 6-foot inflatable birthday cake for her birthday. After realizing the pump was not included, he spent hours blowing up the cake himself until his face was pink and the room was spinning. He had joked many times about his eventual big proposal. Iterations included jumping from a plane, leaping through a ring of fire, and taming a pair of wild lions. By the time they parked, Taylor, who does not often like to be the center of attention, was shaking. The normally talkative couple walked quietly toward Carl Schurz Park, where Zach said they could get some fresh air before the event. Walking down a curved staircase, they were met by a guitarist playing one of the couple's favorite songs. A hidden photographer captured the beautiful moment when Zach proposed. It was private, it was simple, and it was perfect.