On February 8th, 2021, Ilana and Jake went on their first date. They sat outside Quality Eats on the Upper East Side in 20-degree weather and talked about The Bachelor, The Jonas Brothers, the vaccine, and how cold it was. A little over two years, six Jonas Brothers concerts, eight seasons of the Bachelor franchise, two vaccines, two boosters, two Jets seasons, and one Barkley later, Jake proposed on 3/6/23 in that same spot.