Our first date started on the patio of River Bar in Assembly Row, one of Kaila's favorite spots. Kaila quickly discovered how good a listener Ryan was. Ryan felt like he was talking to a long-time friend even on their first date. The date was going so well they had to continue it inside at Earl's to escape the cold. It didn't take long to know a second date was needed.
Ryan told Kaila that his friend was in from out of town and wanted to meet up for drinks in the Seaport. He then suggested that they get there early so they could walk around Fan Pier, which made Kaila very suspicious. When they arrived in the Seaport Ryan told Kaila that his friend was having "car troubles" and was going to be late. The entire walk along the waterfront Kaila kept waiting for Ryan to make his move. Just when Kaila was starting to lose hope, Ryan suggested they walk up the stairs to the Fan Pier roof deck.