Ryan's older sister Emily was Siobhan's leader for a backpacking trip before freshman year of college. Ryan was the first boy Siobhan saw at Wheaton College, and because of his rugged handsomeness after nine days in the woods, she automatically fell head over heels for him. They spent hours together at camp, and shortly after they began their relationship. And now they're here!

Ryan flew out to surprise Siobhan in her hometown of Stonington, Connecticut. Siobhan's sister Haley and (then) boyfriend (now fiancé) Keith picked up Ryan. They all went to the farm that Siobhan worked at for two summers, Stone Acres Farm, where he bought a bouquet of one of Siobhan's favorite flowers. Ryan then went to the Jetty, a familiar point for the couple, and it was there Ryan surprised Siobhan. Together they walked down the Jetty, Ryan giving a speech telling her how much he loved her. At the point of the Jetty, Ryan stopped, got on one knee and asked Siobhan to marry him and spend the rest of their lives together. And she said YES!