Ashlee and Kyle first met through mutual friends at a Celtics game. Ashlee was at the game with her family and snuck away to "get some food" so she could meet him.

After finishing their junior years at Suffolk and Bryant respectively, Kyle asked Ashlee out on a date. Kyle picked her up in his "quiet" Mercury Sable and they headed out for an afternoon at Salisbury beach, a place Kyle learned was near and dear to Ashlee's heart. They hung out on the beach and tested their skills at the arcade. It still isn't clear if Kyle let Ashlee win or if Ashlee just dominated every game. Either way, Kyle learned how competitive Ashlee really is. They ended the night with dinner at Sylvan Street Grille but both were so nervous they ended up taking their food home!

Kyle proposed to Ashlee at Salisbury Beach where her family has a beach house. Over the years, and especially during the year they didn't have many places to go, the beach became just as much a part of his life as it was hers for the past 28 years. So, when Kyle was ready to pop the question it was a no brainer where he would do it. Where she spent all of her summers and their first date. Friday night of Labor Day weekend, Ashlee and Kyle went for a beach walk at sunset, as they did every night that summer, before they would “meet friends for dinner". After walking past all the houses on the beach, Kyle asked if Ashlee wanted to go up on the pergola to see views of the water. Thinking nothing of this, she agreed and walked up onto the sand: to a heart of rose petals and 4 tiki torches. Once Ashlee realized what was happening, she burst into tears as Kyle led her to the middle of the heart, gave his speech, and got down on one knee. When she said yes, her parents and friends popped up and came down to surprise her. They had been secretly watching the whole time! The light applause by the leftover beachgoers were a nice touch that Ashlee was convinced Kyle hired for dramatic effect. It couldn't have been anymore perfect. Let the celebrations begin!