We first met at our college orientation for transfer students our Junior year. Since we had the same major, we were in many of the same classes. Jason and his twin brother Nick and I would work on our homework and study together. I was in a relationship at the time, so Jason and I just remained good friends throughout college.
Fast forward to August of 2018. I was living in Manchester, NH and was spending a summer vacation at my parents house in Saratoga Springs, NY (close to where Jason was living). We had kept in touch over the years since we graduated college, and Jason had reached out to wish me a happy birthday on my Facebook wall. His twin brother, Nick, sent me a text wishing me happy birthday, and said that we should all get together soon to catch up. We decided to get together to play 9 holes at the Par 29, which Nick backed out- leaving just Jay and I to play. We had a great time catching up, and decided to go out for drinks later that weekend. Again, we had a great time and decided to continue hanging out. Jason came to visit me in NH, we hiked Mt. Major with Charlie. When the weekend was coming to an end, we decided that we wanted to continue seeing each other and made arrangements for another weekend visit. We continued these weekend visits for another year, until Jason moved to NH to live with Charlie and I, and the rest is history!
Jason planned a surprise trip for what I thought was my birthday. In the car on the way, I still did not know where we were going. We played 20 questions to find out where we were going, and I figured out we were en route to Newport, RI in about 7 questions. We got to Newport and continued driving by the parking lots for the downtown area of Newport, and continued driving until we got to Ocean Drive. At that point, I figured we were going to Castle Hill Inn- one of our favorite places and where we spent my birthday the previous year. I was ecstatic! We had some time before our dinner reservation and we were going to sit in the Adirondack chairs and watch the boats sail by. Before we sat down, Jason wanted to walk down to the water, so of course, I followed. When he got to the water line, I went to turn around and walk back to the chairs. That is when he said, "Sydney". I turned around and he was on one knee. Of course, I said YES!