Caitlin and Kyle met at one of the notorious Munson bonfires. While they were slow to make things "official," Cait and Kyle knew they had a connection quickly. After weeks of Snapchatting, more bonfires, and fishing dates, they started dating on May 23, 2015. Caitlin and Kyle endured five years of long-distance while the two pursued their education. After graduating from their respective schools, Kyle joined Caitlin and Bailey (their Lab Mix) in Massachusetts and started their careers. They added Remy (their Golden Retriever) to their family during this time. After living in MA for a year, Caitlin was presented with a job opportunity that brought them back to New Milford, CT.

Block Island has always been a special place to Caitlin and Kyle. Since Kyle started joining Cait’s family on their trips, they would watch the sunset and take pictures at North Lighthouse. Kyle planned a weekend trip to BI and invited Cait's sisters. On July 23rd, the group spent the day going to their favorite spots and headed to North Light for sunset. Caitlin wanted to get pictures with Kyle but realized her sisters had walked down the beach. When Caitlin turned around, Kyle was on a knee. Many happy tears were shed. The rest of the night was spent celebrating.