Jessie was working as an RN in the emergency department at Yale and Tyler had just started as a Branford Firefighter/Paramedic. Tyler transported a patient to the hospital and dropped him off as one of Jessie's patients, and the rest was history... JUST KIDDING. Jessie hit on Tyler and it took him 5 days to realize she was interested in him. THEN, the rest was history.

At Jessie's parents house in Skaneateles NY, Tyler told her that he wanted to take a nice picture on the dock before a date night. After taking a few photos with their pup, Tyler went to his camera bag and pulled out a ring, taking a photo as he proposed. Jessie almost fell backwards off the dock and Riley thought the ring was for her, and here we are!