Caitlin made the move from Illinois to Boston to start her journey as a Music Therapist, but quickly realized that she needed a job to afford the city life-style. Fortunately, her friend helped her land a job at Charley's on Newbury Street, where a bartender (Tyler) was designated to "train" her. Tyler spoke a little bit about the job, but the two of them spent most of the time flirting and getting to know each other. Just about 6 months later (on Caitlin's 21st Birthday), the two had their first kiss...

Tyler asked Caitlin to marry him on her favorite day of the year- apple picking day! The day started as it usually does with Caitlin getting a delicious latte from their favorite coffee shop in the Berkshires (Dottie's) and then they headed to Lakeview Orchards. The day was cloudy and grey but that didn't matter to them. They ate apple cider doughnuts, bought an apple pie, and finally, Tyler asked Caitlin to take a walk with him around the orchard. They walked to the very top of the mountain and when fog finally cleared, Tyler asked Caitlin to spend the rest of their lives together. Tyler was sneaky and let Caitlin plan the day, but he made it, by far, her favorite apple picking day yet!