Kaylee was attending a ladies night out while Ryan was visiting his older brother in Rhode Island. This would be the very first time they would cross paths. Ryan and Kaylee had just left work and were both on their way to downtown Boston. They were in a hurry to catch the train at Back Bay Station. Once on the train, Ryan asked if he could sit next to Kaylee. After missing his stop intentionally so he could stay in touch with her, she left him with a bright smile. Little did they know the train ride from Boston to Rhode Island would be an everlasting ride together.