Marshall met Caitlin when she was completing her college internship at Devereux School where Marshall was working. Marshall always thought Caitlin was beautiful but never had enough courage to ask her out. One day while Caitlin and Marshall were working, Caitlin overheard Marshall's mom had been in a car accident. That night Caitlin felt so bad, she made Marshall brownies and put them in his desk with a note the next morning. Once Marshall got to work, he opened his desk draw and noticed the brownies and note. (For those who do not know, Marshall does not like chocolate which Caitlin did not find out until later in their relationship.) This kind gesture gave Marshall enough courage to ask out Caitlin. Caitlin and Marshall had their first date at Brew City in Worcester, MA and several more before they became "Facebook Offical" on January 1, 2012.

Caitlin's birthday was coming up and Marshall wanted to plan a trip. He decided Maine would be the best spot to propose.