Mike was sitting with a friend at a music festival in Eastport as she scrolled through her news feed. She landed on a photo of Crissy, who caught Mike's eye. Mike asked a few questions, namely if he could have her number. Crissy agreed to her number passed on and she and Mike went out on a blind date. They had great conversation that night and decided to keep seeing each other.

Mike decided to propose around their 5 year anniversary. They were house hunting and he wanted to wait until they'd found the one to pop the question, but the right place wasn't there. He decided to include one of Crissy's loves: her students. He coordinated with her friends at school and arranged to turn an ordinary Wednesday into one to remember. Crissy was called from her classroom to retrieve a trouble maker from music class, and entered the classroom to find her students holding a sign reading "Will You Marry Me?". After getting over the initial confusion, Crissy realized Mike was also in the room and what was clearly a ruse of some sort was also a very real request! As Crissy and Mike began sharing news and celebrating with friends and family, Crissy learned that she was quite possibly the only person who didn't know this was coming. In his joy, Mike just couldn't keep the secret from all the friends they encountered in the weeks leading up to the proposal.