Brittany and Matt met at Milestones Day School, a special education school in Waltham, Massachusetts, in September 2013. He started as a counselor/teacher’s aide in the high school while Brittany was working with the middle school students. They began building a friendship early on, eating lunch together and getting drinks after work with coworkers. Months later, sparks started to fly and a lifelong love started to bloom. They found themselves spending time together more often outside of work and spent many nights talking for so long they closed out the restaurant next to the school. Towards the end of the school year, Matt got a professional upgrade to English teacher and their relationship also got an official upgrade in May 2014. One morning before the students arrived at school, Matt asked Brittany if she would be his girlfriend and they've been together ever since.

Matt wanted to make Brittany his partner and soulmate for life and he knew it without a doubt in his mind. They had spent many getaways in the White Mountains and beautiful North Conway and Matt knew it was the perfect time of year for a romantic visit. They drove to New Hampshire over Brittany’s birthday weekend, when the leaves were at their most scenic and Brittany at her most bubbly. Matt nervously carried around the ring in his pocket as they hiked and enjoyed views of mountains, leaves, rivers, and covered bridges. Matt’s first attempt was nearly halted when he (in classic Matt fashion) rolled his ankle on one of the trails at the Basin. Matt did not let this stop him, instead taking Brittany to a new location the next day: the Flume Gorge. After traveling deep into the park, they came upon a wooden-bridge walkway over the river, passing directly beside Avalanche Falls. Brittany was more concerned with keeping her balance on the steep path but when Matt asked her to turn around, he was kneeling at the foot of the waterfall with ring in hand.