Devin and Amanda first met while working at the Mystic Valley Regional Charter School, where Amanda was a Second Grade Teacher and Devin was a Physical Education Teacher. When they passed each other in the hallway, they would give each other a wave and say hello while nervous to express their feelings for each other.

It was not until the Christmas Party where Amanda's friend Kait, convinced Devin to talk to Amanda and buy her a drink to break the ice. The party continued at a local bar, Hugh O'Neills, where they talked and danced the night away. The night ended with Amanda and Devin exchanging phone numbers and Devin, who coached the middle school basketball team, said he would call her the next day after his first game of the season. As promised, he texted Amanda the next day and they quickly realized that they were two peas in a pod.

To celebrate their 5 year dating anniversary, Devin wanted to make sure this was a night Amanda would never forget. He planned to take her back to where they had their first date, ice skating at Frog Pond. Devin and Amanda had a "Christmas in Disney" vacation already planned, so while he was planning the proposal, she was off getting her hair and nails done for the trip. The timing could not have been any better for Devin to pop the question!

He planned for his father to drop them off in town, where he would hide behind a tree to take pictures of Devin getting down on one knee. While Amanda and Devin were lacing up their skates, an announcement was made for everyone to clear the ice as the zamboni was about to come on and clean it. At this point, he not only had to find a way to calm his nerves, but also make sure Amanda didn't catch on to his big plan. Finally, they were able to go back onto the ice where they skated around a couple of times, when Devin led Amanda to the middle of the rink. When they got to the middle, Devin started talking about their first date, got down on one knee where Amanda thought he was falling. He then said, "When you asked to go skating for our first date, I didn't want to tell you the last time I went skating was in elementary school. I said yes to impress you, and I want to impress you tonight and continue to impress you for the rest of our lives." The moment Amanda said yes, people started skating around them and clapping.

That wasn't the only surprise Devin had planned that night, he coordinated with Amanda's parents to meet up for dinner, where both of their families were waiting to celebrate! Needless to say, it was definitely a night they will never forget!