On Valentine's Day in February 2014 Amy and Justin both unexpectedly ended up at the same bar in town. Amy with her best friend and Justin with some guys from the fire department made plans with a mutual friend to meet at Pies & Pints in Middlebury, Connecticut. Brief introductions, casual conversation, and a few drinks later Amy and Justin parted ways for the night. However, as fate would have it, they found themselves running next to each other at the gym the next day, and a spark was ignited.

On a cold Sunday in December 2017 Amy and Justin set off to find the perfect Christmas tree at a local tree farm. The plan was to meet Justin's sister and her boyfriend (at the time, now husband) at the top of the hill to look for the best tree to cut down. After arriving Amy and Justin set off to find Donna and Andrew in the farm, they spotted them in the distance and walked towards the clearing. Justin noted to Amy that there was a present with her name on it under the tree ahead. Amy, not knowing what to expect, went over picked up the bag and found a St. Louis Blues jersey inside. Still not knowing, Justin prompted Amy to turn the jersey over. There on the back was the name "Nelson" and when Amy looked up Justin was down on one knee.