In August of 2012, at The Beech Tree in Hyannis, Greg got the (liquid) courage to go up and initiate a conversation with Jess, with the hope of not saying something stupid and to see where things would take him. Although the relationship didn’t start that day, phone numbers were exchanged and they would randomly catch up when they would bump into one another out in Boston on random weekends. It wasn’t until Jess sent a “Happy Birthday Stranger!” facebook message, which led to some classic sarcastic back and forth banter, that they finally had their official first date on October 24th 2015, at Tony C’s in Assembly Row (Classy... we know).

Greg and Jess were up at her family's condo on Newfound Lake for a long weekend in October. Greg was ready to go with the ring and a plan of proposing on the top of Mount Cardigan, Jessie’s favorite place to hike. Things didn't go quite as planned when Jess decided last minute that she wanted to try a new mountain to hike. As they drove up towards the White Mountains, they found that the entrance to the trail was a lot more difficult to find than they expected. After driving around aimlessly, for what felt like forever for Greg, they passed a beautiful waterfall called Silver Cascade. They decided to stop and check it out. As they were walking up toward the waterfall, Greg had to run back to the car after realizing he left the ring in his backpack. On the walk, he sneakily asked a lady to snag a picture of him proposing. As he walked up to Jess, who was standing by a rock right at the edge the waterfall, he got down on one knee. Jess, in complete shock, got down on her knees with Greg and said that magic 3 letter word that would mark their beginning of forever. "YES!”