Brought together by their love of the mountains, Jen and Ryan both found themselves at Sunday River Mountain in Maine during the early ski season. After a long day on the slopes the two descended upon the Matterhorn Ski Bar with their separate groups of friends. After several drinks and conversation across the bar their South Shore roots sparked a connection. When the night was over they exchanged phone numbers and shortly after set up their first date back home.

After months of pandemic quarantine, Jen and Ryan set out for a weekend getaway to Martha's Vineyard. Jen was anticipating the proposal but when their plans to watch the sunset on the beach didn't pan out she started to wonder when it would happen. Luckily Ryan was audible ready and had spotted a private spot by the harbor beach. While watching the boats come and go at sunset Ryan got down on one knee and popped the question!