Drew and Maddy's first date was at Trillium Brewery by Fenway Park in Boston, MA in the middle of the pandemic. Restaurants only allowed outdoor seating, and their reservation got rained out. These two decided to give it a shot once the storm clouds cleared and the rest is history. They ended up chatting through the evening until Trillium kicked them out. They quickly scheduled follow up dates with pandemic rules -- lots of walks, wine picnics in the park, and game nights for two.

The scene was set: a fall weekend in New Hampshire. Maddy believed she had planned a festive fall weekend with Vicky, Drew's mom. A weekend coordinated by Maddy with both sets of parents in attendance was the perfect disguise for a proposal. Theresa, Maddy's mom, was on her best behavior, downplaying the the excitement of the weekend which had Maddy convinced nothing suspicious was going on. Drew had the day planned to perfection: the group would take a gondola to the top of Loon Mountain and Drew would propose with a stunning backdrop of fall foliage. The group, Maddy and her parents and Drew and his parents, all headed over to Loon to start their day. Drew was EXTREMELY anxious and wanted to get right to business, but Mother Nature had other plans... when the group arrived at Loon Mountain, they were told the gondolas were on wind hold. Drew was clueless on what to do next when his mom recommended they go for a hike and hope the wind calmed down later in the day. Drew made it clear that the parents were to ride in a car together while Drew and Maddy would ride together separately. It's not that Drew didn't trust the parents to act normal... okay, that was 100% why. En route to Sabbaday Falls, a favorite hike of the Crittendens, Drew was hard at work trying to come up with different proposal locations, including roadside pull offs with views of the mountains. When they arrived at Sabbaday, it was clear the nerves were hitting the parents as well: would the proposal happen here? Throughout the hike, all Drew could think about was identifying a location that might work out but nothing struck him as the right vibe for the big moment. After the hike, there was still no update on the wind hold. Unbeknownst to Maddy, who recommended the group go back for lunch and try the gondola later, they couldn't go back to the condo because family friends Karlyn & Jim were decorating. Drew decided they would pull off at one of the view points on the way back towards Loon. There was no cell phone service, so Drew had all but given up on checking for updates on the gondola. Upon arrival to the roadside viewing point, Drew began eying up where he might go down on one knee. The location would have the beautiful backdrop he was hoping for, but not the same vibe as the top of the mountain. But, as if a divine intervention, a single text message from Karlyn came through saying that the gondolas were off wind hold! The group immediately turned around to go back to Loon. The ENTIRE morning had disappeared, but things were possibly going to play out exactly as Drew had hoped. They arrived at Loon, took the gondola to the top and it was exactly as Drew had originally drawn it up: a beautiful backdrop of the mountains and foliage with both parents supporting them. Drew went down on one knee, and Maddy said yes (after which she promptly told Drew he better not drop the ring off the mountain). The group went back to celebrate with champagne, decorations, and of course Clemson football.