Annie has always loved ice skating and suggested it early on for one their dates. Jason mentioned that he didn’t really know how to ice skate, but even Annie couldn’t have been prepared for the chaos that ensued. The ice skating rink was a very cute, albeit small, rink on an NYC rooftop next to the pier. Annie got on the ice first while Jason hobbled on after. Not 15 seconds later, there’s a thud and Jason is on the ground. This repeated several times over the next 30 minutes. One fall was particularly bad and got a collective “ooooo” from spectators. Unbeknownst to Jason, this was all extremely endearing to Annie and she asked to make things official later on at dinner that day.
On their trip to Alaska in December 2022, Annie and Jason scheduled some time to do a late night ice fishing + northern lights package. Apparently, all those hours of video game fishing paid off because Annie caught 4 fish throughout the night and took many Tinder fish pics. On the same night, they were also able to see the Northern lights, and their host took several photos of the two under the night sky. It was the most perfect and picturesque location for a winter proposal. But no, Jason did not propose then. He left the ring at the hotel because he was worried it was going to get lost during ice fishing. Instead, he proposed the next day in a snow-covered desolate forrest with no one around to take pictures, just a squirrel eating nuts. And she said Yes :D