Jake and Kelsey met at Skidmore during leadership training in advance of the 2012-2013 school year. Throughout the week of training their paths kept crossing—during lectures, mutual friends' parties and finally during white water rafting when Kelsey plucked up the courage to ask Jake for his number by telling him they "should play Mario Kart sometime." Thankfully Jake chose to see that as cute rather than lame and they've been together ever since.

Jake and Kelsey took a ski trip to Killington at the end of December. Their trip didn't quite turn out the way they had hoped when the weather turned icy which cut their day of skiing a bit short. Kelsey was planning on a quiet night of leftovers at the hotel, but Jake had other plans. He talked Kelsey into going out into the storm (which at this point had changed from an ice storm to a blizzard) to pick up a bottle of wine to have with their leftovers. They had just started walking through the small patch of woods leading up to the shops nearby when Jake stopped her next to a park bench. Kelsey thought they were going back for something until she saw Jake get down on one knee, right there in the middle of a snowbank. Later, Jake explained that he had picked that spot so that in years to come they could visit the bench to remember the moment.