Kyle and Jen had planned a weekend getaway in the Berkshires. Every year since they met, they've gone shopping at the Lee Outlets a few weeks before Christmas. That particular year, in 2016, Kyle and Jen decided to get some skiing in at Jiminy Peak, too. The two figured a little shopping and skiing weekend was the perfect way to relax before the craziness of Christmas came about. Kyle and Jen have had plenty of weekend getaways and fun trips together since they've started dating, so Jen thought there was nothing particularly special about this weekend. After a day of shopping, they were getting ready to go to dinner at a rustic restaurant in Lenox, MA. While Jen was in the shower, Kyle ran outside to retrieve the beautiful hand crafted diamond ring he had been working on for the past 6 months. Just as Jen had finished getting dressed and was exclaiming, "okay, I'm ready!" Kyle whisked her into his arms and told her how amazing the past 3 years have been. As Jen started realizing what was about to happen, she instantly starting crying! Kyle got down on one knee and asked Jen to be his wife. In shock, Jen didn't say anything for a minute. Finally, she exclaimed a confident "YES!," followed by "Oh my God, can I call my mom!?"