Kyle and Becca met on her 30th birthday on the slopes at Breckenridge Ski Resort. Not only did Kyle meet Becca, but he met the entire Ryan family. Kyle, always a good sport, led the Ryans around Breck all day and earned himself an invite to dinner. He joined for dinner, learned how to play Monopoly Deal, and then - three months later - asked Becca out on a date.

Kyle lured Becca back to Breckenridge, under the guise of a Ski Squad reunion in August 2019. Becca, cluelessly searching the mountain for the friends they were allegedly meeting, suspected nothing. At the base of Peak 7 Kyle proposed to Becca right where they first met.