Kyle went to Stars Hollow High School and was good friends with Dean. He also hosted the party in 3.19, behind his parents back. At this party, Dean and Jess get in a physical fight after Jess yells at Rory, causing her to cry. Dean and Jess cause a lot of damage to Kyle's house, including breaking a fence. The police break up the party. This party was the main reason Jess left town, causing Rory and him to break up. Kyle's parents found out about the party and Kyle entered the Navy (unclear if this was because of the party itself). Kyle was good friends with Dean, and was part of his bachelor party (when Dean drunkly confesses his love for Rory to Luke). Dean also moved in with Kyle after Lindsay and him separated. While Dean lives with Kyle, we found out Kyle was wounded in the Navy and now has a hook for one of his hands. He finds that the hook helps him to meet many women.