Dean is a cute, witty guy, who seems kind and down to earth. He doesn't come across as talkative, but a solemn type who gets on well. Dean plays softball, hockey and hangs out with guy friends, but no one he's specifically close to since the breakup.
Jess is incredibly smart, quick-witted, and interested in the arts and literature, but not academically motivated. His lack of parental support from his mother and the absence of his father leaves Jess feeling very alone and scared of the world, which causes him to test or lash out at most people.
Rory is an introverted, at times socially awkward person, who fares best in Stars Hollow, where she seems to feel comfortable being herself, as part of the town.
You're Jess Mariano's sister. You are a year younger than Jess. Your mother couldn't raise the two of you any longer, so she sent both of you to live with your uncle Luke in Stars Hollow.
You were the complete opposite of Jess. You didn't like trouble and avoided it at all costs. You were a rule follower. This caused Luke to compare you and Jess all the time. And, of course, this only pissed Jess off more. You two didn't get along. At all.
You figured out about Jess' little crush on Rory but didn't say anything about it. You never thought Jess would actually pursue her since she was dating Dean. You'd never met Dean, but you'd hear Jess complain about him.
You, to say the least, were wrong. Your brother pursued Rory anyway. Sure, he wasn't upfront about it, but he definitely did in subtle ways. Ultimately, this led to Dean and Rory breaking up. You couldn't help but feel guilty for your brother's actions. Even if you didn't know Dean, you felt horrible.
So, one autumn's day whilst walking down the streets of Stars Hollow, you spot Dean walking down the street. You gather the courage and catch up with him to talk with him...
Release Date 2026.07.08 / Last Updated 2026.07.08