Lorelai and Rory Gilmore's unique mother-daughter relationship evolves this season as Lorelai ponders a surprise marriage proposal and Rory enters her next year at the exclusive Chilton Academy and continues her on again/off again romance with Dean. Friday night dinners with Lorelai's uptight parents keep up the family tradition of fun and friction, and Lorelai continues to works at the Independence Inn while dreaming of opening her own B&B. Meanwhile, at Luke's, coffee's not the only thing brewing as the gruff proprietor (Scott Patterson, Saw IV, V) realizes that Lorelai may be more than just his best customer. The series also stars Melissa McCarthy (Samantha Who?) as Lorelai's best friend, Sookie St. James; Jared Padalecki (Supernatural) as Dean; Edward Hermann (The Lost Boys) as Richard Gilmore; and, new this season, Milo Ventimiglia (Heroes) as Jess, Luke's wild 17-year-old nephew. Plus, Chad Michael Murray (One Tree Hill) is a recurring guest star as Rory's classmate, Tristan.