The girls try to cough up enough money to pay for a new roof. Meanwhile, Sophia learns that a famous artist is dying, so the girls head to an auction to bid on one of his paintings.
Sophia goes into action to break her friend, Lillian out of "the worst nursing home in the city." However, Lillian proves to be too much of a handful for Sophia.
Mother and daughter move Rory into her dormitory at Yale, where she meets a strange new roommate, Tanna, and learns that her old adversary, Paris, will also be sharing her room.
At her first Yale party, Rory encounters twins who were instructed by Emily to keep her safe. Meanwhile, Lorelai and Sookie cater a kids' "Lord of the Rings"-themed birthday party.
Rory goes on her first date since Jess and finds that college dating isn't going to be easy. Lorelai invites Luke over for the traditional movie night she used to share with Rory.
Biology teacher Claire is a bridesmaid and conducts a class on Blue Island. Claire takes action when she learns her former boyfriend works for the developer building a resort on Blue Island. Stars Leah Renee, Chris McNally.
A travel-averse journalist chases her dream assignment where she unwillingly finds herself mentoring a handsome B&B owner who wants to be a tour guide. Stars Jen Lilley, Chris McNally.
Maddie is doing everything she can to save her cupcake business. With the help of a handsome investment banker, Maddie's luck begins to turn around in all aspects of her life. But then her first love Nate unexpectedly returns.
Jennifer's real-estate agent pal dies while trying to negate rumors about a home she's selling. The police believe there was no foul play, but Jennifer suspects that her friend was killed after she researches other deaths.
Dorothy is in charge of a charity show and things are going wrong. When her emcee cancels, Rose convinces the girls to scour Miami in hopes of getting Bob Hope to emcee. Guest Stars Bob Hope
