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.
Lorelai is forced to miss the winter carnival when Richard's haughty mother insists on having dinner with Richard and Emily at the inn and makes a surprise announcement.
Rory's manipulative classmate Francie convinces Paris that Rory has been plotting against her. Meanwhile, Lorelai meets an interesting man, Alex Lesman, at a business seminar.
After agreeing to go on a fishing date with Alex, Lorelai asks Luke for a lesson on fishing techniques. Meanwhile, the political battle between Rory and Paris escalates.
When Christopher's pregnant girlfriend, Sherry (MÄDCHEN AMICK), begins labor and asks Rory to stay with her at the hospital, Lorelai reminisces about the day Rory was born.
Rose is crazy about her latest boyfriend, Ernie, but can't understand why he doesn't approach the subject of sex so when she forces the subject she learns the truth.
When Sophia sets Dorothy up on a blind date, Dorothy falls for the seemingly simple man. Meanwhile, Blanche and Rose join the "Be a Pal" program for motherless girls.
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
A widowed surgeon visits her family's pear orchard in hopes of reconnecting with her distant son. She starts to fall for the farm manager, Will, who is growing a new hybrid pear, and teaches her the importance of her heritage.
A down-on-her-luck young woman falls into a job as a personal assistant to a star quarterback. He's never had a female assistant before, and she knows nothing about football. Stars Emily Kinney, John Reardon, and Joe Theismann.
Lorelai goes away with her new boyfriend, Alex, for a weekend in New York, but she worries about leaving Rory and Jess together. Meanwhile, Rory accuses Jess of fighting with Dean.
Rory accompanies Lane to a hockey game, where she encounters Dean and his new girlfriend, Lindsay. Meanwhile, Lorelai confronts Jess about his poor treatment of Rory.
While waiting for their college acceptance letters, Rory and Paris compete to give a speech. Meanwhile, Lorelai wonders if ending her engagement to Max was the right decision.
When a fire at the inn forces Lorelai to lodge guests in her own house, she spends the night at Luke's place. Meanwhile, Rory tries to decide amongst Harvard, Yale and Princeton.
Three brothers get the surprise of their lives when they are forced to work together and care for a baby over the holidays. Starring Paul Campbell, Tyler Hynes, Andrew Walker, and Margaret Colin.
The Brenner brothers are back and putting on a holiday pageant for young Thomas while trying to cope with life's curveballs, including their mom's new boyfriend. Stars Paul Campbell, Tyler Hynes, Andrew Walker, Margaret Colin.
Rose is crazy about her latest boyfriend, Ernie, but can't understand why he doesn't approach the subject of sex so when she forces the subject she learns the truth.
When Sophia sets Dorothy up on a blind date, Dorothy falls for the seemingly simple man. Meanwhile, Blanche and Rose join the "Be a Pal" program for motherless girls.
