Blanche's brother, Clayton comes to Miami for a visit and Blanche goes all out fixing him up on blind dates. However, Rose learns the truth, Clayton is gay.
Stan breaks the news that he's engaged to be married. However, after Sophia falls ill, Stan comforts Dorothy which sparks old feelings and she contemplates getting back together with Stan.
The death of a close friend, Esther Weinstock, brings Sophia face to face with Esther's husband a man whom she vowed never to speak to again. However, when Dorothy prompts them to make up they get a little too close.
Cheyenne and Van have a false pregnancy scare. Reba admonishes them for not taking more precaution and tells them they cannot have another baby while living there.
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.
Jess travels to Venice, California where his father, Jimmy, lives. The reunion causes tension with Jimmy's girlfriend. Also, Lorelai agonizes over paying for Rory's Yale education.
In the season finale, Rory and Lorelai happily prepare for Rory's graduation from Chilton. But major developments involving the Independence Inn threaten to dampen the festivities.
Upon returning from backpacking in Europe, Lorelai and Rory embark on a week of mother/daughter activities, in bittersweet anticipation of Rory going away to Yale as a freshman.
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.
Samantha returns home for her town's winter festival and her father's retirement from coaching. She is surprised to see that Jake, NFL quarterback and her high school sweetheart, is home as well. Stars Trevor Donovan, Lindy Booth.
A bookstore owner finds love and direction in life after agreeing to review a famous author's new novel in her blind-date-with-a-book club. Stars Erin Krakow, Robert Buckley.
Strangers Kelly and Parker both end up on the same Italian cruise, but after missing the boat during a stop, they're forced to team up and race across southern Italy to catch up. Stars Emilie Ullerup, Kristoffer Polaha.
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.
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.
