Blanche's brother Clayton, visits Miami with a surprise, he has found the right person to make a commitment to, but Blanche still can't get over Clayton's sexual orientation.
Dorothy has been sneaking around so that Sophia doesn't discover that she's been dating Stan. However, when Stan proposes, Dorothy must reveal the truth to Sophia.
Blanche needs someone to entertain her visiting Uncle Lucas. She persuades Dorothy into going out with him and the two later come up with a scheme to get revenge on Blanche.
As Dorothy's wedding day approaches, everyone is making preparations. In the end, Sophia and Rose decide to stay with Blanche and Dorothy says a tearful goodbye.
The search is on for the missing winning lottery ticket that would give the girls $10,000. The search leads the girls to a celebrity auction and finally to a homeless shelter.
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
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.
Knowing they need each other to further their careers, two co-hosts of a travel show set in Hawaii clash over their production ideas, but soon realize they balance each other, on and off the screen. Pascale Hutton, Kavan Smith.
Fellow cruise passengers, Sarah and Jack, play matchmaker with their music loving widowed parents, as they cruise down the Danube visiting European cities. Stars Nazneen Contractor, Wes Brown, Kathryn Drysdale, Catherine Disher.
Elise is trying to keep her family inn afloat when the CFO of a major hotel chain checks in as a guest. Is he there to enjoy the fall season or try to take over her beloved inn? Stars Erin Cahill, Wes Brown.
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.
