Season two of the Gilmores Girls is like a soap opera. The second season of The Gilmore Girls begins with Rory having feelings for Jess,Luke's nephew, while she's still in a relationship with Dean. Rory and Jess go for a ride in the car Rory purchased for her 6th birthday, the one Dean built for her. She allows Jess to drive, which results in an auto accident damaging the car pretty bad. Rory was placed in the uncomfortable position of having to explain to Dean what really happened and why Jess was in the car with her to begin with. All said and done, Dean and Rory were able to patch it up and continue their relationship. However, Dean secretly wonders if he has lost Rory's love to Luke's rebel nephew Jess.
Meanwhile Lorelai, Rory's mother, has been dating Rory's English teacher Max, even though she has feelings for Luke. Max eventually asks Lorelai to marry him. Lorelai breaks the news to Luke who takes it like a trooper as if he expected it all along and is very happy for her. Throughout the season Lorelai tries to warm up to the idea of marrying Max but never quite pulls it off. She ends it with Max, but not to fall into Luke's arms just yet.
Sookie's wedding to Jackson is one of the main highlights of season 2. Jess shows up back in Stars Hollow on the day of the wedding. He decides to attend the wedding and when Rory learns of his return, she runs right out to meet him, steals a kiss and runs back to the wedding where Dean is waiting. Christopher, Rory's father was also invited to Sookie and Jackson's wedding.With Lorelai on the rebound from Max she falls right back into old habits with Christopher. The night of the wedding they end up back together. For awhile during the season it appears they may be able to rekindle their lives together now as mature adults. Lorelai finds herself a few episodes later wondering if she may be pregnant with Christopher's child, again. The problem though is that Christopher is married. Unexpectedly, Christopher breaks the news to Lorelai that his wife is pregnant, unaware that Lorelai may also be pregnant. He tells her he has to return to his wife to do the right thing and try again. Fortunately for Lorelai she is not pregnant and she just has to sort out her emotions.
As the season comes to an end Rory and Lorelai make a nostalgic road trip to Harvard to see if this is where Rory wants to attend college. As always with Lorelai and Rory, the light banter keeps you smiling from beginning to end. Lorelai's father is a Harvard graduate and his wishes are for Rory to follow in his footsteps. Lorelai is constantly at odds with her parents, and would prefer it if Rory she doesn't choose to attend Harvard. Nevertheless, as much as she wants Rory to go somewhere else she wants it to be Rory's decision.
The season closes with Lorelai and Sookie looking for investors so that they can open the Inn of their dreams. Sookie is happily married. Luke is pining for Lorelai from afar. Dean and Rory realize that something has gone greatly wrong in their relationship. And Jess acknowledges he has feelings for Rory. We can hardly wait for season 3.