Ep 14. It Should've Been Lorelai

In the fourteenth episode of the second season of Gilmore Girls, titled "It Should've Been Lorelai," tension continues to rise between Rory and her grandparents over her decision to attend Yale instead of the family's alma mater, Harvard. Richard, Emily, and Rory attend a Yale vs. Harvard football game, where Richard unsuccessfully tries to convince Rory to transfer to Harvard. Meanwhile, Lorelai is struggling at the Independence Inn as she deals with a difficult guest, an inept employee, and an unexpected visit from her mother.

The episode starts with Lorelai waking up to a chaotic scene at the inn as a snooty and demanding guest is causing trouble. Lorelai tries to placate the guest, Mrs. Lott, but nothing seems to be going her way, including the arrival of her mother at the inn's front desk. Emily stops by unexpectedly to deliver Rory's mail, and Lorelai begrudgingly invites her inside. Emily is disappointed to learn that Rory is still set on attending Yale and not Harvard, and the two have a tense but civil conversation.

At the football game, Richard and Rory are dressed in blue and white, while Emily is clad in crimson. Richard tries to sway Rory toward transferring to Harvard, arguing that it's a better school and that the family has a long history there. However, Rory remains steadfast in her decision to stay at Yale, causing Richard to become frustrated. During the game, Emily runs into an old acquaintance from her days in the Newport social scene, causing her to revel in the nostalgia of her past.

Back at the inn, Lorelai is still dealing with Mrs. Lott, who is demanding and unappreciative. Lorelai seeks advice from Sookie and Michel, who offer some comedic relief as they try to help her out. Meanwhile, a new employee at the inn, Tobin, is not doing his job properly and Lorelai struggles to find a way to motivate him. Eventually, Lorelai must enlist the help of her mother to deal with both Mrs. Lott and Tobin. Despite their differences, Emily is able to charm the difficult guest and give Tobin the motivation he needs to improve his work ethic.

As the football game comes to a close, Richard is still frustrated with Rory's decision to attend Yale. However, he puts on a brave face and congratulates her on Yale's victory. Emily also comes by to congratulate Rory, showing some subtle support for her decision. Meanwhile, back at the inn, Lorelai is finally able to relax and enjoy a glass of wine with Sookie and Michel, relieved to have survived another difficult day.

Overall, "It Should've Been Lorelai" is a humorous but also emotionally charged episode that tackles the ongoing conflict between Rory and her grandparents over her future plans. The episode also showcases Lorelai's struggles as a manager at the Independence Inn, while highlighting the complicated relationship between her and her mother.