Gilmore Girls (2000)

S4E14 The Incredible Sinking Lorelais

In "The Incredible Sinking Lorelais," Rory finds herself struggling to keep up with her academic responsibilities. Seeking support, she turns to Dean, who is currently part of the construction team at the Dragonfly Inn. As they discuss her challenges, Rory opens up about her frustrations, highlighting the pressure she feels from her studies. This moment of vulnerability reveals the depth of their connection and sets the stage for further developments in their relationship against the backdrop of the inn's renovations.