Lorelai has to re-negotiate her status as “cool mom” during this episode, as she wonders whether Rory having a boyfriend will make a difference to their relationship. After suffering jealousy of Dean, inviting Dean on a date with she and Rory, letting Dean and Rory spend time alone, and then coming down as the heavy parent on Dean, by the end of the episode Rory is her best friend again who tells her everything – including describing kissing with her boyfriend.
We may well be wondering if there’s anything at all that Rory can handle on her own without her mother’s help, as school, homework, and even dating require Lorelai’s presence.
The Annotated Gilmore Girls 