LORELAI (to Emily): I can’t picture you at Teriyaki Joe’s . . . or in jogging shoes. What’s up, working girl?
A possible reference to the 1988 romantic comedy-drama film Working Girl, directed by Mike Nichols and starring Melanie Griffiths in the lead role. The film is about a secretary who aspires be a Wall Street executive, and steps into her female boss’ role after having her ideas stolen. The film received excellent reviews, and won the Academy Award for Best Song (Let the River Run, sung by Carly Simon).
Maybe Lorelai is referring to Emily (literally) stepping into Lorelai’s shoes in order to bond with Rory. As usual, Lorelai dislikes the idea of her parents getting close to Rory – it must have annoyed her that this outing was all Rory’s idea, with Rory inviting her grandmother to spend the afternoon in Stars Hollow with her.
The Annotated Gilmore Girls 