A double date between Lorelai and Luke with Rory and Dean goes wrong. Emily and Richard are getting use to living separately but accompanied by a panic room and a glittering vest.
Dean is still doing some work at the Dragonfly, but is avoiding Lorelai. In an attempt to show Rory that she's okay with her relationship with Dean Lorelai insists that they hang out together, like they use to. Rory thinks it’s going to be weird and Luke isn't happy with the idea after agreeing to a double date. Rory goes to Dean’s new place where he is Kyle's roommate. Dean’s not sure about the double date thing, either, but Rory talks him into it.
The date has an awkwardly polite start with Dean explaining to Luke how to do date night, which includes getting food from Al's Pancake World because the food is already bad to begin with, unlike the food from Luke's diner. The only movie Kirk has available at the theater is Pippi Longstockings. While Dean and Rory get popcorn, Luke complains to Lorelai about Dean and Lorelai insists that he gets on better terms with Dean.By the time they reach the Gilmore house Luke is still making Dean uncomfortable. Rory tries to remind them of the time they were on a softball team together, but that doesn't make anything better. Lorelai pulls out the Bop-It and the boys end up getting fiercely competitive. Luke wins and starts yelling about Dean being the loser. Dean leaves disgusted and Rory yells at Luke, letting him know that Bop-It is the Gilmores' solution to emergency social situations. After she leaves, Luke apologizes and tells Lorelai he doesn’t think Dean is good enough for Rory.
While at Friday night dinner, the girls learn that Emily has purchased a panic room. Emily takes the girls to the pool house ostensibly to get some gin, but really just to snoop since Richard is out of town. Emily finds plenty to shock her such as an abundance of breath mints and a glittering vest in the closet.
Elsewhere Zack hasn’t commented since Lane told him she likes him. Not knowing what she did wrong or what to do, Lane tells him she’s changed her mind and doesn’t like him anymore. Zach shows up at the diner later and says he’s a little slow and he was just processing. He likes her, too, but he’s going to need some time.
- Luke was a "pippi virgin".