Kiss and Tell is one of the more poignant episodes in the first season of Gilmore Girls. It’s all about Rory’s first kiss with Dean and all of the complications that it causes. It shows the first signs of love between the two, but also relates it back to Lorelai’s situation and how fragile and even unfair that can be. Lorelai is afraid that Dean is like Rory’s father Christopher.
It turns out to be a sweet and innocent kiss right in the middle of the grocery store. However, Rory is so shaken up by the event that she mistakenly shoplifts. She also doesn’t know how to tell her mother Lorelai; even though they tell each other everything. Rory just doesn’t want Lorelai to freak out that she’s giving up on all of her hopes and dreams. This is something that happens often throughout the show. Sure, Rory is ambitious and really dreams of going to Harvard and works hard to achieve it.