2x13 - A-Tisket, A-Tasket
The annual Stars Hollow Picnic Basket Auction runs into romantic complications when Jess (Milo Ventimiglia) outbids Dean (Jared Padalecki) to win a picnic lunch date with Rory (Alexis Bledel), leading to a fight between Rory and Dean and an even bigger fight between Rory and Lorelai (Lauren Graham) over whether Rory should be hanging out with Jess.