Gilmore Girls Season Two or Three?!!?

If you don't have season 1, then buy that first. Start buying the seasons in order. Season 3 has more of Jess and Rory being together, but overall season 2 has more of Jess. In season 2 is when Jess takes the bracelet Dean made Rory. Dean and Rory break up in season 2, he also gets married, and Lorelai breaks off her marriage to Max.