Rory and Dean break up multiple times throughout the "Gilmore Girls" series. The first notable break up happens in Season 1 when Dean breaks up with Rory because she doesn't say "I love you" back. The more significant and public break up occurs in Season 3, Episode 7 ("They Shoot Gilmores, Don't They?"), when Dean breaks up with Rory during the Stars Hollow dance marathon. They briefly get back together later, even after Dean marries Lindsey, but ultimately, in Season 5, Episode 8 ("The Party's Over"), Dean and Rory break up for the last time after realizing they no longer work as a couple. Dean's last appearance is in that season, marking their final separation.
In summary:
- First break up: Season 1, Dean breaks up for lack of reciprocated "I love you."
- Major break up: Season 3, Episode 7, at the Stars Hollow dance marathon.
- Final break up: Season 5, Episode 8, after which they do not rekindle their romance.
Dean later appears in the revival "Gilmore Girls: A Year in the Life," where they meet briefly, confirming they have moved on from each other.
