15 Times Gilmore Girls: A Year in the Life Gave Us All the Feels

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13.  Dean

The return of all Rory’s former boyfriends to A Year in the Life was eagerly anticipated as fans waited to see which one (if any of them) she was going to end up with. We see Logan almost right away and wait a little longer for Jess and finally near the end of “Fall” get a glimpse of Dean, Rory’s first and some would say best boyfriend. We last saw Dean in season 5 leaving Rory’s grandparents’ house after realizing he no longer fit into her life.

Rory runs into Dean at Doose’s Market (of course) and it’s all hugs and fond memories and catching up. Dean is married again, but now with three kids and another on the way (which is not too far off from Jared Padalecki’s real life). He looks good and he seems happy which is all anyone could want for Dean. Unfortunately out of all the candidates he seems most unlikely to get back with Rory again.

Rory tells Dean that she wouldn’t be the person she is today without him and that he, “taught her what safe feels like.” In her own rambling Rory way she is telling him that he was too good for her and she didn’t deserve him (at least the first time around). This reconciliation is one of the few moments we see Rory showing that in some ways she has grown up. It’s a small, but touching moment acknowledging the past these two characters had and what they meant to each other. (Although it’s a pretty crushing moment for those Team Dean holdouts.)