I know there has been a long time debate on who Rory ends up with after A Year In The Life, but I have a new theory after starting all the way back in the beginning.
In the beginning of Season 1: Episode 20 Rory and Lorelai are playing, " 1, 2, 3, He yours" at Luke's.
(BTW, Rory totally called it when saying that Luke was technically number 3.)
Anyways, when Rory's turn started, Dean walked by and was named #1 of the game. He was her first boyfriend. I think Jess was 2 and Logan was 3. It seemed like a way of saying she would have 3 important boyfriends in her life.
I think in a weird way, this might've been a way of telling us that she ends up with her #3, Logan. Towards the end of the limited series, she was together with Logan and it is definitely a possibility for her baby.
My main idea is that the game was a way to tell us that she would end up with the last guy. We didn't know who it was then, but after watching the show and A Year In The Life multiple times, some things start to line up. It seems like she ends up with guy #3 and and Lorelai did in a way too
