#he just 1) didnt know stars hollow rory

[sunflowerinthekitchen]

To add on if I can: Logan doesn't recognize Rory is in a hole during that time because her condition is what HE wanted for himself. He was probably envious of Rory's "freedom" during her time off of Yale. She had endless funds (Emily and Richard supplying all of her basic needs and then some, including designer clothes, a whole pool house, food, and arguably spending money), she had no one forcing her to go to school or do things she didn't want to, and could party and hang out pretty well whenever.

Logan was very outspoken that if he could just not do anything and sail around on yachts, drink at pubs, and party with his friends, he'd be happy. If he could have his fully funded lifestyle without any of the catch (you must go to Yale, you just graduate, you must take your place in the Huntzberger business), it would be his dream come true. So when Rory has that opportunity fall into her lap, by leaving Yale and experiencing minimal pushback (she loses Lorelai but Emily and Richard are right there to support her and the decision and to Logan that didn’t seem like a big deal), why would he push her to go back? Why would he help her out of a hole he doesn't recognize? To him, school is a chore and an obligation. He doesn't understand seeing it as a dream to fulfill. He doesn't understand the gravity of Rory not speaking to Lorelai or cutting herself off from Stars Hollow. He doesn't understand how having no responsibilities can be a bad thing or a sign of trouble for Rory.

The entire time Rory is in this hole, she's itching for something to do. She polishes silver with the maid to talk to her and get to know her. Her community service grew to be something she loved doing because it gave her SOMETHING to do and she even became a leader in it. Getting a job was her idea from the beginning, the DAR was simply an in Emily could give her. She was excited about the job, and she also loved it because it gave her a purpose again. She poured her all into everything she did during the "time off" because Rory doesn't want time off. From childhood, she was involved in every Stars Hollow activity. She was on multiple committees and clubs in school, and she kept herself busy otherwise. But Logan doesn't know any of this about Rory and doesn't recognize in her that she wanted more, she was just lost and couldn't bring herself to go back.

Jess on the other hand, knows all of this and more about Rory. He knows how seriously she takes her schooling and how much time and effort she poured into getting into Harvard/Yale. He knows how much Lorelai means to her and what them not speaking truly means. He knows Rory's thoughts on so many things because they talked about everything! They were always discussing their views on something! They made fun of people like Logan together! Jess knows how devoted Rory was to her friends, her family, and her town. He saw all of it from the second he arrived in Stars Hollow until the moment he left. He's also smart enough to know that when those things are also that meaningful and important to someone, they don't change over the course of 2-3 years. Your fundamental views and opinions don't shift that drastically.

So yeah. Jess 100% understood Rory was in a hole and lost better than Logan ever could because Logan could never see it that way. He had no resources to be able to recognize how much she was truly drifting.

So I'm thinking right now of an issue that often came up on the Gilmore Girls subreddit, and that I often heard from L/L fans who intensely disliked Jess, which is that Jess was presumptuous to tell Rory in S6 that he "knew her better than anyone", that he only idealized the Rory he knew from high school, that he didn't know or understand her current circumstances at all, that he had no right to encourage her to go back to Yale, and that only Logan really understood the real Rory and knew what was best for her, because (and this is my absolute favorite part of the argument) "Rory likes having nice things and spending money."

I mean, objectively, some of these things are true, because she's spent the last year with Logan and Jess hasn't had much contact with her since high school. And yet...is she happy? Does she want to stay where she is? Is her relationship with Logan doing her much good? Is he doing much of anything to help her claw herself out of that hole? Is he encouraging her to go back to Yale? Is he giving her the push that she needs to fix her life?

And really...can Rory's personality be boiled down to someone who likes to spend money? Because in S6 as in the AYITL era, it seems more of a cushion that keeps her from moving on than anything that's really improving her life, and she only is able to move on when she embraces her roots and returns home to her mom, to Star Hollow, to furthering her goals, even if she doesn't play to stay home permanently.

ASP writes Logan as part of a toxic cycle, yearning for independence but unable to let go of the advantages he'll have to give up if he leaves. This seems to be a settled reality in AYITL: he can't leave, and she doesn't want to stay in his world, because she'd have to give up too much to live there. Her life is outside of there, and Jess is always an implied part of that future. Logan can't help her claw herself out of that hole because he can't find a way out of himself.

(Let it be known that S7 does not follow this blueprint and I think Logan can be better than that, but that wasn't in the original game plan).

And Jess? Well, he already did claw himself out of a life he didn't want. So he does know Rory better, and he is the right person to inspire her to change her life.

So don't be mad at my boy. He was right!