Sarcastic, intelligent, hard headed, troubled, witty, caring. Played by Milo Ventimiglia, Jess was in my opinion, the best love interest that Rory had. He was complex but also very simple in that he liked very few things: Rory, books, his uncle Luke (even when he pretended not to), and being independent.
Jess made a lot of mistakes as kids do, but he was basically punished for even the tiniest thing, by the people of Stars Hollow.
His first appearance on the show explained briefly that his dad had never been in his life & his mom was flighty & clueless. He was getting into some trouble- as kids who grow up in such situations do. His uncle Luke takes him in.
Immediately after meeting Jess Lorelai doesn’t like him. She finds him rude of course but instead of acknowledging the fact Jess had zero structure, no guidance & no one to talk to for the first 16 years of his life, she just acts like he was a criminal or something. She tells people she doesn’t like him so then her cult (sorry, townspeople of Stars Hollow) believe it too and no one even gives him a chance.
Jess picks up on this because he’s not an idiot. Since he’s not used to knowing how to deal with conflict (let alone anything else) he just became determined to ignore them & take care of himself.
When people approach him, knowing how they felt about him he gets stand-offish.
Meeting Rory he can see she was intelligent as well as beautiful & is impressed that she wasn’t a sheep like the rest of the town. So he really likes her, hoping to be with what he felt was the only tolerable person in town.
As we get to know him we realize that Jess took care of himself & gained his knowledge purely from books. He learned some life lessons from them but clearly it isn’t enough.
Luke guides him in the best way. He let Jess be himself, they argued, he gave him advice & Jess acted out out by it but he stayed. Season 3 we see he even joked around a few times with him. And when Jess was being a jerk, Luke called him on it & tried to put an end to it.
We find out that Jess was with Shane (and it’s implied about other girls) because that’s the only type of girl who will give him the time of day. But he starts to realize that Rory might like him...and when they do get together he’s actually happy.
It’s the first time we really see him happy.
Jess shows progress when he starts dating Rory. He grows. He makes an effort to be more respectful of other adults, particularly Lorelai. He also shows actual interest in her friends.
When Rory was dating Dean & they had that impromptu dinner - Jess, Paris & Rory- Jess genuinely seemed interested in being nice to Paris & even potentially being a friend to her to.
He also seemed on good terms with Lane though they didn’t hang out.
Jess gets a job at the diner to help Luke out. He didn’t have to. He could have ignored Luke if asked to help. But he didn’t. Then he got a job at Walmart. He liked being able to take care of himself & get a jump on his adult life.
When he arrogantly assumes he could just write a few tests to graduate- and realizes he flunked out - he’s devastated. He knows he could easily have passed if he had just gone to class & that he royally screwed up.
Knowing he would disappoint Luke upset him. Luke’s rule was he had to go to class or he’d be kicked out. As he’s from an unstable background he probably believes Luke would actually send him away. His uncle likely would send him to New York but show up hours later to drag him back....as Luke wouldn’t let Jess ruin his life. Jess probably assumed even Luke had his limits.
However, the biggest upset about not graduating high school was not being able to take Rory to prom. He knew she’d be devastated but he couldn’t deal with how she’d feel about the fact he didn’t graduate. Instead of trying to deal with it (as he’s still a troubled kid) he runs away.
Jess finds his father in California & despite the fact the man tells him repeatedly that he can’t stay with him, Jess pleads with him & ends up staying so he can get on his feet.
He really was looking to find out who he was & why he was screwed up...like he had to understand why his dad was screwed up first.
It does seem to help give him perspective & to not be so angry.
The tough love relationship with Luke though was the best thing for him & we can understand that by seeing him in later seasons. He’s mature, enlightened & has a good relationship with his uncle Luke.
Jess goes back to Stars Hollow briefly & thanks his uncle. Gives him his number (reaching out & showing he wants to be in his life). He apologizes & wants to pay him back for everything. It’s heartwarming to see.
As a boyfriend Jess was obviously flawed in a few ways, particularly how jealous he’d get. If Dean was around, Jess likes to point out he was more intelligent & that he was a better intellectual equal for Rory. They also got into some fights. He tries to walk away a couple times but not always.
The difference though between his & Dean’s jealousy is that Jess never got scary angry. He did slip a few times & we saw how stupid he was about fighting but he never intentionally scared or hurt Rory.
There was a scene where he was getting handsy at the party then got upset when Rory wouldn’t sleep with him...but he had stopped himself from hurting her. It was still messed up & one of his main reasons for leaving town. He was ashamed & wanted to make sure he didn’t hurt her ever.
I think his leaving was good though. He needed to leave. For himself & for Rory. It was needed so they could both grow.
Eventually he realizes his mistakes & his feelings for Rory but it doesn’t fix what was broken. That’s one of the reasons why I love their story. He still loves her even though he gets nothing out of it. It also feels more...real.
I also love how after he professes his love, he knows it was too late & they were broken. But he doesn’t revert back to who he was because he had changed. Later we see he became a writer/poet & is getting his life together.
Jess even went to Yale & asked her to runaway with him. He was being the romantic he always read about. Unfortunately it didn’t happen but the rejection helped fuel his creativity.
Rory clearly had feelings for him but she didn’t trust that he wasn’t going to do something like leaving. She tells him she loves Logan but it felt almost...premature at that point. He tries to talk sense into her because Logan was immature- even more that Jess was when he met her. Plus he didn’t like what he saw in how Rory was treated (she wasn’t put on a pedestal like everyone else in her life had done in the past).
Rory didn’t understand Logan wasn’t interested in a monogamous relationship like she was then was being petty & jealous. She used Jess to try to get back at Logan. Jess was smart enough to see through it. I felt really bad for him because she knew he loved her.
Jess was hated from the start by nearly everyone in the show. A jerk, hoodlum, criminal etc...labels people gave him but he ended up as the most well rounded, evolved character of the series.
I hated how Emily was angry because of the dinner with him & Rory. But that wasn’t his fault. He was on his best behaviour. Rory pushed, pushed, pushed about his black eye. She insisted on delaying dinner even further to confront him about it. He was tight lipped (due to embarrassment) & she didn’t believe him when he said it wasn’t a fight. They argue then he ends up leaving because she pushed him away...it wasn’t intentional but he felt attacked & very uncomfortable. I’m not sure anyone else would have stayed. Lorelai wouldn’t have. She’d been know to up & leave too.
However, in the Gilmore Girls universe, everyone on the planet thought bailing on someone was charming for Lorelai & unconscionable for Jess. A double standard that always annoyed me.
Year in the Life even got Jess right though. He was a nice addition & we got to see how far he came. He gave Rory really good advice but he also was shown as mature & a good person. Though I think a quick mention of all the books he’d written would have been good...and a little tidbit or two about what else was in his life. Did he travel? Have a career? A dog? Girlfriend? I wanted more.
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