Fans have varying perspectives on the main guys of Gilmore Girls. One thing that can be relied on is that if someone is an avid Logan fan, the next person will have ten reasons Rory should go for Jess or Dean. However, something that is discussed a bit less about these starring lads is how they stand as characters independent from their romantic value to Rory.
Jess is a character who may have one of the most tumultuous and complex backgrounds, with an interesting story that offers just enough fleshing-out for viewers to feel close to him yet always be curious for more. There's a mysterious charm that particularly captures viewers--but what exactly is this charm made of, and how much of it is simply the false bait of cliché?
10 Cliché: Ditches Lorelai's Dinner
Jess does not start off on a good foot as far as predictable angsty-teen behavior goes.
When Lorelai is perfectly kind to him and invites him to dinner at her house as a way of welcoming him to town, he first tries to ditch via Rory's bedroom window, and then opts to take a beer from the fridge and stay out on the porch whilst everyone else joins together at the table. He has reason to be upset about the move, but his behavior is worthy of several eye-rolls.
9 Classic: Joins A Publishing House
It's nice to see Jess finally begin to come into his own when Rory attends the open house of his publishing company.
It's one thing to spend all of his time reading books and using his superior knowledge of literature to look intellectual and cool, but when Jess actually takes his interest seriously and channels it into a passionate, tangible thing in his life, his character really begins to fill out and it makes all his bookishness feel authentic rather than pretentious.
8 Cliché: Skips School
School isn't for everybody, that's for sure. But it also doesn't help Jess's character, who already walks around with a bad attitude smoking cigarettes and disrespecting his elders, to skip school on top of it all.
He fits the bill for the stereotypical high-school bad boy who sticks it to the man, just because he can.
7 Classic: Loves Reading
Jess's love of reading could be seen as cliché--paired with the cigarettes and the leather jackets, it certainly pegs him in an obvious James Dean, try-hard category.
However, Jess is genuinely a cast-out, neglected kid (until he meets Luke), and it's clear that books are perhaps one of the few things in his life that he can rely on and enjoy--making his love of them one of his steady strains of authenticity in the show.
6 Cliché: His Style
The cigarettes, jean jackets, messy hair, and glowering expression make Jess the obvious mystery man in town--rather ironically, seeing as this style is so often taken on as a sign of mystery and therefore makes someone much less mysterious in their intentions.
The look works for Jess, but it is a little cringe to see someone who thinks of themselves as a free thinker to so obviously follow a set mold that society had just waiting for him to walk into.
5 Classic: Loves David Bowie
The characters in the show are known for their diverse taste in music and keen knowledge of the classics, and Jess is no exception.
It's a relief when his music taste proves to support his persona of artsy intellectualism. Jess is genuine in his interests, as viewers can see in the scenes where he seeks out music with Rory or plays music in Luke's apartment. There's even one scene where he and his father catch themselves bobbing their heads to the same David Bowie song--at odds in their relationship, but able to agree on this one thing.
4 Cliché: Abandons Rory
It's disappointing to see Jess succumb to the typical trope of the boy with a chip on his shoulder who fears commitment too much to be honest with the girl he likes.
Jess is into Rory from the moment he meets her, and he encourages her to leave Dean by flirting with her and making his interest obvious. But when things get too real, Jess disappears without even a goodbye.
3 Classic: Encourages Rory To Return To College
Jess sometimes serves as Rory's reminder of who she was and all she wanted to be, and in this way he is both a good friend and a mature person. Jess can see the value in a good education, and he admires Rory's ambitions.
When she diverges from her path and becomes lost in life, his encouragement for her to return to school reveals that he has her best interest at heart, as well as a practical, worldly side to Jess that has developed throughout the show.
2 Cliché: Picks Fights With Dean
It's painful to watch Jess and Dean argue. They both are interested in Rory, causing some natural jealousy, but both take the situation further by making it a contest of who is more tough and masculine, as if it isn't about Rory at all but about which guy is "man enough" to win over the girl, whatever girl it may be.
Jess, who prides himself in being above mainstream behavior, should know better.
1 Classic: Thanks Luke
When Jess finally thanks Luke for all he has done for him, it's like a breath of fresh air for fans who have awaited the moment for all of the show. Even supporters of Jess admit that he is not appreciative enough of Luke, and his obnoxious behavior feeds teen stereotypes.
However, he sees the error of his ways, and his apology is the classiest thing he could have done.
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