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During the original run of Gilmore Girls, Jess Mariano walks into the picture and upends everything. He wreaks havoc in the town, causes a car accident that leaves Rory Gilmore with a broken wrist, and causes a rift between Luke Danes and Lorelai Gilmore. Eventually, he breaks up Rory and Dean, all before walking out of Stars Hollow without ever telling his then-girlfriend. Overall, Jess seems like your average, immature trouble maker, but was he really? When all is said and done, Jess actually turns out just fine, and looking back, he may have been the most mature and realistic member of the town however brief his stay was.  

In A Year in the Life, he turns into the responsible one

By the time the revival roles around, Jess appears to have aged into the role of a caretaker and confidant, ready to give a pep talk to those around him. Screenrant points out that Jess is the one who helps Luke work through his issues with Lorelai, and he’s also the one who comes into town to rescue his mother and her goofy husband from joining a vegetable cult.

Milo Ventimiglia and Alexis Bledel during "Behind the Scenes of "Gilmore Girls"" at Leonard H. Goldenson Theatre i
Milo Ventimiglia and Alexis Bledel | Mathew Imaging/FilmMagic

He also manages to give Rory a pep talk while he’s in town, too. Even though Jess had neither a fancy education or a stable home life, he turns out pretty good. If you really look at the facts Jess had it in him all along, he was just too angsty to utilize his own power.

With a less-than-ideal upbringing, he manages to make it on his own

Jess takes off from Stars Hollow without a clue as to what he was doing or where he was going. He didn’t have a high school diploma, and clearly had no one to depend on. When he pops back up in Season 4, things don’t look like they are going exactly swimmingly, but he is taking care of himself.

Sure, he lived in a studio apartment filled with mattresses and worked as a messenger, but he was alive and figuring things out. Yes, he was still pretty angry, but it looked like he might make things happen, and he eventually does.

He talks Rory into going back to school

Jess could have written Rory off as another spoiled rich kid, but his maturity shines through again in Season 6. By that point, Jess, then 20, has published a book and is marketing it to independent bookshops in New England. Rory, with her costly prep school education, is holding down the couch at her grandparent’s house after dropping out of Yale.

A chance encounter between Jess and Logan Huntzberger leads to an argument between Rory and Logan. Jess is the one who talks Rory into going back to school, even if it was haphazardly. Fans never get to see Jess again during the original run of Gilmore Girls, but most have to wonder if maybe Jess could have helped guide Rory in the right direction post-Yale. Perhaps he will do just that in the second incarnation of Gilmore Girls: A Year in the Life. Netflix is currently in talks to craft a second season, so maybe fans will get to see Rory and Jess’s relationship further develop.