Rory’s three boyfriends on Gilmore Girls have their differences, but they’re all pretty good at one thing: being the “nice guy.” Not a genuinely nice person, but one who exhibits toxic traits under the guise of niceness. Jess, Logan, and Dean all do this at various points in the series.
No matter which team viewers are on, they can agree that none of Rory’s suitors are perfect. They sometimes make her a better person, but they also bring her down with their attitudes. When was Jess genuinely a good person, and when was he nothing but a “nice guy?”
Nice Guy: Buying Rory’s Basket
When watching season two’s “A-Tisket, A-Tasket” episode, some fans might be inclined to think that Jess is only trying to flirt with Rory. It’s not that innocent, though. Jess will do anything to pull Rory away from Dean, even when she attempts to stay with her first boyfriend. By out-bidding Dean at the basket auction, Jess puts up a nice façade but asserts his disregard for others’ wishes (even if he knows Rory wants to be with him).
Good Person: Sneaking Off With Rory And Kissing Her
Fans have mixed feelings about Rory and Jess getting together, but no one can deny that their nighttime kiss is a great scene. They meet in the evening at Gypsy’s, where Jess is supposedly picking up a car part. The entire interaction shows Jess being the sweetest version of himself. When Rory abruptly stops kissing him and says she needs to leave, Jess even cares whether or not he did something wrong.
Nice Guy: His Fake Brown-Noser Act
There are many times when Jess is putting up a goody two-shoes front with Luke or other adults in his life, but what he is really doing is mocking them and undermining their authority.
A great example is when Jess first moves in with Luke. Luke is trying to make his place a comfortable home for Jess, and Jess just loves to make fun of his uncle’s efforts (in a faux “nice guy” sort of way). Another classic instance of this is Jess dressing just like Luke to work at the diner.
Good Person: Letting Dean Be The Hero
Jess’s personality is often measured by his reactions to Dean’s presence in Rory’s life. He sometimes chooses to let Dean be the hero (since that is one of Dean’s biggest desires and downfalls). When Rory is house-sitting and has a sprinkler mishap, Jess happens upon the scene and helps her right away. But after hearing that Rory paged Dean for help, Jess turns the sprinkler back on and leaves. He’s not being dramatic, but he is trying to do the right thing in the situation. It is one of Jess’s best gestures during Rory’s phase of tension between him and Dean.
Nice Guy: Teasing Dean
Jess might respect Rory’s wishes sometimes, but other times, he wants to be as slick and haughty with Dean as possible while still managing to pass himself off as a cool kid. Not everything is as obvious as Jess’s stunt at the infamous dance marathon, but he has a way of inciting Dean within mere moments. The “who, me?” attitude Jess maintains is his way of distancing himself from any damage he causes.
Good Person: Honest Job To Pay For A Car
Luke gets upset when Jess buys a car because he knows that Jess could never afford it on the money he earns from the diner and cleaning rain gutters. When Luke presses Jess, the kid slyly answers, “I go to a place that gives me money… for my services.” After the awkwardness of what Luke is trying to say, Jess finally explains that he has been working at Walmart twelve hours a week for a few months in order to pay for the car. Though Luke makes fun of Jess, Jess’s job operating the forklift shows that he cares about being a good person and making an honest living.
Nice Guy: Running Away From Stars Hollow After Saying “I Love You” To Rory
Jess almost achieves a “good person” moment in telling Rory that he loves her, but he sabotages it all by running away. Jess struggles with commitment issues, but that’s no excuse for his literal back-and-forth with Rory, leaving and coming back and even asking her to drop everything and run off with him.
Jess might be trying to be good, but his zig-zag pattern of absentee love is only something a “nice guy” would try to get away with.
Good Person: Offering To Pay Luke Back
Jess and Luke have their share of heart-to-heart moments where both of them are able to cut through the sarcasm and be real. One of the best examples is when a slightly older, wiser Jess expresses his appreciation for all that Luke has done for him over the years. Jess thanks Luke honestly and even tells Luke that he wants to pay him back for everything. It’s an incredibly heartfelt moment, even inspiring Luke to tell Jess that he’s always there.
Nice Guy: Puts Pressure On Rory
One incredibly common “nice guy” problem in relationships plays out with Jess and Rory. When the two are alone together at a party, Jess tries to pressure Rory into having sex with him. Even when she expressly says “no,” Jess does not want to listen to her. This is the worst thing he does to her in the course of the show, and it sadly maps out his dangerous way of life.
Good Person: New Beginnings As A Writer
The original show leaves Jess at Truncheon Books as an up-and-coming writer. His personal growth up to the sixth season is obvious, and he treats Rory with kindness and respect when she stops by to see him (even if her reasons for being there are a little misguided). It is rewarding for fans to watch Jess respond with grace and courtesy, and it never gets old to watch the best of his character.
