Jess Mariano is one of the smartest characters on Gilmore Girls. He is well-read, perceptive, and subtly analytical. Due to all these qualities, some fans think that Jess is the perfect guy for Rory. He gives her and other characters in Stars Hollow all kinds of pointers throughout the series.
Jess's clever tips can be in earnest or just sarcastic, but he isn't afraid to speak up. He also, occasionally, speaks things into existence for other characters.
Worst: "Give It A Rest, Dr. Phil."
One of Jess's funniest moments on Gilmore Girls is when he tells Luke that he got "beaked" in the eye by a swan. Jess and Luke set sail to investigate, and Luke decides to fill Jess in on the extended world of Rory Gilmore.
Luke tries to explain to Jess that Rory's mom and grandparents are part of the deal when it comes to Rory. Jess doesn't want to hear it and advises Luke to drop the matter by saying, "Give it a rest, Dr. Phil." This sarcastic comment is not kind towards Luke, but it also is no good for Jess, who should care about what his girlfriend's family life is like.
Best: "Things You Lose Are Usually Right In Front Of Your Face."
The second season of Gilmore Girls includes the saga of Rory's special Dean bracelet. She drops it on the bridge while sharing her basket with Jess in "A-Tisket, A-Tasket." Jess pockets the bracelet at the end of the episode, but Rory doesn't even notice for a couple of weeks until Dean sees that the bracelet is missing.
Rory frantically searches for it, and Jess decides to return it quietly. He encourages Rory to keep looking and tells her, "Things you lose are usually right in front of your face." The advice is given deceitfully, but it's true in many circumstances. Lost objects are often right under a person's nose.
Worst: "Never Go Through A Lady’s Bag, At Least Not Until You’re A Couple Blocks Away."
Season two also brings the point where Jess's grades are slipping, along with his behavior in school. Luke is called in to discuss Jess, and the principal suggests a tutor. Before Jess and Rory hit the books after hours, Jess is seen slipping into class late and leaning over Lane's shoulder to ask her for a pencil.
During the exchange, Jess jokingly says that his mother always told him never to look through a lady's bag, "at least not until you’re a couple blocks away." Jess then says that he thought that was good advice. Even though the line is said in jest, it's terrible advice!
Best: Encouraging Rory To Take A Break And Eat
A classic Jess-centered episode of Gilmore Girls is season two's "There's the Rub." While Emily and Lorelai are away at a spa, Rory is planning on enjoying a quiet night at home and tells Dean that she can't hang out. But as fans know, Paris and Jess interrupt Rory's peaceful evening.
Jess pretends that Luke is sending Rory food, but he's really delivering it on his own behalf. Encouraging Rory to take a break and eat is really sweet, and it's generally good advice to stop and have dinner ... even though the whole night takes a bad turn when Dean arrives.
Worst: "I'm Never Going To College."
One of the worst pieces of advice Jess gives is to himself! There's nothing wrong with choosing a path other than college, but Jess exclaims that he isn't going to college and that Rory is the one going to college. Jess is not giving himself enough credit.
Rory is tutoring him in the episode "Teach Me Tonight." This is the one where Rory tells Jess to drive past the diner, Jess swerves to avoid hitting an animal, and Rory and her car are damaged in the accident. Before these pivotal events, Jess is opening up to Rory, but his declaration about his own future is discouraging.
Best: "Tell Me First."
Once Rory and Jess are finally dating in season three, Rory is still trying to be friends with Dean. She and Dean sit next to one another at one of Miss Patty's shows and end up in the press for their appearance.
Jess speaks with Rory on the phone about this news and asks her to tell him first next time so that he doesn't have to read about anything on a telephone pole. This is pretty good advice for a relationship so that everybody is on the same page and there are no surprises.
Worst: Encouraging Rory To Run Away With Him
Several episodes after leaving Rory with an "I love you," Jess returns to Stars Hollow for his mother's wedding. At the end of the season four episode "Last Week Fights, This Week Tights," Jess drives to Yale and finds Rory and Dean outside of Rory's dorm. Rory tells Dean to leave, and Jess says, "Come with me ... away. Don't think about it."
He doesn't know where he wants to go, but he suggests New York and a new start. Rory tells him that there is nothing to start. Jess says Rory can count on him and tells her, "You know we're supposed to be together." Rory refuses, so Jess walks out. Fans may never know what would happen if this scene had happened at a different time, but suggesting that Rory run away with him is not good advice.
Best: Telling Rory To Go Back To Yale
Speaking of college, Jess infamously returns in season six while Rory is taking her break from Yale. He goes out with Rory and Logan and can't stand Logan. Jess and Rory speak privately, and Jess tells her what he really thinks of her choices.
Jess calls Logan the kind of guy that Jess and Rory used to make fun of, and as for school, Jess asks Rory, "Why did you drop out of Yale?" Whether or not Jess has a right to judge Rory's life is another matter, but he does have a point. Jess knows how much Rory's education means to her, and he is pointing her back to her biggest goal in life.
Worst: "Focus On Your Own Life And Leave Everyone Else Alone."
Back in season four, Jess is stuck in Stars Hollow while Gypsy works on his dilapidated car. Luke is distressed over Liz's attachment to T.J. and tries to consult with Jess over how to get rid of T.J. Jess blows up at Luke and says that Luke is always interfering in other people's lives. Jess leaves his uncle with a stinging piece of advice: "Focus on your own life and leave everyone else alone."
Luke is hurt by those words, and some fans might agree with Jess. However, such advice isn't completely sound. The people in one's life sometimes need help, and it's okay to focus on the lives of others when it comes from a place of love, care, and respect for the other person's ability to make decisions.
Best: Suggesting That Rory Write A Book
Jess comes a long way from the series to the 2016 reboot. He and Rory have some wonderful scenes together in A Year in the Life, and Jess is ready to counsel Rory as she takes the next career steps.
He spends time with her in cozy settings, like the newsroom of The Stars Hollow Gazette, and Jess suggests that Rory write a book. The idea is perfect for Rory and brings her experiences from the series to her adult life full circle.