Twenty-five years after Jess Mariano first appeared on Gilmore Girls, Milo Ventimiglia is still hearing from people who remember the rebellious teenager he played back in 2001.
In a November 7, 2026, interview with Good Housekeeping, Ventimiglia reflected on the anniversary of his arrival in Stars Hollow and how much time has passed since then. He was only 24 when he started playing Jess, and he still finds it remarkable that audiences have remained so attached to the character.
I can understand why.
Jess wasn't exactly an easy young man to like when we first met him.
He was sarcastic, disrespectful, and seemed determined to antagonize anyone who tried to help him. He stole things, skipped school, challenged authority, and behaved as though everybody in Stars Hollow was beneath him.
If I'd been his teacher, I probably would have needed a vacation by Thanksgiving.
But Jess also had a sharp mind, loved books, and showed flashes of sensitivity that suggested there was more going on beneath that obnoxious exterior.
And as the series progressed, we discovered that there was.
Jess wasn't simply a teenager who enjoyed making adults miserable. He was a young man whose father had abandoned him, whose mother had struggled to raise him, and who had been sent to live with an uncle he barely knew.
That doesn't excuse his behavior.
I wouldn't have tolerated a teenager treating people the way Jess sometimes did, either.
But I also wouldn't have assumed that his behavior told me everything I needed to know about him.
And I think that's where Gilmore Girls gives us a worthwhile lesson.
A teenager can be difficult, disrespectful, and responsible for his own mistakes without being a lost cause.
Sometimes the hardest children to reach are the ones who most need an adult willing to look beyond their behavior.
And sometimes the adult has to be patient long enough for the child to become ready to listen.
Jess Arrived in Stars Hollow With an Attitude and a Suitcase
Jess Mariano made his first appearance in the second-season episode "Nick & Nora/Sid & Nancy," which aired October 30, 2001.
His mother Liz, Luke Danes's sister, was having trouble managing him in New York. So she arranged for him to live with Luke in Stars Hollow, Connecticut.
Luke, played by Scott Patterson, wasn't exactly prepared to become the guardian of a rebellious seventeen-year-old.
He ran a diner.
He liked his routines.
He didn't enjoy people interfering with his business.
And he wasn't a man known for lengthy discussions about feelings.
Frankly, putting Luke and Jess under the same roof was a wonderful recipe for disaster.
Luke wanted Jess to attend school, work at the diner, and behave himself.
Jess had other ideas.
Almost immediately, he began testing his uncle's patience.
He stole money from a donation container, took a garden gnome, and generally behaved as though the town's rules were an invitation to entertain himself.
When Lorelai Gilmore tried talking to him about how fortunate he was to have Luke helping him, Jess responded rudely.
Now, I wouldn't defend that.
Lorelai could be opinionated, and she sometimes assumed she understood a situation before hearing the whole story. But Jess had no right to treat her badly simply because he didn't want advice.
He was old enough to know better.
And Luke was right to insist on basic respect.
Still, I can imagine how Jess felt arriving in a strange town where everyone seemed to know everyone else's business.
His mother had sent him away.
His father had been absent for most of his life.
And now he was supposed to be grateful to an uncle who hadn't planned on raising him.
Perhaps gratitude wasn't the first emotion he was capable of expressing.
What I find interesting is that Jess seemed determined to reject Stars Hollow before its residents had much opportunity to reject him.
He acted as though he didn't need anybody.
He mocked the town.
And he made sure people had plenty of reasons to dislike him.
Then, once they disliked him, he could point to their reaction as proof that they weren't worth his time.
That's a pretty effective way to avoid getting close to people.
It's also a miserable way to live.
I wouldn't presume to diagnose Jess or assign a psychological explanation to every decision he made. He's a fictional teenager, not a patient being evaluated in a clinic.
But I do think the show gives us enough of his family history to understand why trusting adults might have been difficult for him.
And that's something I'd want a parent or teacher to consider before deciding the boy was hopeless.
Luke Didn't Know How to Raise Jess, but He Was Willing to Try
I think Luke deserves considerable credit for taking Jess in.
He didn't have to.
Jess wasn't his son.
Luke had his own life, his own business, and enough trouble dealing with the residents of Stars Hollow without adding a teenager who treated every rule like a personal insult.
But he opened his home anyway.
He gave Jess a place to sleep, a job, and expectations.
And he kept trying to reach him even when the boy seemed determined to make that impossible.
I admire that.
But I wouldn't pretend Luke handled everything perfectly.
He could be impatient and short-tempered. He argued with Jess, lost his composure, and at one point even pushed him into a lake after becoming fed up with his behavior.
The scene is played for laughs, and I understand why audiences found it funny.
But I wouldn't recommend throwing a teenager into a lake as a parenting technique.
Luke wasn't a trained counselor.
He was an uncle trying to figure out what to do with a boy who had already learned how to make adults regret taking an interest in him.
And occasionally Luke made mistakes of his own.
What sets him apart, though, is that he didn't regard Jess as disposable.
He expected the boy to attend school.
He gave him work.
He tried to teach him responsibility.
And when Jess behaved badly, Luke generally confronted him rather than pretending it was harmless.
I think that's important.
Compassion doesn't mean allowing a teenager to steal, lie, or disrespect everyone around him.
If anything, a child who has experienced instability may need adults who are consistent about expectations.
Not because strict rules magically solve emotional problems.
But because a young person needs to know where the boundaries are.
Luke was trying to provide something Jess hadn't always experienced: an adult who cared enough to remain involved in his life.
He wasn't always gentle about it.
He wasn't always successful.
But he tried.
And even after their living arrangement ended badly, he didn't stop caring about his nephew.
The Adults Saw a Troublemaker. Rory Saw a Boy Who Loved Books.
One of the reasons Rory Gilmore became interested in Jess was that she noticed an entirely different side of him.
Rory, played by Alexis Bledel, loved reading.
She was intellectually curious and enjoyed talking about books with people who could keep up with her.
Jess could.
He wasn't a poor student because he lacked intelligence.
He read constantly.
He had strong opinions about literature.
And he could discuss books in a way that caught Rory's attention.
Now, I'm not going to suggest that loving books automatically makes someone a good person.
I've known enough about human behavior to recognize that an intelligent person can still behave terribly.
And Jess certainly demonstrated that.
But his love of reading showed that he had interests and abilities many adults weren't seeing when they looked at him.
They saw the missing garden gnome.
The sarcastic remarks.
The boy who skipped school.
Rory saw someone who could discuss literature with her for hours.
Neither picture was entirely wrong.
And I think that's the problem with reducing a teenager to a label.
A child can be a troublemaker and still have talents worth developing.
A child can be academically capable and still make disastrous decisions.
And a child can behave as though he doesn't care about school while caring deeply about learning things that interest him.
Jess was proof of that.
He loved reading but didn't want to follow the school's rules.
Eventually, he worked so many hours at Walmart while skipping classes that he failed to meet the attendance requirements for graduation.
He couldn't graduate with his class.
He couldn't take Rory to the prom.
And he hadn't been honest with her about what was happening.
I don't think his love of books excuses any of that.
He made choices that cost him opportunities.
And he hurt Rory by keeping her in the dark.
But I also wish someone had been able to help him connect his intelligence and interests to a realistic plan for his future.
A teenager who spends his spare time reading doesn't necessarily hate learning.
Perhaps he hates the environment in which he's expected to learn.
Perhaps he resents being told what to do.
Or perhaps he's made so many poor decisions that admitting he's in trouble feels more humiliating than pretending he doesn't care.
In Jess's case, his truancy and refusal to follow school requirements were real problems. The show doesn't establish that he had a learning disability.
But I do think adults should be curious about the reasons behind a young person's behavior rather than assuming the behavior explains itself.
I explored a related problem in my article about Alfonso's dyslexia on Silver Spoons. Alfonso was struggling because of an unidentified learning disability, while Jess was making decisions that interfered with his education. Those aren't the same circumstances, but both stories remind us that adults need to understand what's happening before deciding they know everything about a child.
With Jess, the challenge wasn't discovering whether he was intelligent.
It was helping him recognize that intelligence alone wouldn't build the life he wanted.
And that was something he eventually had to learn for himself.
Understanding Jess Doesn't Mean Excusing How He Treated Rory
I want to be careful here because Jess has plenty of devoted fans.
And I know the debate over whether Rory should have ended up with Dean, Jess, or Logan can become rather intense.
But I'm not writing a campaign advertisement for Team Jess.
Jess treated Rory badly at times.
He was unreliable.
He kept important information from her.
He became jealous.
And when he was upset, he sometimes took his frustration out on her instead of explaining what was wrong.
The incident at the party in "Keg! Max!" is especially troubling.
Jess has learned that he won't graduate from high school.
He's angry and embarrassed, but he hasn't told Rory.
When she finds him alone in an upstairs bedroom, they begin kissing.
Then he tries to move the encounter further than Rory wants.
She tells him to wait, and he doesn't immediately respect her request.
When she stops him, he responds angrily, and she leaves the room crying.
I don't excuse that.
Rory had every right to stop the encounter, regardless of how upset Jess was about school.
His disappointment didn't entitle him to ignore her boundaries or make her feel responsible for his frustration.
And a difficult childhood doesn't change that.
We can recognize why someone struggles with relationships without excusing the harm he causes in those relationships.
That's the difference between compassion and making excuses.
Jess was young.
He had experienced instability.
And he clearly had trouble discussing his feelings.
But Rory wasn't responsible for fixing him.
She didn't owe him unlimited patience.
She didn't have to remain his girlfriend until he became a better person.
And when he eventually left town without properly explaining himself, she had every reason to be hurt.
I think the show was right to let their relationship fall apart.
Sometimes two people care about one another but aren't ready to build a healthy relationship.
And sometimes the person who needs to grow has to do that work without expecting a romantic partner to stand by indefinitely.
Jess eventually became more mature.
But that didn't obligate Rory to reward him with another relationship.
His personal growth had value whether or not they ended up together.
Luke Had to Set Limits, Even Though He Loved Jess
By the end of the third season, Jess had stopped attending school regularly and was told he wouldn't graduate.
Luke had made an agreement with him about finishing school.
When Jess refused to repeat the year, Luke insisted that he couldn't continue living under the same arrangement while ignoring those expectations.
Their relationship reached a breaking point.
Jess left Stars Hollow and went to California in search of his estranged father, Jimmy.
I don't think that was a happy ending.
Luke had tried to help, but Jess wasn't willing to accept the conditions that came with living in his home.
And Jess wasn't ready to acknowledge how much he needed guidance.
This is where parenting, especially parenting a teenager with serious behavioral problems, becomes difficult.
How long do you keep making exceptions?
What do you do when a child refuses reasonable expectations?
How do you establish consequences without making the child feel abandoned all over again?
I don't pretend there's an easy answer.
Luke wasn't dealing with a little boy who had forgotten to do his homework.
He was dealing with an older teenager who was refusing to attend school and rejecting the arrangements Luke had made to support him.
Luke had the right to establish boundaries.
But Jess also needed to know that a failed living arrangement didn't mean his uncle had stopped loving him.
And I think their later relationship helps answer that question.
Luke remained part of Jess's life.
The two men gradually developed a relationship that was less about Luke trying to control every decision and more about mutual respect.
Jess began taking responsibility for his choices.
And eventually, he was able to acknowledge something that would have been almost impossible for the teenager who first arrived in Stars Hollow.
He appreciated what Luke had done for him.
The Most Meaningful Change Was Jess Thanking Luke
One of my favorite developments in Jess's story comes in the fourth-season episode "Last Week Fights, This Week Tights."
Jess returns to Stars Hollow for his mother's wedding.
He and Luke have had a complicated relationship, but they're beginning to communicate more openly.
And Jess tells Luke that he wants to repay the money his uncle spent supporting him.
Then he expresses appreciation for everything Luke did.
Not merely the money.
The place to live.
The effort.
The fact that Luke was there when Jess needed someone.
I think that scene says more about Jess's growth than any romantic declaration he made to Rory.
Because the teenager who once mocked nearly everything his uncle said is now capable of acknowledging another person's sacrifice.
He recognizes that Luke was trying to help.
And he wants his uncle to know that the effort wasn't meaningless.
Luke responds by making it clear that he'll continue being there for Jess.
I love that exchange.
There's no grand speech about how Jess has become a perfect young man.
Luke doesn't pretend the previous years were easy.
And Jess doesn't suddenly become sentimental about every childhood experience.
They're still Luke and Jess.
A couple of stubborn men who aren't especially comfortable discussing their feelings.
But now they're trying.
And I think that effort is worth recognizing.
A young person doesn't have to repair every mistake overnight to demonstrate growth.
Sometimes progress begins with an apology.
Or gratitude.
Or finally recognizing that the adult who kept setting rules wasn't necessarily trying to make life miserable.
Luke couldn't force Jess to appreciate him when he was seventeen.
But the fact that Jess couldn't appreciate him then didn't mean he never would.
That's what I find encouraging about their story.
An adult's guidance may not seem successful at the moment it's given. Sometimes its influence becomes visible years later.
Of course, that isn't guaranteed.
Not every troubled teenager eventually returns to thank the person who helped.
But Jess gives us an example of what can happen when a young person grows mature enough to reconsider the people and experiences he once rejected.
Jess Wrote a Book. And He Did It Without Becoming Someone Else.
By the sixth season, Jess has moved to Philadelphia and become involved with a small publishing company, Truncheon Books.
He's also written a short novel called The Subsect.
When he visits Rory to show her the book, she's astonished.
The boy who skipped school and couldn't graduate with his class has become a published author.
I think that's wonderful.
Not because publishing a book suddenly makes Jess morally superior to anyone else.
And not because everyone who struggles in school needs to accomplish something extraordinary to prove the adults wrong.
What makes it satisfying is that Jess has found a way to use an ability he possessed all along.
He loved books when he was seventeen.
He loved reading when everyone else was complaining about his attitude.
And now he's doing meaningful work in a field connected to that interest.
He didn't have to become a doctor.
He didn't have to attend an Ivy League university.
He didn't have to follow the same path Rory was taking.
He found his own direction.
And he did something with it.
I wouldn't use Jess's experience as an argument that education is unnecessary.
His decision to abandon high school caused real problems, and he might have benefited from completing his education.
But the fact that he made poor choices at seventeen didn't mean the rest of his life had to be defined by them.
And I think that's the important distinction.
A teenager's failures deserve attention and consequences, but they shouldn't become a permanent prediction of who that teenager will be.
Jess had to change his habits.
He had to learn how to work with other people.
And he had to develop enough discipline to write a book and contribute to a publishing business.
Those accomplishments required effort.
The same boy who couldn't be bothered to attend school consistently eventually found something worth applying himself to.
I wouldn't call that a miracle.
I'd call it growing up.
And I think many parents would be relieved to see that kind of change in a child who'd spent years testing their patience.
Jess Became the Person Who Challenged Rory
When Jess visits Rory in the sixth-season episode "Let Me Hear Your Balalaikas Ringing Out," their situations have changed dramatically.
Jess has written a book.
He's working in publishing.
And he seems to have found some stability.
Rory, meanwhile, has dropped out of Yale after a painful setback involving newspaper executive Mitchum Huntzberger's criticism of her abilities.
She's living with her grandparents.
She's become involved with the Daughters of the American Revolution.
And she's drifting away from the educational and professional ambitions that once defined her.
Jess is stunned.
He remembers the girl who loved school and worked constantly toward her goals.
And he wants to know why she's abandoned them.
His confrontation with Rory has become one of the show's most frequently discussed moments.
He questions her decision to leave Yale and challenges the direction her life has taken.
Now, I wouldn't argue that Jess single-handedly saved Rory's future.
She already had complicated feelings about leaving school.
She had to make her own decision about returning.
And the conflict with her mother was hers to resolve.
But Jess helped her confront questions she'd been avoiding.
And I find that reversal fascinating.
When they first met, Rory was the academically focused girl trying to encourage Jess to make something of his abilities.
Years later, Jess was the one reminding Rory that she was capable of more than the life she'd settled into.
He could challenge her because he knew what her ambitions had meant to her.
And because he'd experienced his own period of making poor decisions.
I don't think that made him an authority over Rory's life.
But he had earned the right to speak from experience about changing direction.
He'd done it.
And he knew she could, too.
That's a wonderful example of how personal growth can change the role someone plays in other people's lives.
Jess was no longer simply the troubled boy Rory wanted to understand.
He had become a man with something useful to offer.
Jewish Wisdom Doesn't Ask Us to Pretend People Never Do Wrong
There's a teaching in Pirkei Avot 2:4 that encourages us not to judge another person until we've stood in that person's place.
I think it's an excellent lesson for the residents of Stars Hollow.
Jess was rude.
He was dishonest at times.
And he made decisions that deserved criticism.
But how many of the adults who dismissed him had experienced what he had?
How many had grown up with an absent father and a mother who couldn't provide the stability they needed?
How many had been sent away to live with a relative and expected to feel grateful immediately?
I wouldn't suggest that understanding those circumstances meant ignoring his misconduct.
Jewish moral teaching doesn't require us to pretend that harmful behavior is acceptable.
But it does ask us to recognize that our knowledge of another person's circumstances may be incomplete.
And that can affect how we respond.
A parent or teacher can say, "What you did was wrong," without saying, "You are a worthless person."
Those statements are very different.
One addresses conduct.
The other condemns the individual.
Jess needed adults who could make that distinction.
Luke certainly became frustrated with him, but he didn't regard him as a human being beyond hope.
And Rory saw abilities that other people weren't paying attention to.
Neither person was capable of solving every problem in Jess's life.
Nor should they have been expected to.
But their willingness to see more than his worst behavior gave Jess relationships he could eventually appreciate.
There's another Jewish concept I think belongs in this conversation: teshuvah, often translated as repentance or return.
At its heart is the possibility that people can recognize wrongdoing, change their behavior, and move in a better direction.
I wouldn't claim Jess's story follows every step of religious repentance.
He doesn't deliver a formal confession covering every mistake he made.
But he demonstrates important parts of personal change.
He begins taking responsibility for his future.
He develops a more respectful relationship with Luke.
And he uses his abilities to build a life that doesn't revolve around antagonizing the people around him.
That's the kind of progress I'd want to encourage in a struggling teenager.
Not a promise that the past never happened.
But proof that the past doesn't have to determine every decision that follows.
Giving a Teenager Another Chance Doesn't Mean Giving Him Unlimited Chances to Hurt People
I think it's important to make one final distinction.
When I say Jess deserved another chance, I don't mean everyone he hurt was obligated to forgive him or resume the same relationship.
Rory didn't owe him another romance.
Lorelai didn't have to trust him immediately.
And Luke didn't have to abandon every rule simply because Jess had experienced a difficult childhood.
A second chance should involve an opportunity to make better choices.
It shouldn't require other people to tolerate the same harmful behavior indefinitely.
That's why Jess's adult accomplishments are so much more convincing than an apology would have been on its own.
He didn't merely tell people he had changed.
He began living differently.
He wrote a book.
He worked.
He built relationships around something constructive.
And he acknowledged his uncle's help.
I wouldn't claim that made him perfect.
Adults can still make mistakes, and Jess undoubtedly had more growing to do.
But he'd moved well beyond the teenager who seemed determined to destroy every opportunity placed in front of him.
What I'd want parents to take from this story is a willingness to look for signs of progress rather than constantly reminding a child of past failures.
If a teenager begins taking school seriously after years of neglecting it, encourage the change.
If he starts respecting boundaries, recognize the improvement.
If he begins accepting responsibility, don't insist that every previous mistake proves he's still the same person.
And if a young person has already hurt others, help him understand that rebuilding trust takes time.
People don't have to forget what happened.
But they should be allowed to recognize when someone has genuinely changed.
That's how accountability and hope can exist together.
My Verdict: Luke Didn't Save Jess. He Helped Jess Find His Way.
Milo Ventimiglia's recent anniversary interview reminded me of how unusual Jess's character arc was for a teenage troublemaker.
When he first arrived in Stars Hollow, he seemed almost determined to fail.
He rejected authority.
He made enemies.
He skipped school.
And he behaved badly toward people who cared about him.
I wouldn't minimize any of those decisions.
But I also wouldn't have concluded that he was destined to remain that way.
And I'm glad the writers didn't, either.
Jess's eventual success wasn't simply the result of Rory believing in him.
Nor was it proof that Luke knew exactly how to raise a troubled teenager.
Luke made mistakes.
Rory made mistakes.
And Jess made plenty of them.
But Luke provided a home, expectations, and a relationship that Jess eventually came to appreciate.
Rory recognized his love of books.
And Jess ultimately had to decide what he wanted to do with his life.
By the time he became a writer and found work in publishing, he had begun using his abilities instead of wasting them.
I think that's a much more satisfying ending than simply pairing him romantically with Rory.
A teenager shouldn't have to win back a former girlfriend to prove he's grown.
He should be able to build a decent life for himself.
And Jess did.
I'm not suggesting that every teenager who drops out of school will become a published author.
Most won't.
Nor am I suggesting that parents should tolerate serious misconduct while waiting for a child to mature.
Children need guidance, boundaries, and appropriate consequences.
But they also need adults who understand the difference between a bad decision and a permanent character flaw.
A seventeen-year-old who behaves badly isn't necessarily showing us the person he'll be at thirty.
He's showing us who he is at seventeen.
And while we have to take that behavior seriously, we shouldn't automatically assume he has nothing better to offer.
At fifty-one, I think one of the most discouraging things adults can do is convince a young person that improvement won't change anyone's opinion of him.
If the child is always going to be the troublemaker, why bother trying to become anything else?
Luke gave Jess a reason to believe their relationship could survive his mistakes, even when the two couldn't continue living together.
And Jess eventually gave Luke a reason to be proud.
I don't know how many teenagers would return years later and thank the adult who spent so much time arguing with them.
But I imagine it would mean an awful lot to the adult who kept trying.
That's the part of Jess Mariano's story I appreciate most.
Not the leather jacket.
Not the sarcasm.
And not the endless argument about whether Rory should have chosen him.
It's the fact that a boy who initially seemed determined to reject everyone eventually became capable of recognizing the people who had helped him.
He found a direction.
He learned to work.
And he discovered that having a difficult beginning didn't mean he was incapable of building a worthwhile future.
Hold teenagers responsible for what they do. But don't decide their entire future based on who they were during the worst years of growing up.
Jess Mariano wasn't an easy child to raise.
He wasn't always a good boyfriend.
And he wasn't a model student.
But he wasn't a lost cause.
Luke saw enough in him to keep caring, even when he didn't know how to help.
And years later, Jess gave his uncle something better than an apology.
He gave him evidence that all that effort hadn't been wasted.
I'd say that's a pretty good reason to keep believing young people can change.
