16 Moments That Made Us Fall In Love With Jess Mariano

It all started when I caught an episode or two as my older sister watched Gilmore Girls back in the early 2000s. I saw Jess Mariano and immediately decided I needed to watch the whole series. To say Jess is my favorite of Rory’s boyfriends is a glaring understatement—I’m a sucker for the “bad boy” with a big heart. Let’s put things in perspective. Rory had three serious, vastly different boyfriends over the years: Dean, Jess, and Logan. Clingy, jealous Dean was by far the worst—you will never convince me otherwise—I promise you. Logan had me charmed and I remember thinking “Hey, he’s not so bad! He’s good for grown-up Rory.” Except that he was actually kind of a rich boy snob. And Jess, while consistently embracing his cynical bad boy persona, had qualities that ultimately helped Rory mature and grow—I can’t say the same for Dean or Logan.

I decided to have a re-watch marathon of every episode Jess appeared in. Throughout seasons two and three with a sprinkling of appearances in seasons four and six, Jess played an integral part in Rory’s story. He had his broody, angsty, too-cool-for-school habits—but deep down, the guy loved Rory (and you can absolutely bet I cry whenever I think about that fact). In turn, I loved Jess. So without further ado and with only two weeks to go until Gilmore Girls: A Year In The Life, these are my favorite Jess Mariano moments.


Luke Pushes Jess Into The Lake
At this point, Jess is fresh meat on the show and he doesn’t exactly make a great first impression. But when Luke pushed him into the lake, we all knew it would become an iconic Gilmore Girls moment. And he deserved it.

Jess Fixed The Toaster
Rory calls Jess out on being a real-life Holden Caulfield and making Luke’s life harder when all he does is stick up for him. Later, the diner’s “big toaster” is magically fixed. Even though Jess denies fixing it, he and Rory share a glance—it’s one of the first times we see Rory having a positive influence on him. Holden Caulfield or not, Jess takes one angsty step in the right direction here.

Jess Outbids Dean On Rory’s Basket
One more instance where Dean is literally a loser. Jess outbid Dean to not only win Rory’s company over lunch, but also to piss off Dean. I mean, Dean gets riled up so easily over something so insignificant. I’d poke that sleeping bear too. Rory makes a point to ask Jess why he’s only nice to her and, in true Jess fashion, he dodges the question. He likes her company and I’d argue she likes his too.

Jess Cleans The Gilmore’s Gutters
This is a seemingly minor event, but at this point, we know Rory is interested in Jess. After an awkward encounter inside with Lorelai, Rory leads Jess outside and tells him that if he cares about her at all, he’ll try harder to get along with her mom. And he does try. And it’s adorable. Because Stars Hollow’s very own Holden Caulfield cares.

Jess Brings Rory Food From Luke’s
Rory finally has the house to herself for a night, so she makes big plans, studying and doing laundry—it sounds like my kind of evening TBH. Paris crashes her plans and then Jess shows up with enough food “from Luke” to feed a small country. Rory’s plans go awry with all the extra company, but we see Jess get into heated discussions with Paris and later find out that Luke had nothing to do with that food delivery. Sneaky Jess…

Rory Tutors Jess
Jess only agrees to get tutored because he knew Luke asked Rory to help. I love how it’s no surprise that they get next to nothing done and instead have a little heart-to-heart about why Jess doesn’t try in school, what he wants to do in the future, and what Rory plans to do in the future. Rory knows he’s intelligent, that he has massive potential, and she likes that about him.

Rory Visits Jess in NYC
In an uncharacteristic move on Rory’s part, she ditches school to visit Jess in NYC. They eat hot dogs and visit an incredible record store together. On the surface, it’s cute—seeing them sharing their love for music and each other’s company. Sure, it’s not a great choice on Rory’s part and you could argue that Jess is negatively influencing her. But in her defense, it was a one time thing. All because Jess didn’t say goodbye.

Jess and Rory’s First Kiss
Something about not saying goodbye in NYC must have hit Jess hard and he returns to Stars Hollow, asking Luke if he can stay. He makes a sneaky cameo at Sookie and Jackson’s wedding, where Rory kisses him. I don’t love that it happened while she was still with Dean, but how could you not kiss that smug pout?

Turning Off “The Oasis” Sprinklers
After a summer apart and the two each being involved in other relationships, this is the first time we really get to see Jess and Rory interact. Rory is struggling to turn off the new neighbor’s sprinklers and wanders around town soaking wet, looking for help. Much to Rory’s dismay, Jess ends up stepping in before she can get ahold of Dean. Moments later, Dean is on his way and Jess turns the sprinklers back on so as not to start a fight between the two. It’s an oddly sweet gesture.

Jess Crashes The Dance Marathon
This is one of my all-time favorite episodes—the costumes, the makeup, the Jess antics, the overdue Rory/Dean breakup. It all starts when Jess shows up to the dance marathon with no intention of participating—just sitting around watching/reading/making out with his momentary fling. It pisses off Rory, which in turn pisses off Dean. After all, the breakup was inevitable—“He was right… about all of it.”

Episode One of Rory & Jess: The Early Years
The hi/bye exchange between Rory, Jess, Lorelai, and Luke at the diner following the big break up is delightful for so many reasons—I mean, this is the first time we’re seeing single Jess getting nervous around single Rory. It’s awkward and cute and brand new. I would so watch Rory & Jess: The Early Years… spinoff?

Jess Gets A Black Eye
This is more of a storyline than a moment, but I love every scene revolving around Jess’s mysterious black eye. Rory is instantly peeved and suspects Jess got into a fight with Dean. She can’t seem to let it go, even though Jess is actively trying to make a good impression on her grandmother at Friday Night Dinner. Jess eventually explains to Luke that he got attacked by a swan, which they then attempt to hunt down. At the end of the whole black eye/swan debacle, Luke tells Jess he needs to learn to communicate because “she picked you.”

Jess Returns To Stars Hollow
Over the year since Jess’s disappearance from Stars Hollow, Rory chops off her hair, starts school at Yale, and does a good bit of growing up. It’s no surprise that they eventually bump into each other in town, but what follows is huge. Jess finally tells her that he loves her. It’s a bittersweet moment (and a little selfish too, on Jess’s part). I totally disagree with how/when Jess went about telling her and how he ran off as soon as he said it. However, in Jess’s defense, I get it. I get why he ran. He was scared and I’d bet that was the most real thing he ever felt.

Jess Shows Rory His Book
Fast-forwarding through Rory dropping out of Yale and Rory not speaking to Lorelai for arguably TOO long, Rory and Jess quietly reunite (literally). They have a conversation and Jess shows Rory the book he wrote. I love this moment because she’s floored—she always knew he could do it. Cue the tears when Jess tells her he couldn’t have done it without her.

“This Isn’t You, Rory.”
Only a day after Jess gives Rory his book, they attempt to go out to eat and catch up at a normal volume. Logan crashes their plans and we see a hint of that old, jealous Jess come back. But given how much time has passed and how much he has grown, I think Jess gets fed up because Logan is being a drunk asshole and he still cares so much about Rory. This is where my all-time favorite Jess moment happens—Jess calls out Rory for not being herself, “I know you better than anyone. This isn’t you.” She’s living at her grandparents’, she’s involved with the DAR, she dropped out of Yale… and she doesn’t have an answer. She knows he’s right. And I truly believe that the reason Rory returns to Yale and speaks to Lorelai again is because Jess called her out on her bullshit. Nobody else could have that effect on her. She sees Jess has grown up, has become a published author—and it hits her hard.

Jess And Rory In Philly
Rory shows up to the publishing house in Philly where Jess works and is hosting a reading of some sort. When things quiet down, they have a conversation and he eventually kisses her. Rory snaps out of the moment and tells Jess she’s still with Logan, to which Jess tells her he doesn’t deserve to be treated this way. The dude grew up and he beat Rory to it. That’s my kind of character development.


Really, I could go on and on about my favorite Jess Mariano moments. This time around though, I admittedly caught more moments that painted Jess in a not-so-great light. Aside from being cynical and moody, Jess was frequently unreliable—and used to getting his way. The guy isn’t perfect. At the very least, I think we can all agree he had good intentions and serious feelings from the start, he just didn’t know quite how to express them until it was too late. But with time comes change and growth, so here’s to more memorable moments with Jess (and Rory) in the Gilmore Girls revival!

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