Jess was by far the best guy Rory Gilmore dated—if you don’t believe me, it’s scientifically proven. That being said, he was also a giant douche at least 50% of the time. But that’s all part of the Jess Mariano Experience. He’s a denim-jacket-wearing, Jack-Kerouac-reading contradiction. He’s not the guy who’s going to do things like “show up when he says he will” or “get along with your family.” That’s what Dean was for, and look how that turned out (weird, and with bad facial hair). Sure, Jess sometimes acts as bratty as a male version of Avril Lavigne, but he’s also mysterious, smart, and interesting. So when I say this is the best of Jess, sometimes I actually mean the worst, or the most annoying, or the most infuriating. In that spirit, here are the best moments from the black sheep of Stars Hollow, Jess Mariano.

2.10 “The Bracebridge Dinner”

When Lorelai and Sookie host a big dinner at the Inn, the whole town’s invited…including Jess. After Dean and his turtleneck sweater take off on a romantic carriage ride with his little sister, Rory thinks she’s stuck riding in a carriage for one. Until she gets an argumentative hop-on in the form of Jess Mariano. As everyone knows, carriage-rides are the perfect place to answer weird, kind-of-insulting questions about your relationship. As they ride through town, Jess asks what Dean and Rory talk about. Her answer—“Everything. Tons of stuff. Whatever.”—pretty much spells the beginning of the end for her relationship with Dean.

2.13 “A-Tisket, A-Tasket”

Stars Hollow, the town of too many festivals, has yet another event. This one’s a charity basket auction, where all the women pack lunch baskets and the men bid on them. Naturally, Dean plans to bid on Rory’s basket. What he doesn’t count on is Jess, who ends up outbidding him and winning a lunch date with Rory. That’s a bold move, even for Jess (or, as Taylor calls him, “the nice young hoodlum in the back”). Jess and Rory spend their auction-mandated time hanging out on the bridge, where she tells him to read The Fountainhead and he convinces her to give Ernest Hemingway another chance. Rory accidentally leaves the bracelet Dean gave her sitting on the bridge, and Jess pockets it (it’s a very Mr.-Brook-stealing-Meg’s-glove-in-Little-Women move). The two of them get pizza and go to a bookstore, which sounds like the best date in the history of the world. Later in the episode, Rory calls Jess, and guess what he’s reading? The Fountainhead, of course, while holding the Dean bracelet. This is probably the only romantic scene ever to prominently feature an Ayn Rand book.

2.16 “There’s the Rub”

Lorelai’s away for the weekend, and all Rory wants to do is spend a relaxing evening alone with her laundry and an impossibly large order of Indian food (Rory Gilmore knows how to do Friday night right). But then Paris shows up to study, and Jess shows up to put Rory and Dean’s relationship to the test, again. He comes bearing a giant care package full of food from Luke, who he says was worried about Rory being home alone. After Rory invites Paris to eat with them (Paris, excitedly: “I’m not allowed to have mac and cheese!…Do you have a 24 hour pharmacy in case I have an allergic reaction to something?”), Jess asks, “You think we need a chaperone?” Of course they need a chaperone! The sexual tension is so thick you could cut it with one Dean’s angry, dagger- like glares. Jess and Paris end up getting into a charming argument about Beat writers—Paris hates Jack Kerouac, Jess loves him. Paris claims, “Typical guy response. Worship Kerouac and Bukowski, God forbid you pick up anything by Jane Austen.” If there was a show called The Paris and Jess Hour and all they did was dish about writers and the proper dipping sauces for French fries, I’d watch that show in a hot minute. This scene is Jess at his best—flirty and weird and always ready to talk about books. This is why he was infinitely better than Dean, who sometimes tried to keep up, but never really could. Later in the episode, at the diner, Rory tells Luke thanks for sending over all the food. Luke has no idea what she’s talking about, of course…that food was all Jess Mariano’s idea. Rory and Jess share another typically flirtatious conversation, while DEAN LURKS OUTSIDE THE DINER AND WATCHES THEM LIKE A TOTAL CREEP. Things with Dean are starting to seem too much like a Lifetime movie where he snaps and keeps Rory in a cabin in the woods where no one can ever take her away.

2.19 “Teach Me Tonight”

Jess is in Big Trouble Mister (quoth Michelle Tanner) because he’s flunking out of school. But Jess is so whatevs about it, as is his way. When Luke threatens that he might have to retake 11th grade, Jess just says, “At least I’ll know where my classes are.” Zing. So Luke cons Rory into tutoring Jess. Predictably, their tutoring session doesn’t go so well. Jess literally does magic tricks. Does Jess have ADHD? Was that his problem the whole time? Did he just need some medication? Anyway, Jess is at his kind-of-jerky best in this scene, asking Rory where Dean is, asking her if she’s read Please Kill Me, quizzing her on Clash lyrics, and then asking if she wants to go get ice cream. On the way back from getting ice cream, Jess crashes The Car that Dean Built and Rory ends up in the hospital with a fractured wrist. It’s so unfair that something as perfect and innocent as ice cream can cause such pain.

2.21 “Lorelai’s Graduation Day”

Jess calls Rory all the way from New York City, where he’s been living in exile after what we’ll refer to as The Ice Cream Incident. He tells Rory he’s been hanging out in Washington Square Park, which is cooler than Central Park—“it’s the one where David Lee Roth got busted.” In a very non-Rory moment of adventurous abandon, Rory takes the bus to New York on the morning of Lorelai’s graduation. Luckily for her, Jess is reading a book right beside a sign that says “Washington Square Park,” so they end up getting hot dogs from a stand and going to a record store. Again, Jess knows how to plan a date. Who could possibly turn down hot dogs and records? Rory doesn’t get back in time for Lorelai’s graduation (which is her loss, because Sookie made a cake filled with 2 pounds of chocolate covered espresso beans), but spending the day with Jess was, in my opinion, totally worth it.

2.22 “I Can’t Get Started”

This episode is also known as The One Where Rory Kisses Jess. Rory’s just getting ready to walk down the aisle as one of Sookie’s bridesmaids when she spots Jess skulking around. She kisses him, and then runs away while telling him not to say a word to anyone about it. That’s the Rory Gilmore way…love ‘em and leave ‘em and then go to Washington for the summer.

3.7 “They Shoot Gilmores, Don’t They?”

This is my favorite Gilmore Girls episode of all time. Of all time! Stars Hollow has a 24 hour dance marathon because of course they do. There’s a lot going on in this episode–there’s Kirk being crazy and Taylor being weird and Sookie and Jackson having a fight—but most importantly, there’s Jess in the bleachers staring at Rory while creepily making out with his girlfriend. Eventually, Dean figures out what’s going on and removes himself from the picture. Not a moment too soon, if you ask me. When Jess finds Rory crying on the bridge, he asks her if she’s definitely broken up with Dean and then says, “I have to go take care of something now.” Because when you’re Jess Mariano, that’s how you break up with your weird girlfriend named Shane. You just “take care of something.” I really hope he didn’t murder her.

3.15 “Face Off”

All Rory wants is for Jess to ask her out on real dates instead of last- minute hangouts. Oh, Rory. Asking Jess to make plans is like asking the sun not to shine. As Jess himself says, “Rory knows I’m not the kind of guy who lives by a schedule.” You hear that? Jess Mariano makes plans for no man (or woman)! After not hearing from him for two days, Rory decides to go to a hockey game with Lane and her fake boyfriend, where she sees Dean with his new girlfriend (and future ex- wife!) Lindsay. Jess seems pretty terrible in comparison to Dean’s clean-cut reliability, but just when Rory’s at her breaking point, Jess shows up with tickets to see the Distillers. Okay, so she might not be able to count on Jess, but would Dean even know who the Distillers are?

3.19 “Keg! Max!”

Okay, so Jess is actually really terrible in this episode. He acts bored while Lane’s band is setting up (unforgiveable! Lane is a queen), acts like he’s cooler than everyone at the party, and then tries to have sex with Rory in an upstairs bedroom at weird Kyle’s house. Then he ends up getting in a huge fight with Dean on weird Kyle’s front lawn. Classic Jess. This episode is especially notable, though, for featuring my favorite Jess Mariano line ever. When Rory balks at having sex in an upstairs bedroom at weird Kyle’s house, she protests “But anyone could walk in!” Jess shrugs off her concerns with, “And Santa Claus could come down the chimney, whatever.” What a romantic— season 3 Jess is a grade A douche.

4.13 “Nag Hammadi is Where They Found the Gnostic Gospels”

While Rory’s in line for a burger at the Firelight Festival, who should appear but Jess. “I get to leave first!” she shouts, before running away from him. After he chases her through town, she spouts off a classic Angry-Rory speech: “You know, I have actually thought about this moment. A lot. What would Jess say to me if I ever saw him again? I mean, he just took off, no note, no call, nothing, how could he explain that? And then a year goes by. No word, nothing, so he couldn’t possibly have a good excuse for that, right? I have imagined hundreds of different scenarios with a hundred different great last parting lines, and I have to tell you that I am actually very curious to see which way this is going to go.” She’s speechless when Jess just says, “I love you,” before hopping in his car and getting the hell out of Dodge Stars Hollow. Jess and Rory are basically the worst about not waiting around to catch the other person’s reaction. It is just not polite to kiss someone or confess your love to them and then run or drive away. Have they no manners?

4.21 “Last Week Fights, This Week Tights”

After listening to Luke’s self-help tapes, Jess is moved to express his true feelings for Rory the only way he knows how—by showing up at her dorm and begging her to be with him. He barges in, leather jacket-ed and scruffy as all get out, and asks her to come with him. When Rory asks where, exactly, he plans on going, he shouts, “I don’t know! Away!” He tells her he’s changed, that she can count on him, and that they’re supposed to be together, but Rory doesn’t agree. And who can blame her for not suddenly deciding to drop everything and leave town? I mean, why does it have to be all or nothing? Hasn’t Jess ever heard of grabbing dinner and seeing if things might work out this time around? Is there no “just getting coffee and catching up” in the Jessverse? Maybe the self-help books should’ve taught him more about subtlety.

6.8 “Let Me Hear Your Balalaikas Ringing Out”

After Rory comes back to Emily’s after another terrible evening spent with Logan, guess who’s skulking around the driveway? No, not a drunken Taylor Doose (I wish). It’s Jess, of course! He’s living in Philadelphia now, and he says he wants to show Rory something. Unfortunately that’s not some sort of creepy sexual innuendo—Jess wrote a book, and he wants to tell Rory he couldn’t have done it without her. Oh, Jess. I take back all of those awful things I said about you! I don’t know what I was thinking. But when Rory and Jess are about to go out for a little catch-up dinner the next night, stupid Logan shows up and ruins everything. The three of them go out for dinner and Logan is, like usual, a total jerk, and not in the fun, sexual tension-y way Jess always was. After Logan insults him one too many times, Jess storms out of the restaurant. But before he hightails is out of town, he leaves Rory with the verbal smack down we all want to give her: “I know you better than anyone. This isn’t you. What are you doing? Living at your grandparents place, being in the DAR, no Yale… why did you drop out of Yale?” He also calls Logan a “jerk with a Porsche,” which is probably the most apt description ever. Oh, and he remembers Rory’s birthday. He might as well drop the mic when he walks away. And, as it turns out, Jess’s speech is enough to push Rory out of Emily and Richard’s brocaded nest. Thank God for Jess Mariano.

6.18 “The Real Paul Anka”

I can forgive this episode for its inclusion of April, whom I hate (I know she’s just a child, but I can’t help it. She ruined Luke and Lorelai!), because it features a kiss between Jess and Rory. After yet another fight with Logan (get it together, Rory—Logan sucks!) Rory goes off to Philly to see Jess at Truncheon Books. Jess is doing well for himself, which we know because he’s wearing a blazer. Some stuff happens, they talk, blah blah blah the point here is that Rory and Jess kiss. And then Rory has to ruin it by saying she’s still in love with Logan! Obligatory ugh: Ugh. “I can’t even cheat on him like he cheated on me,” she bemoans. Well, try harder, Rory. As she leaves, Jess says, “If it makes you feel better, you can tell him we did something.” Aw. Who says chivalry is dead? This is the last we see of Jess Mariano, but I like to imagine a world where he and Rory end up together, arguing about Ayn Rand and Ernest Hemingway for the rest of their lives.

Now it’s time for you to chime in with your own favorite moments. Let Jess Fest 2012 begin!!!!

About the Contributor:

Kerry Winfrey writes about YA for HelloGiggles, where she has a column called Young Adult Education, and she also blogs at Welcome to Ladyville. Kerry just happens to be a total swimfan for Gilmore Girls, so when she offered to share some of her scientific expertise with us, we immediately said yes, please and thank you (and pass the wine).

This post was written by a guest writer or former contributor for Forever Young Adult.