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We meet Dean Forester in the very first episode of Gilmore Girls, and he and Rory quickly hit it off. He becomes her first serious boyfriend (which terrifies both Lorelai and Luke), and throughout the beginning of their relationship, Dean is sweet. However, fans agree things take a turn for the worse once Dean becomes a more demanding partner — like pitching a fit when Rory doesn't say "I love you" back and not supporting her Harvard dreams.

It's only heightened by the arrival of Jess Mariano in season 2, and it doesn't take long for Dean and Jess to get into a literal fight at a house party. While the scene is incredibly tense, the main thing actor Jared Padalecki remembers while filming is being on pain meds because of an injury.

“I remember Milo [Ventimiglia] going like, ‘This is kind of ridiculous because you’re twice my size and I’m holding my own,'" he tells EW. Milo agrees, adding, "Jared is 6'4", I’m 5'10". There’s a difference in reach and weight between us. So I usually like to say what Dean had in size and reach, Jess matched in crazy.”

After Dean and Rory break up, Dean marries Lindsay Lister, but ends up having an affair with Rory during season 4 before ending his marriage. Throughout Gilmore Girls season 5, Dean and Rory attempt to rekindle their relationship before deciding to split for good.

During Gilmore Girls: A Year In The Life, Dean and Rory run into each other at the market where they shared their first kiss, and after reminiscing on the past, part ways to move forward with their lives.

While fans continually agree Dean is one of the worst Rory Gilmore boyfriends ("dear god i hate dean," one X user tweeted), Jared Padalecki maintains close relationships with the cast. He had a super sweet interaction with Milo Ventimiglia after the This Is Us star showed Jimmy Fallon an “I love Dean 4 Ever” sign attached to his Emmy nomination.

“Jared and I are really good friends,” Milo, a self-proclaimed member of Team Dean, says.

"Ohmigod @miloanthonyventimiglia our offices are SO SIMILAR!!" Jared says in an Instagram response. "TWINSIES! (Well, I don’t have an Emmy nomination, but I DO have a “Best Body” trophy that was worth every dollar @genpadalecki paid for it on Hollywood & Vine). Miss ya brother. Couldn’t be more proud of ya."

Jess Mariano has some serious walls up when he moves in with Luke during Gilmore Girls season 2, but he takes a very quick liking to Rory. Their initial friendship is built on books, and it becomes stronger when they realize how comfortable they are confiding in each other. The relationship experiences some hiccups when Jess crashes Rory's car, and when Rory kisses him at Sookie St. James' wedding in the season 2 finale.

As a member of Team Jess myself, I'm over the moon every time I get to season 3 during my Gilmore Girls rewatch (you know, after Dean and Rory split and her relationship with Jess begins). And apparently, I'm not the only one!

“I’m team Jess," Jared Padalecki tells US Weekly. "I admit it. I even told Milo. I’m totally team Jess.”

However, it might surprise you to learn Milo is not. "Jess was a child," he tells InStyle. "I think Jess had a lot of life to live. And I don't think he was quite set up the best way in his younger years — not having a father, not having a parent. He had to find his way on his own a little bit."

Jess' relationship with Rory is just as crazy in season 3 as it is in season 2. Jess learns he'll have to repeat senior year if he wants to graduate high school, but refuses to tell Rory, which leads to more than one fight between the couple. And after telling Rory he can't take her to prom, Jess leaves to find his father in Venice Beach (this concept was actually supposed to be a spinoff about the character called Windward Circle, but the series never got picked up). However, Jess briefly returns to Stars Hollow one last time to tell Rory he loves her, and to ask her to come to New York, which she refuses.

Jess arguably brings out the best in Rory during Gilmore Girls season 6, when he finds out she dropped out of college, asking the now-viral "Why did you drop out of Yale?!" and encouraging her to patch things up with Lorelai.

When he shows up to support both Luke and Rory in A Year In The Life, the exes have a friendly catch-up — but I'm convinced *that* final look means he wishes they were something more.

Logan Huntzberger enters Rory's life during Gilmore Girls season 5, when she begins her first year at Yale University. While they start off on the wrong foot, Rory and Logan grow closer after the Yale Daily News assigns her a story about The Life and Death Brigade (Logan's secret society), and she joins them for a weekend in the woods.

The two fall for each other, and while Rory is ready to date Logan, he initially tells her he's not interested in an exclusive relationship. However, he quickly changes his tune when faced with losing her, and they officially begin their relationship.

The Huntzberger family doesn't approve of Rory as a match, and to top it off, Logan's dad (a huge force in the newspaper industry) doesn't think she's cut out for the career. By the end of season 5, Rory's convinced Logan to steal a yacht with her, winds up in jail, decides to drop out of Yale, and agrees to move in with her grandparents — all within, like, 48 hours.

While some fans are convinced Logan is the best choice for Rory, Matt Czuchry admits there's no "perfect" match for our leading lady. “I think [all three of Rory Gilmore's boyfriends have] strengths and weaknesses, like we all do,” he says on an episode of The Talk. “And I think that the fun of the show is that you’ve got these characters who are flawed and had these great pieces and everybody debates who’s best for Rory because they feel different about their strengths and weaknesses that might match up.”

However, Gilmore Girls screenwriter Stan Zimmerman disagrees! “Even though I don’t approve of all his character’s choices in later seasons and the reboot, I’ll always be ‘Team Logan,’” he says in his book The Girls: From Golden to Gilmore.

Rory and Logan's relationship starts off rocky in season 6 when the couple decides to take a temporary break. But even after they patch things up, the rift deepens when Rory learns Logan slept with other women during what he thought was a permanent split. But when Logan is injured during a jumping accident with the Brigade, Rory realizes how much she loves him and rushes to his side to help take care of him.

Despite initially wanting to just be friends with benefits at the beginning of their relationship, Logan is head over heels for Rory by Gilmore Girls season 7 and proposes — but their relationship seems to end for good when Rory turns him down.

Like the rest of Rory Gilmore's boyfriends, we see Logan in A Year In The Life thanks to his affair with Rory (despite his engagement to someone else) — which costumer Valerie Campbell confirms means he's the father of her baby.