For die-hard Gilmore Girls fans, the Great Boyfriend Debate is about more than having a preferred suitor for Alexis Bledel‘s Rory Gilmore.

When stating your case for who should have ended up with Stars Hollow’s favorite daughter — be it Dean Forester (Jared Padalecki), Jess Mariano (Milo Ventimiglia), or Logan Huntzberger (Matt Czuchry) — your choice isn’t just an opinion. It’s a declaration.

Fans watched Rory traverse three major relationships across the series’s seven original seasons. And while Rory’s eventual romantic fate is decided by the series’s end, that doesn’t stop the question from being asked: Who should Rory Gilmore have ended up with?

As fans continue to find Gilmore Girls through streaming services and collector’s DVDs, the question perpetually gets a new life.

For the staunchest fans, what might be painful to admit is that at one point all three of Rory’s beaus were perfect for her, even if the “best one” is up for debate. But they represented more of a series of mirrors for Rory, revealing something about her journey that she couldn’t discover by herself.

Where do you start when sorting through the details of a beloved series’s most contentious debate? At the beginning, of course.

Team Dean?

Dean (Jared Padalecki) and Rory (Alexis Bledel) on ‘Gilmore Girls’.

The WB/ Greg Schwartz

In one corner you have Dean — the impossibly tall, brooding transfer student with dreamy hair and a deep voice.

Introduced in the first episode, the chance meeting between Dean and Rory lined up imperfectly with Rory’s acceptance to the prestigious prep school Chilton.

While Dean was an idyllic first boyfriend (He built her a car! He regularly joined Rory and Lauren Graham‘s Lorelai for movie night!), it’s hard to ignore that he represented something Rory would never be: comfortable.

As early as the season 1 episode “That Damn Donna Reed,” it was clear Dean wanted a wife. And when Rory pushed back, they grew further apart.

In the fan-favorite episode “They Shoot Gilmores, Don’t They?” Dean ends things, and yet, by the end of the next season, Dean takes Rory’s virginity…in her childhood bedroom…while he’s still married. Yikes indeed.

Perhaps worse, Dean never finds his place along Rory’s promising trajectory, always feeling like their relationship wasn’t in line with her Harvard aspirations. Even Jared Padalecki, who played Dean, has admitted that he’s on Team Jess.

Team Jess?

Jess (Milo Ventimiglia) and Rory (Alexis Bledel) on ‘Gilmore Girls’.

WB/Ron Tom/Warner Bros/Everett

Of course, Team Jess comes with its own complexity.

Jess Mariano, the bad-boy nephew of Luke Danes (Scott Patterson), drops into Stars Hollow in season 2 to upend Rory and Dean’s relationship and harass the townspeople to near insanity.

But the leather-jacket-toting, raven-locked dreamboat captured hearts as the misunderstood intellectual who matched Rory’s brilliance, squarely focused on a life of independence for both Rory and himself.

Did that also include Jess endearing himself to Rory before recoiling and ghosting? Sure.

Moody to the point of being cruel, the Jess character is too familiar. He’s somehow the boyfriend your mom warns you about while also being the boyfriend who makes you feel most yourself.

That tracks with Rory’s story. Despite Lorelai wanting success for Rory, it was Jess’s independent spirit and brutishness that often led Rory furthest from her roots. Remember when Jess persuaded Rory to take a bus to New York City, subsequently making her miss Lorelai’s graduation?

Still, Jess remained a favorite. He was the guy with promise, slowly inching his way to fulfilled potential.

Though Jess exited as a series regular at the end of season 3, he continued to periodically appear in Rory’s life to remind her of her own genius. Whether showing up after publishing a book or just to visit Luke, his refrain was consistent — he believed Rory was a contender until the very end.

Jess wasn’t particularly concerned with keeping Rory so much as he adored her.

Ironically enough, Milo Ventimiglia and Padalecki have been each other’s character’s biggest supporters, with Ventimiglia admitting that he is Team Dean, leaving Rory’s third suitor on an island of his own.

Team Logan?

Rory (Alexis Bledel) and Logan (Matt Chzuchry) on ‘Gilmore Girls’.

The WB/Patrick Ecclesine

First appearing in season 4, Matt Czuchry’s Logan Huntzberger was Rory’s longest ongoing relationship on the series.

Practically a gift from the upper-class gods, Logan was everything her grandparents wanted for her: wealthy, well-bred and handsome to boot. He also ticked all the boxes of whom Lorelai didn’t want for her daughter: privileged, smarmy and entitled.

The heir to a newspaper conglomerate — an ideal fit for Rory’s journalistic aspirations — served as the perfect conduit to show Rory (and, by proxy, Lorelai) what their lives could be in the context of the Gilmore social circle.

But even at her most enamored, Rory quickly realized that a family name and a try-hard attitude weren’t enough for the Hartford elite.

The Huntzbergers had a way of making Rory feel small, fueling some of her worst decisions on the series (see: stealing a yacht at the tail end of season 5, dropping out of Yale and joining the Daughters of the American Revolution).

All that aside, Logan was the man most committed to locking down Rory.

With a proposal at the series’s end, Logan fought to bring Rory into the Huntzberger fold, despite his family’s disapproval. And Rory never failed to rush to Logan’s side when he was in emotional (or sometimes physical) peril.

For Logan fans, nothing could be more romantic than a rocket ship, a man who calls you Ace and the promise of a happily every after.

There’s something about the options that makes the Great Boyfriend Debate such juicy, timeless fodder. Your choice of suitor is almost like an astrology sign, revealing something about the fans themselves.

In 2024, Kelly Bishop, who played Emily Gilmore, responded on TikTok that she’s Team Logan. Even as Ventimiglia pursued This Is Us and Czuchry settled into The Good Wife, journalists and fans alike still slid in the quick question…But what team are you on?

And maybe it’s not the three guys, but perhaps what they represent for Rory, that keeps the question on the tips of our tongues.

It’s not like these are the only three men who ever crossed Rory’s path. We’re not talking about Chad Michael Murray’s one-dimensional Tristan Dugray, are we? There’s no love for Marty (Wayne Wilcox), the lovable, reliable Yale classmate who seemed most in line with Rory’s upbringing. And don’t get us started on the shadow of a human named Paul (Jack Carpenter) whom Rory dated in A Year in the Life.

We only focus on the big three; the men who highlighted the most relatable evolutions of Rory Gilmore.

The truth is that each of her love interests pulled something specific out of her: for Dean, the innocence of a first love and the rejection of a simple life. For Jess, the rebellious intellectual at Rory’s core and the independence she needed to go it alone. And for Logan, the would-be fate of wealth and privilege that Lorelai so desperately wanted her and Rory to escape.

We love to choose a boyfriend and, by extension, choose our favorite version of Rory. I think the Great Boyfriend Debate is about what, not whom, Rory needed most.

But the struggle remains too fun to give up. Whether debating with a new fan who just finished their first binge or going to the mat with a veteran after a few glasses of wine, everyone believes they know best for Rory Gilmore. May the question remain: Who should Rory have ended up with?

At least we can all agree. The answer isn’t Paul.

A version of this story is available in a special print edition of Entertainment Weekly celebrating 25 years of the series. Find Gilmore Girls: The Classic Show Lives On wherever magazines are sold.