A carriage-ride conversation and a demolished snowman. 

A restored pale-blue 1961 Dodge Lancer.

Typing 90 words per minute, saving the Daily News on a frantic night. 

Each a grand declaration of love, a gesture of affection with one aim–winning Rory Gilmore’s heart.

As we mark the 23rd anniversary of the beloved “Gilmore Girls” premiere, it’s only fitting to stroll down the streets of Stars Hollow, where Rory Gilmore’s (Alexis Bledel) journey through love continues to keep fans of the show captivated. 

Rory, the bright and bookish centerpiece of the show, might have attended the prestigious Chilton Academy and Yale University, but her real education is in matters of the heart. 

In honor of this milestone, we’re drawn back to the enduring debate that has raged among “Gilmore Girls” fandom for decades: Who was the most deserving, the most endearing, or perhaps the most intriguing of Rory’s real romantic interests? 

So, in the spirit of the fast-talking, mile-a-minute pop culture-referencing Gilmore girls, let’s spare no time and dive right into the world of Rory’s love life, one charming suitor at a time, ranking her three long-term loves who vied for Rory’s heart throughout the show’s seven-season run. 

Sorry, Tristan fans, we are only looking at her three season-long steadies. There is her first love, Dean Forester (Jared Padalecki), the figurative boy-next-door. Jess Mariano (Milo Ventimiglia) is the brooding bad boy, intellectual and sensitive beneath the surface. Then there’s Logan Huntzberger (Matt Czuchry), her borderline cocky college boyfriend, a trust-fund Yalie with a thirst for adventure.

In ranking Rory’s romances, we considered the chemistry between the couples, the romantic moments that made each relationship sparkle, each suitor’s personality and their long-term compatibility with the younger Gilmore girl.

Dean was a first-season fan favorite stumbling into Rory’s life (or technically, she stumbles into him.) He’s tall, handsome and that hair… He seems to get Rory’s pop culture references. Well, at least some of them.

He’s sweet–a hopeless romantic–celebrating the couple’s three-month anniversary by restoring a vintage car for the 16-year-old Rory. 

The chemistry between Rory and Dean is evident–at first. 

When Dean confesses his love for her, she doesn’t reciprocate. Rory isn’t ready to say those words–so the couple say goodbye–breaking up.

At least for a few episodes. 

Their relationship revs back up when Dean reveals despite the couple being broken up, he continues to build the car for Rory. 

Rory and Dean are on-again and off-again three times throughout the series because they truly lack common interests. 

She won’t shut up; he doesn’t have much to say. He is a jock; she is an academic. 

Rory doesn’t just read books; she consumes them. Over the course of the series, the character is shown reading just shy of 340 books.  

Books, movies, knowledge are core tenets of who Rory is. 

By the end of the series, Dean is working a dead-end job; he is a college dropout. 

While they live in the same town, they live in two different worlds.  

Jess Mariano comes from another world, moving to Stars Hollow to live with his Uncle Luke after his mother kicks him out. 

While he loses his mother’s affection, the brand-new bad boy wins Rory’s.

Jess and Rory share an intellectual spark, spending hours conversing over books, over life, over everything. 

The pair’s spark is so bright, even Dean can see it, as Rory and Dean break up for a second time because Dean recognizes the strength of the connection between Jess and Rory.

Their conversation comes easy. Rory finds him witty, clever, smart. 

And sexy. 

Jess is Dean’s foil; he doesn’t just read, he has read “Howl” over 40 times. He steals Rory’s copy and annotates it. Sharing his deepest thoughts. Dean, by comparison, once volunteered to watch Rory browse for books for “seven or eight” hours on end.  

Jess casts a long intellectual shadow over Dean. He is one of the first people Rory meets who can keep up with her. 

Their conversations are effortless, the repartee between the two flows like the coffee at Luke’s Dinner.

Jess offers Rory something she simply never had with Dean–an equal.

With Dean, Rory’s life is simple. Her small Stars Hollow world is charming and comfortable. Her experience at Chilton challenged her (and humbled her a bit at the start), Jess plays the same role in her life. 

Jess serves to inspire Rory. He empowers her, challenging her to make the future she dreams of–Harvard, Yale, Journalism, escaping Stars Hollow–a reality. 

Dean is “safe,” and safe is not sustainable in the long run. 

Jess is unconventional, and so are his acts of love: destroying a snowman so the Gilmore girls can win the Stars Hollow Snowman contest, stealing one of Rory’s books and annotating it–sharing his intimate thoughts with her, adding raunchy films to the shelves at Stars Hollow Video to spare Rory’s embarrassment (it’s a long story).

Jess works to make things possible for Rory, things impossible with Dean.  

The reason Rory returns to Yale after dropping out? Jess. He propels her forward.

Dean holds her back. Dean never truly let Rory go. Not when he is engaged to another woman, not when she is with Jess, not when he is married. 

Enter Logan Huntzberger, the stereotypical spoiled kid, thriving off of daddy’s name and daddy’s money (despite a hatred for his father). Slightly smarmy, slightly smug, with self-confidence bordering on cockiness, Logan is Rory’s most suitable partner.

While Rory’s college beau’s grand romantic gestures aren’t nearly as grand as Dean and Jess’s, Rory has grown beyond those things by the time she starts dating Logan at Yale. 

Logan is most romantic when he doesn’t mean to be, like when his fast typing hands effortlessly helped save the day and save Rory in publishing the Yale Daily News. He isn’t playing sweet or sincere. He isn’t acting like the bad boy, a tortured soul. He is authentic. 

The playful banter Rory had with Jess? That chemistry is there with Logan.

The safety Rory had with Dean? Well, Logan’s checkbook can provide some comfort there for the perennially cash-strapped Gilmore.  

Logan forces Rory to unwind and relax. Ever focused on school, honed in on academic achievement, excessively so at times, Logan’s happy-go-lucky attitude introduces Rory to fun, to adventure, to a college experience beyond the classroom or the newsroom or her bedroom studying.

Throughout the series, Dean ends things with Rory three times, twice in public. This, despite longing for her while with another woman, while married to another. 

Dean lacks the emotional maturity to be a true partner. He breaks up with Rory rather than wait for her to develop feelings of love. He marries a woman while in love with Rory. He enters into an affair with Rory rather than end his relationship with his wife. 

Dean is destructive, toxic and gaslights Rory before that term was popular. He tears at the fabric of the most constant relationship of Rory’s life–the one with her mom. 

Jess and Logan both understand Lorelai’s role in Rory’s life. 

Jess leaves town after wrecking Rory’s car, swerving to avoid an animal (yes, that car–symbolism) and fracturing Rory’s wrist. Lorelai is furious at Jess and viciously argues with his uncle about Jess’s impact on Rory. 

Jess, in a sense, swerves to avoid hurting Rory, her relationship with her mother, and her future–and leaves. 

Something Dean could never bring himself to do. 

Logan, too, sees Lorelai’s role in Rory’s life. Breaking from tradition and asking Lorelai for her daughter’s hand in marriage, not her ever-absent father Christopher. 

Rory says no–something she has never had the agency to do in her previous relationships. Something that she is only able to go because of her growth. Growth made possible by Logan.

Logan is undoubtedly Rory’s best boyfriend on “Gilmore Girls.”

From their initial meeting at Yale to their escapades with the Life and Death Brigade, Logan brings out a playful and spontaneous side in Rory that no other boyfriend could. He makes her more well-rounded. Instead of reading about adventures, she gets to live them. 

He challenged her intellectually, matched her wit, and supported her ambition without overshadowing her. 

Their relationship felt like a partnership of equals, making Logan the perfect match for Rory–something she lacked with her first two flames.