I jumped on the Gilmore Girls bandwagon in 2020 in the midst of COVID-19, and to say I’ve been obsessed is merely an understatement. I’ve rewatched the series upwards of twelve times, which I believe grants me some authority on the subject of Rory’s suitors throughout the seven seasons of Gilmore Girls. While the heart of the show undoubtedly lies in Lorelei and Rory’s mother-daughter dynamic, their romantic suitors are equally vital to the show’s narrative.
Over seven seasons, Rory’s love life provided us with a spectrum of memorable (and some less memorable) suitors. I generally consider myself open-minded and non-confrontational, but when it comes to Gilmore Girls, I have some opinions I’m ready to defend over a coffee chat any day!
5. Marty
In last place, we have the sweet, nerdy, and genuinely kind Marty. His unrequited crush on Rory when she first came to Yale was cute to follow, but I think we can all agree that, as the audience, they were strictly platonic. Though he was a good guy, his storyline felt more like a plot device than a genuine romantic arc in the series. He was just a decent guy, just in love at first, but after coming back a few seasons later, pretending not to know Rory while dating her friend Lucy left a sour taste overall.
Best Moment: Genuine kindness during Rory’s first year at Yale
Worst Moment: Telling Rory she’s beautiful and flirting with her while he was dating someone else
4. dean
In my mind, there are two Deans. The first Dean was attentive, supportive, and seemingly devoted to Rory in the first two seasons. Their relationship was sweet, innocent, and filled with all the awkwardness and charm of teenage romance. When Jess started to be introduced as a leading male love interest, I also don’t blame him for being a little delusional and obsessive, as I think we all would too.
But in later seasons, his possessiveness, initially mistaken for affection, morphed into controlling behavior. The ultimate conception of his affair irrevocably damaged his character and painted him as someone who couldn’t respect boundaries or learn from his mistakes, which is why I simply cannot put him higher than number four. He became a symbol of what Rory had outgrown, a reminder of a simpler time that no longer fit into the life she was bound to live.
Best Moment: Building Rory a whole car
Worst Moment: Literally cheating on his wife…
3. Tristan
I don’t care that this is impractical! Tristan and Rory had too much wasted potential on the show. Their chemistry and banter were unmatched, and there was definitely potential for a relationship later down the line. Tristan’s presence added a layer of tension and drama to Rory’s Chilton experience, which I know we all loved to watch. While their relationship was primarily one of playful (and sometimes not-so-playful) antagonism, there was an undeniable undercurrent of attraction between these two.
Best Moment: Party scene sitting at the piano
Worst Moment: Giving Rory the “Virgin Mary” nickname at Chilton
2. logan
In my experience, the assessment of Logan Huntzberger routinely sparks contentious debate among Gilmore Girls enthusiasts. I will state this before I proceed: Logan Huntzberger is not a character this writer finds appealing.
Logan challenged Rory and pushed her out of her comfort zone in many beautiful ways. Their dynamic was complex, filled with intellectual sparring and emotional depth. The relationship itself was a rollercoaster, filled with highs and lows like any college couple.
What is different, in my opinion, though, is how Rory sort of molded into that private school, trust-fund lifestyle that Logan provided for her. He tended to be cocky, blatantly disrespectful, and sometimes even a borderline cheater. In my eyes, seeing other women when they first started to hook up was a big red flag for a significant other. Also, his proposal placed Rory in an untenable position, forcing her to choose between her aspirations and his expectations. I can understand why one would think he is the best love interest for Rory, but his inability to overcome his flaws leaves a lingering sense of dissatisfaction for me.
Best Moment: The rocket gift from The Twilight Zone
Worst Moment: His sister’s wedding when Rory found out he slept with almost all of her bridesmaids
1. jess
Was Jess the perfect guy? Definitely not. Was he Rory’s soulmate? Oh, absolutely. Their connection was built on shared intellectual curiosity, a love of books, and a quiet understanding. While their relationship was brief during high school, their connection remained palpable. Jess always understood Rory in a way the others didn’t, which is emphasized in the season six episode “Let Me Hear Your Balalaikas Ringing Out.”
By the time they both grew up a little bit, Jess went from a troubled teen to a published author, ready to finally commit to Rory. It was remarkable to watch him grow after his cold upbringing, and I would have loved nothing more for them to end up together. In my mind, the “Year in the Life” reprise ends with Jess and Rory living happily ever after (I’m delusional).
Best Moment: “Why did you drop out of Yale??” speech
Worst Moment: Leaving for California without saying goodbye
My verdict
Each relationship in Rory’s life served as a chapter in her that is the beautiful encapsulation of this coming-of-age show. While opinions on her suitors remain divided, their collective impact on Rory’s life is undeniable, shaping her into the independent and thoughtful woman she becomes (kind of).