The air is getting colder, and the leaves are starting to change, so you know what that means? It’s Gilmore Girls season. Every weekend the iconic theme song, “Where You Lead” by Carole King and her daughter Louise Goffin, is playing from my laptop. It truly is the perfect show for autumn with all the small-town vibes…and the fact that Stars Hollow takes the season super seriously.
It’s no secret that Rory Gilmore got plenty of male attention. There’s the dramatic love triangle between her, Dean, and Jess—and then you add in Logan later on and it’s just one big mess. Not only for her, but even within the fandom. Many arguments have happened over who the better boyfriend is. Even Tristin has become a part of the conversation, and they didn’t even date! The truth is, we all gravitate toward different Rory “boyfriends” for a reason. Whether you’re Team Dean’s stability, Team Jess’ intellectual spark, Team Tristin’s charisma, or Team Logan’s adventure, your pick reveals something about your own relationship values and what you prioritize in a partner.
Dean
Let’s start at the beginning. Dean Forester was the first, showing up early in season one. He and Rory were together on-and-off for the first three seasons, even reuniting in season five after Dean’s marriage to Lindsay imploded—with Rory’s help, of course. He was the epitome of the “perfect first boyfriend”— thoughtful, attentive, and devoted.
If you’re Team Dean, you likely appreciate a partner who is caring and nurturing, and you value stability and security in a relationship. You’re drawn to the classic small-town romance and prefer being comfortable over chasing excitement. However, this might also mean you overlook warning signs like possessiveness or controlling behavior. Remember Dean’s jealousy over Jess with the constant phone calls and the public fights? And then there’s the season five affair—Dean cheated on his wife with Rory, yet somehow, she became the villain in his narrative. If Dean is your favorite, you might prioritize comfort so much that you rationalize red flags in pursuit of that safe and familiar feeling.
Tristin
Even though he was never officially Rory’s boyfriend, Tristin Dugray remains a part of the conversation for two reasons: he’s played by Chad Michael Murray, and the chemistry was undeniable. Their hallway banter and his persistent “Mary” nickname created tension that many fans wish had been explored further.
If you prefer Tristin, you likely enjoy a charismatic and playful partner who keeps you on your toes. You’re drawn to witty banter and moments of tension, favoring lighthearted fun over emotional depth. However, this could mean you sometimes overlook the need for deeper emotional connections. You may prioritize surface-level attraction and excitement over substantial growth or maturity in relationships.
Jess
Jess Mariano, seemingly the fan favorite, was the boy who stole Rory’s heart away from Dean. The stereotypical bad boy with a troubled past, Jess evolves throughout the series into a passionate and thoughtful individual who actually gets his life together—something Rory herself struggles with.
If Jess is your favorite, you appreciate complexity and growth in a partner. You’re attracted to the mystery and depth he possesses while drawn to his artistic spirit and love of literature. You enjoy intelligent, witty banter and value substance over surface-level charm. You’re an old soul, and people often say you’re mature for your age. You see potential in those who are misunderstood, believing in their best selves even when others have given up. However, you might also tend to romanticize emotional unavailability, mistaking someone’s inability to communicate for depth.
Logan
Finally, there’s Logan Huntzberger. When you think of Logan, you think of charm, intelligence, and adventure—all of which he delivers in spades. He introduces Rory to a world of spontaneity and luxury, pushing her beyond her Stars Hollow bubble.
Being Team Logan means you’re confident and adventurous. You appreciate a partner who is intellectually stimulating and encourages you to step out of your comfort zone. You’d accept his offer to jump off a cliff with an umbrella any day, and you basically have “in omnia paratus” tattooed on your forehead.
However, Logan’s charm comes with a darker side. His spontaneity often doubles as manipulation—pressuring Rory to prove herself worthy of his world by taking risks or feeling uptight for saying no. When he proposes in season seven, he gives her an ultimatum: marry him or it’s over. No compromise, no long-distance discussion—just an all-or-nothing demand that disregards her career ambitions. And in the revival, he maintains a secret affair with Rory while engaged to another woman, classifying it as a“what happens in Vegas” arrangement with zero accountability.
If Logan is your favorite, you might be drawn to partners who use confidence and grand gestures to mask controlling tendencies. You’re attracted to the thrill, but you may overlook how privilege and charm can become tools of manipulation. Look, Rory’s love life was a disaster—but it was our disaster to obsess over. The revival only proved that some people never learn (looking at you, affair with engaged Logan), but maybe that’s what makes it so relatable. We all have that ex we shouldn’t text, that ‘what if’ we can’t let go of, or that pattern we keep repeating. So, whether your Team Dean, Jess, Tristin, or Logan, own it. Your favorite says something about you—and unlike Rory, at least you can learn from her mistakes. Now if you’ll excuse me, I have seven seasons and a revival to rewatch before winter.