'%20x='0'%20y='0'%20height='100%25'%20width='100%25'%20%0A%20%20%20%20%20%20%20%20%20%20xlink%3Ahref='data:image/jpg;base64,/9j/2wBDAAYEBQYFBAYGBQYHBwYIChAKCgkJChQODwwQFxQYGBcUFhYaHSUfGhsjHBYWICwgIyYnKSopGR8tMC0oMCUoKSj/2wBDAQcHBwoIChMKChMoGhYaKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCgoKCj/wAARCAAGAAoDASIAAhEBAxEB/8QAFgABAQEAAAAAAAAAAAAAAAAAAAUG/8QAIRAAAgICAQQDAAAAAAAAAAAAAQIDBAARIQUGEjFBYYH/xAAVAQEBAAAAAAAAAAAAAAAAAAACBP/EABkRAAIDAQAAAAAAAAAAAAAAAAECAAMRMf/aAAwDAQACEQMRAD8AwtW1a61LCkczweQm4ZvMNyxXex8DQ/PRyPZ7guU7EtaSvAzwuY2YNwSDon19YxiFFe5kre51VSD0T//Z'%3E%3C/image%3E%3C/svg%3E)
It’s 2025, and somehow, Gilmore Girls still feels like a warm hug on a rough day. Whether you’re watching it for the first time or rewatching for the tenth, there's something timeless about Stars Hollow’s quirky charm, Lorelai’s caffeine dependency, and, of course, Rory’s rollercoaster of a love life. But here’s the thing—every time we revisit Gilmore Girls, one age-old debate pops up louder than Kirk at a town meeting: What was up with Rory’s boyfriends?
Back in the early 2000s, they all had their fans. Some swooned for Dean’s boy-next-door vibe, others fell hard for Jess’s tortured artist aesthetic, and a few were seduced by Logan’s silver-spoon swagger. But now that we’re older, it’s time to re-evaluate these guys with fresh eyes. Do they still hold up? Or do they make us want to yell “Nooo, Rory!” at the screen?
So let’s take a walk down Gilmore Girls memory lane and unpack how Rory’s boyfriends fare in the year 2025 - for better, or for much, much worse!
Which of Rory’s boyfriends actually aged well in Gilmore Girls?
1) Dean Forester: Mr. First Love...with a jealous streak
Dean started out strong in Gilmore Girls. He was tall, sweet, and thoughtful—the kind of high school boyfriend who builds you a car...a literal car! He seemed like every parent’s dream, and for a while, he was. But upon rewatching, you start to notice the control issues—the way he panicked when Rory didn’t say “I love you” fast enough, the way he got territorial around Jess, the way he guilt-tripped her, even when she wasn’t in the wrong.
Then there’s the messier stuff, like sleeping with Rory while married to someone else. Yikes! For a guy who once seemed so wholesome, Dean's insecurity and jealousy really don’t sit well now. What used to feel like romantic passion just feels like possessiveness in hindsight. He aged like that milk you forgot was in the back of the fridge. It started off nice and smooth...and now it’s just sour!
2) Jess Mariano: The broody bad boy who actually grew up
Now let's talk about Jess—the brooding, sarcastic, book-loving rebel who sauntered into Stars Hollow and turned everything upside down. Back in the day, he was a walking cliché—leather jacket, daddy issues, and a total inability to talk about his feelings. He ghosted Rory, clashed with everyone, and made more excuses than progress. Not exactly a healthy partner.
But the twist? He grew up. Jess returned in later Gilmore Girls seasons - calmer, wiser, and way more emotionally intelligent. He apologized for his behavior, found a meaningful career, and never pressured Rory. Instead, he encouraged her dreams and respected her choices. Unlike the others, he didn’t try to insert himself back into her life romantically - he just showed up, did better, and left the door open. He aged like a quiet, dusty bottle of wine you forgot you had - and when you finally open it years later, it’s better than you remembered.
3) Logan Huntzberger: The rich kid with a soft center and slippery morals
Logan was everything Rory wasn’t used to in Gilmore Girls—wealthy, bold, and adventurous. He introduced her to a glamorous world of secret societies and last-minute trips to exotic places. He was charming and quick-witted, and unlike Dean and Jess, he could actually keep up with Rory’s intellect. Their chemistry was undeniable, and he pushed her out of her comfort zone in ways that helped her grow.
But here’s the problem - Logan never really outgrew his “I don’t do commitment” phase. He cheated, bailed on emotional conversations, and in Gilmore Girls: A Year in the Life, he was engaged to someone else while still sleeping with Rory. That’s not misunderstood complexity; it’s just poor decision-making. He aged like a fancy cocktail you’d order once - exciting at first, but as you sip more, you realize it’s mostly sugar and bad choices!
4) Marty: The ‘nice guy’ who couldn’t take a hint
Marty, aka “the naked guy” from Rory’s Yale days, seemed like a sweet underdog. He was funny, kind, and clearly had a crush on her. But when Rory didn’t feel the same way, he pulled a classic "nice guy move"—disappearing the moment she chose Logan and re-emerging later in the most awkward way possible.
When he showed up again in Gilmore Girls, not only did he pretend like nothing happened, but he also acted weirdly shady about his girlfriend. The vibe was off, and the more you watch, the clearer it becomes: Marty was only nice when he thought he had a chance. He aged like that one college hoodie you thought was comfy, but now just feels kind of sad and clingy.
5) Paul: The running gag who deserved better
Paul was Rory’s blink-and-you’ll-miss-him boyfriend in Gilmore Girls: A Year in the Life, and honestly, that was the whole joke. Rory keeps forgetting to break up with him. Everyone forgets who he is, and even we forget he exists. He seems like a genuinely good guy - polite and reliable. But Rory's total disinterest in him wasn’t just a punchline. It reflected how checked out she was emotionally, and how poorly she treated people she wasn’t invested in.
Paul didn’t do anything wrong. But that’s kind of the issue - he didn’t do much of anything at all. He was a placeholder, not a partner. He aged like a blank journal you bought with good intentions but never wrote in. Perfectly fine, just...irrelevant.
6) Tristan Dugray: The original troublemaker with untapped potential
If you blinked during Season 1 of Gilmore Girls, you might’ve missed Tristan—but this rich, smirking Chilton bad boy made quite an impression. He flirted, teased, and definitely carried major early-2000s heartthrob energy. He was the guy who called Rory “Mary,” made grand gestures, and looked like he walked off a CW billboard.
But when you peel back the charm, Tristan was mostly all show and no follow-through. He wasn’t around long enough to evolve, and his biggest trait was making Rory uncomfortable in a “I don’t know how to say I like you” kind of way. Watching it now, it feels more like pestering than flirting.
That said, you can’t help but wonder what could’ve been. He had the potential for a Jess-level arc if he’d stayed longer. Maybe military school made him grow up? We'll never know! He aged like a MySpace profile - iconic for the era, fun to revisit, but not someone you’d want to date now.
Trending
Time has a way of reshaping how we see our favorite characters, and Rory’s boyfriends are no exception. Some of them stayed the same, some got worse, and a few surprised us with unexpected growth. So the next time you're sipping coffee while watching Gilmore Girls and debating “who was best for Rory,” remember—it's not just about who made your teenage heart flutter, it’s about who actually grew up.
Reply
