The Rory Gilmore Guide to Ruining Your 20s (and How Not to Follow It)

By Meet Dave

Growing up, I didn’t watch Gilmore Girls for Rory Gilmore. Honestly, I started watching because my best friend Ri was obsessed with it. But somewhere along the line, I got hooked. Rory had it all: the fast-talking wit, the intelligence, the seemingly perfect relationship with her mom, the academic drive. She was the dream student, the overachiever, the girl who always had her nose in a book but still somehow managed to have a social life. She was “that girl” before the internet made “that girl” an aesthetic.

But then she went to Yale.

And if you’re like me, you probably felt a mix of shock, frustration, and disappointment watching Rory unravel. The girl who once seemed untouchable started making choices that didn’t just not feel “human” but felt, honestly, kind of depressing. First, it started with dropping out of Yale. Then, dating Logan, who, love him or hate him, pulled her into a world she didn’t seem built for. Stealing a yacht. Losing confidence in her abilities. And all of a sudden, right in front of our eyes, Rory wasn’t the perfect, bookish role model anymore.

But here’s the thing: I think Rory’s slump actually made her even more relatable. If you’ve ever gone through your own version of a “Yale slump,” burnout, imposter syndrome, or that terrifying realisation that you’re not as special as you thought you were, then you know exactly what I mean. Rory’s story is more than just a TV character arc. It’s a mirror of what so many of us go through when the world finally catches up to us.

So let’s break it down: what exactly went wrong for Rory Gilmore, and how can we learn from her mistakes to avoid our own version of the “Yale slump”?

Being “the smart kid” doesn’t cut it forever

Rory’s whole identity was built on being smart. That’s who she was in Stars Hollow: the top of her class, the reader, the future journalist. Everyone hyped her up like she was the chosen one.

But then she got to Yale. And suddenly, she wasn’t so special anymore. She was surrounded by hundreds of other kids who were just as smart, just as driven, and maybe even sharper. And for the first time in her life, Rory was… average.

I’ve seen this happen in real life. High school “genius” hits college, realises everyone else got straight A’s too, and suddenly they don’t know who they are anymore. If all you’ve got is your brain, and you’re not the top brain anymore, you’ll collapse.

That’s what Rory did.

#Lesson 1: Don’t build your whole identity on being the best at something. Eventually, someone’s going to outdo you. Build it on who you are when you’re not winning.

Comfort is the enemy of ambition

Enter Logan. And with Logan, a shiny new lifestyle: parties, boats, rich friends, zero consequences. And for Rory, it was like stepping into cheat mode.

But here’s the problem with that: the more comfortable she got, the less she hustled. The Rory who used to stay up all night with flashcards was suddenly drinking champagne at country clubs. She stopped grinding, and the fire burned out.

I’ve seen this too. Guys getting that first paycheck, realising they can “coast,” and suddenly their dreams fade because Netflix and Uber Eats feel way easier than chasing big goals.

#Lesson 2: Comfort feels good, but it’ll kill your drive if you’re not careful. Don’t confuse cozy with fulfilled.

Don’t let one critic define your whole life

The turning point for Rory was when Mitchum Huntzberger, Logan’s dad, told her she didn’t “have it” to be a journalist. That one comment broke her. Instead of shrugging it off, she believed and internalised it.

I don’t care who you are; if you let one person’s opinion dictate your self-worth, you’re screwed. Rory had years of proof that she was a good writer. But the second Mitchum knocked her down, she folded like a cheap chair.

We’ve all been there. A boss, a coach, a professor tells you you’re not good enough, and you start to believe it. But here’s the truth: sometimes they’re wrong. Sometimes they don’t see the full picture. And sometimes, they’re just testing you to see if you’ll fight back. And Rory didn’t.

#Lesson 3: Criticism is inevitable. Use it, don’t absorb it. The second you let one hater define you, you’re done.

Quitting isn’t always smart

So what did Rory do after Mitchum’s critique? She dropped out of Yale. Classic panic move.

Now, don’t get me wrong, dropping out of school can work if you’ve got a plan. Plenty of people quit college to build something better. But Rory didn’t leave to chase her dream; she left because she was scared. She wasn’t running towards something; she was running away.

And when you do that, you drift. That’s exactly what she did: DAR events, living at her grandparents’ house, wasting time. She wasn’t finding herself; she was hiding.

#Lesson 4: If you quit something, do it with intention. Know what you’re moving towards, not just what you’re escaping from.

The slump is real, but it’s not permanent

Rory’s Yale slump is painful to watch, but here’s the truth: everyone hits one. College slump, career slump, life slump. The moment you realise you’re not invincible, you stumble.

What matters is what you do after. Rory eventually pulled herself back, refocused on journalism, started saying no to distractions, and tried to live on her own terms again. It wasn’t perfect, but it was progress. And that’s the real takeaway. 

#Lesson 5: The slump doesn’t define you unless you stay in it.

I used to get angry at Rory for not living up to her potential. But the older I get, the more I see myself in her. Her slump isn’t a failure of writing; it’s something we all go through. The burnout, the imposter syndrome, the drifting, it's just a part of life.

What matters is whether you wake up from the slump and course-correct. Rory, by the end of the series, does. She picks herself up, turns down Logan’s proposal (a bold move in itself), and decides to pursue journalism again. It’s messy, it’s imperfect, but it’s hers.

And maybe that’s the ultimate lesson. You can idolise Rory for being the “perfect student” all you want, but the real inspiration comes from watching her fall apart and then (slowly and stubbornly) put herself back together.

So how do you avoid a Rory Gilmore crash?

Here’s the short list I keep for myself when I feel like I’m sliding into a slump:

  • Redefine success. Don’t let your whole identity hang on one label (the smart guy, the athlete, the “funny one”).

  • Stay hungry. Comfort feels good, but it won’t push you anywhere.

  • Handle criticism like fuel. Take what’s useful, burn the rest.

  • Quit smart. If you’re stepping back, make sure you’re stepping toward something better.

  • Slumps aren’t the end. Everyone falls. The ones who win are the ones who get back up.

Final Word

Rory Gilmore’s Yale slump wasn’t just bad TV; it was the most real part of her story. It showed that even people who seem to have it all figured out can lose their way.

But here’s the deal: you don’t have to repeat her mistakes. Learn from them. Don’t collapse when you’re no longer the best. Don’t let comfort steal your drive. Don’t hand over your confidence to one critic. And when you hit your slump, and you will, remember that it won’t last forever if you don’t let it.

At the end of the day, Rory wasn’t perfect. And that’s exactly why her story matters.


Meet Dave is a Master of Commerce (Extension) student studying Marketing and Human Resource Management who occasionally writes. When he’s not pulling life lessons out of TV characters, which, let’s be honest, is most of the time, you’ll find him solving sudoku, doomscrolling, studying, or convincing himself he doesn’t need another coffee.


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