Gilmore Girls: The 20 Greatest Moments Of All Time

“Watching TV is companionable.

You share an experience.”

-Gretchen Rubin

It’s that time of year, folks.

It’s kind of like Lorelai with the snow. When I “smell fall”, I’ve just gotta rewatch the entire show. Something about leaves and sweaters and warm drinks makes me need all things Gilmore immediately. Am I alone?

Didn’t think so. Now put on your sarcasm and a big smile. We’re headed home to Stars Hollow.

Get cozy and let’s relive 20 of the greatest Gilmore Girls moments of all time.

1. “Unwashed Boys” (S3, E14)

Oh, Mrs. Kim, you and your hilariously judgmental ways. Thank you for entertaining us with your ability to openly call people out with no regard for their feelings whatsoever.

When she said “unwashed boys” I laughed so hard. Like, so. hard. No shame.

2.  Cat Kirk (S3, E9)

Human Kirk. Cat Kirk. All the Kirks. How will we keep up?

It’s just another glorious day in Stars Hollow when Kirk hides in a bathtub full of water from his evil name-sharing cat, Kirk.

3. “I’m All In” (S5, E3)

Oh Luke, we love you, and maybe never more than this moment.

He’s all in and he’s not afraid to own it… or the fact that he kept that horoscope in his wallet for all those years. He’s basically telling Lorelai, I’ve loved you forever… Sigh.

4. The Richard Painting (A Year In The Life: Winter)

Was it just me or was this the highlight of the Year In The Life trailers? “Isn’t it wonderful!” Emily exclaims with pride. It’s clearly ridiculous, but also very sweet.

Plus, how Emily insists she wanted it in those measurements just makes it all the better. All the paintings in the Gilmore house, as usual.

5. The Longing Look (A Year In The Life: Fall)

I admit it. I’ve rewatched this scene no less than 495 million times.

love Jess and I love Milo’s acting here.

Like, the look he gives Rory in this scene just says everything.

He loves her. He’s always loved her. She’s the one. He aches for her and misses her and needs her. This is for sure the best Jess moment in Gilmore history (at least to me). Just pure love.

6. When Rory Can’t Resist (S2, E21)

Rory literally can’t help herself. She hops on a bus and ditches school because she just has to see him after their oh-so-awkward-but-precious “hey,” … “hey,”… phone call. They say nothing and say everything in the process.

It comes down to this: she just couldn’t go the night without the sight of his face… and that says it all.

7. Hay There (S3, E1)

“One day it occurred to me: cows never wrinkle.”

Why thank you, Kirk, for that astute observation at job #984.

But, don’t worry, I’m sure your mother will happily use the rest of your tainted Hay There product line. Too bad it was so hazardous it couldn’t even be thrown in the public trash.

Stars Hollow missed out on a true gem.

8. “Will You Just Stand Still?” (S4, E22)

Luke brings flowers.

Apparently, and not surprisingly, his first time ever to bring someone flowers. He’s sweet and attentive. He doesn’t even wear his hat (this is big stuff, people). He gets jealous when Max shows up and calls her out when he thinks that she’s not single.

He takes charge of the situation and finally, finally, we get to see them kiss.

In his typical gruff-but-lovable Luke way, it happens with the straightforward words, “will you just stand still?” Andddd… we swoon.

9. All The Dancing & All The Jealousy (S3, E7)

Sorry (not sorry), Team Dean. When you’re literally in the arms of someone, but can’t keep your eyes off someone else, that should be clue number one it’s just not meant to work.

I love how jealous Rory gets watching Jess and how Jess just continues to sit and stare, half out of curiosity and half just to bug her. It’s fabulous.

“So you can’t control when you look at me, but you have to force yourself to look at him?”

Oh, Jess.

10. “Come With Me” (S4, E21)

This moment, y’all. “I just wanted to see you… to talk to you. Come with me. Come with me… away. Do it, come with me, don’t think about it… you know we’re supposed to be together.”

I love tender Jess. He’s such a sensitive soul inside that tough shell, and he’s pleading with her knowing she can destroy him with one word. (I’m still mad at Rory for that “no,” by the way).

Then his face when she rejects him… Oh. My heart.

11. Lorelai Tells Rory The Harsh Truth (S4, E22)

This whole episode is an emotional roller coaster and half the time we just don’t know what to feel. In fact, it’s so many firsts we just can’t take it after a while.

Of course, one of them is the infamous first real blowout between Rory and Lorelai. But as painful as it is to watch, there’s still so much good in this scene.

The best moment is when Lorelai tells Rory the (very ugly and hard to hear) truth. While Rory may not be ready to hear it, deep down she knows her mother is right.

And don’t we all need that one person in our lives who loves us enough to give us the painful truth from time to time? It’s hard and real and just brings out all the emotions at once.

12. Paris & Doyle Practice Getting Their Groove On (S7,E9)

“Doyle and I will be scorching the floorboards.”

Ohhh yes. Let the insanity begin.

In typical Paris-like fashion, she and Doyle over-prepare for a 2002 themed party by rehearsing their dancing skills.

And it. is. pure. absolute. gold. I will forever associate Nelly with the burned-on image of Paris and Doyle learning to get their groove on.

13. What’s Meant To Be Will Be (S7, E22)

“I just like to see you happy.”

As if we weren’t already bursting with love for Luke…  now he spends all night sewing that makeshift tent and we’re just officially done.

After a rough season, we definitely deserved this moment just for suffering through. Thank you, pregnant Sookie, for ratting him out and making this possible.

Also have to throw out an honorable mention to Babette and her Morry sandwich line! There’s a mental image that just won’t quit. (No, really. Please quit.)

14. Rory & Jess Kiss At Sookie’s Wedding (S2, E22)

That moment. When Christopher moves aside to answer his cell and Rory sees Jess. You know, just casually standing near the base of the tree with all the flowers in the background.

Then they just stare at each other for a moment. Ahh. It just feels like spring for the soul, all fresh and new and lovely.

They talk (super briefly) and she lunges and that’s that. Call it chemistry, addiction, passion, or fate… these two just can’t stay away from each other. I call it adorable.

(And as a side note… this whole episode is crazy, am I right?)

15.  Loreali Professes Her Love Via Song (S7, E20)

That instance when you let your guard down and all the feelings and emotions and longings you’ve had bottled up inside you come out all at once… that was this moment.

It went from quirky and funny to serious and bittersweet in a heartbeat.

The best part to me was Luke’s reaction and face. That exact moment when he looks down and then back up. I CAN’T EVEN.

It was kind of like when you’re at a wedding when everyone turns to look at the bride, but you watch the groom instead and it’s precious.

All the feels on this one. #iwillalwayslovethisepisode

16. Emily Is So Proud It Brings Her To Tears (S2, E21)

Watching this moment, I’ve gotta say, I couldn’t help but feel like this one was a long time coming.

Like years ago, Richard and Emily should’ve been watching their little girl graduate and beaming proudly. Even Rory not being there felt (weirdly) a little right to me, as if it was something Lorelai and her parents should be celebrating alone.

Somehow, it all came full circle here.

We all know the strain of Emily and Lorelai’s relationship (and I do mean strain), but this scene will be enough to choke you up despite it. Emily is so proud it brings her to tears and Lorelai is so proud that her mother is proud she cries as well.

For a moment, they stop snipping and bickering long enough to just love each other… even though it’s clearly a (beautiful) surprise to them both.

17. “I Know You Better Than Anyone” (S6, E8)

“I know you. I know you better than anyone. This isn’t you.”

Truer words have never been spoken. Jess so clearly gets Rory on a level no other man ever has– and I love how he isn’t afraid to call her out.

We all know Rory has hit a hugely rough patch here (can I just stop momentarily to say Logan is the worst), but Jess challenges her to be better– for herself.

He always helps her to still be her, but to be the best version of her. He’s the only one who can open her eyes to that truth and knows her in a way she may not even know herself.

“Happy birthday, by the way…”

Okay. So let me get this right. She hasn’t talked to you in forever. You just got done having a huge fight. This is pre generic Facebook reminders… and you remember her birthday anyway?

Anyone who doesn’t love Jess Mariano after this may want to reevaluate their life now. Just sayin’.

18. Luke Takes Loreali On A Real Date (S4, E21)

“For love is the greatest toy around, around, around…”

The wedding! The ridiculous Renaissance wedding with all the emphasis on the tights by TJ. The ceremonial sword. The not-so-funny vows. The adorably dressed Luke and Lorelai.

The whole time, all we can think about looking at them is how we can’t wait till it’s their wedding. And then there’s that glorious song they dance to. It’s all perfection from start to finish.

19. “I Couldn’t Have Done It Without You” (S6, E8)

Quick poll. Can you think of anything more amazing than the man you love telling you you’re his inspiration, muse, and basically his everything?

And not only did you inspire him, but he actually followed through with that feeling and did something incredible with it?

Nope? Me either.

(I’m sure you’ve caught on by now, but have I mentioned I’m Team Jess?! Every second of every day of my life, people. Every. Second.)

20. Jess Grows Up (S6, E18)

Am I the only one whose heart couldn’t help but swell here?

We always knew Jess had good inside of him, but he was young and hiding behind a very immature, guarded front.

Now, he’s all grown up and professional and accomplished.

Also, wearing a blazer. Who knew Jess would ever even own a blazer?

He repays Luke and thanks him. He’s genuinely interested in Rory’s life and (tries) to make sure she’s available before making a move. He’s understanding and good to her when most guys would turn into a jerk.

He’s just so stable and mature and loving it’s hard not to love him too.

But that’s okay. Love him. We all do.

So, that’s my list.

What’s your favorite Gilmore Girls moment?

Until next time, lifers.




For those who are curious, my top four, in order, are:

1) Jess,

2) Luke,

3) Rory,

4) Kirk.


Honorable Mention goes to Gil.

All photos © to WB.


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