We picked the best Gilmore Girls episodes for all of your favorite relationships while you watch the show on Netflix

Team Jess vs. Team Logan: The Best Gilmore Girls Episodes for Fans of Every Relationship

October 02, 2014 / by / 282 Comments

This October marks an exciting time for any girl who attended junior high or high school in the early-to-mid-2000s. Crocs are ironically cool again, Hilary Duff is releasing a new album, and the facial burns from trying to straighten our 2004 Ashlee Simpson bangs have finally healed.

Like brace-faced caterpillars morphing into molly-popping butterflies, we’ve evolved from Sevvies to basic bitches. Instead of rocking Hollister polos and gauchos waiting in line to see the Jonas Brothers, we’re slipping on crop tops and leggings and waiting in line for our Pumpkin Spice Lattes. But one thing sure as hell hasn’t changed: we still fucking love Gilmore Girls.

As a fledgling adult, I have to say that (unpopular opinion alert) Jason is my favorite Lorelai boyfriend. He’s smart and witty and has amazing facial hair. He and Lorelai had the intellectual banter she never got with Luke, the chemistry she never got with Max, and the support she never got with Christopher. Honestly, if his D-bag father hadn’t ruined their relationship, they would have been perfect together. No matter what your favorite Gilmore Girls relationship is, though, there’s an abundance of episodes to experience all of your favorite moments. To make it easy on you, our wonderful readers, we have compiled some of the best episodes for each of your favorite relationships on the show.

Rory and Dean
For girls who Instagram their Starbucks on the first day of fall with #PSL #blessed #onmygrind

What a fucking meathead

Best Episode: Season 4, Episode 22, “Raincoats and Recipes”
Rory FINALLY fucking loses her virginity to her high school boyfriend even though he’s married to someone else now. For Rory and Dean fans, the crazy sexual tension is a delight to watch throughout the fourth season and it all comes to a head in this episode.

Honorable mentions:
Season 1, Episode 5, “Cinnamon’s Wake”
Season 1, Episode 7, “Kiss and Tell”
Season 1, Episode 9, “Rory’s Dance”
Season 1, Episode 20, “P.S. I Lo…”
Season 3, Episode 7, “They Shoot Gilmores, Don’t They?”
Season 4, Episode 14, “The Incredible Shrinking Lorelais”

Rory and Jess
For girls who worshiped Jack Kerouac and complained a lot when they cast Kristen Stewart in On The Road.


Best Episode: Season 3, Episode 19, “Keg! Max!”
This episode had everything a teenager could ever want. Red Solo cups. Hot makeout scenes. A lack of parental supervision. Although it was the last episode where Jess and Rory would really be a couple, we always knew he would be back. He couldn’t help himself.

Honorable Mentions:
Season 2, Episode 5, “Nick & Nora/Sid & Nancy”
Season 2, Episode 13, “A-Tisket, A-Tasket”
Season 2, Episode 19, “Teach Me Tonight”
Season 2, Episode 22, “I Can’t Get Started”
Season 4, Episode 20, “Luke Can See Her Face”
Season 6, Episode 8, “Let Me Hear You Balalaikas Ringing Out”

Rory and Logan
For girls with who stayed with their college boyfriends waaaayy too long

Still unclear if you’re an ass or not…

Best Episode: Season 5, Episode 7, “You Jump, I Jump, Jack”
Logan Huntzberger managed to take advantage of the only situation on the planet where buying a dress and asking a girl to wear it is remotely acceptable.

Honorable Mentions:
Season 5, Episode 8, “The Party’s Over”
Season 5, Episode 13, “Wedding Bell Blues”
Season 5, Episode 19, “But I’m A Gilmore!”
Season 7, Episode 21, “Unto the Breach”

Lorelai and Christopher
For girls who keep going back to their exes even though they’re actually fucking awful and get other people pregnant.

How can someone so beautiful be so terrible?

Best Episode: Season 1, Episode 16, “Christopher Returns”
Christopher’s leather jacket was Amy Sherman-Palladino’s gift to tweens and teens across America. I CAN’T EVEN.

Honorable Mentions:
Season 2, Episode 3, “Red Light On a Wedding Night”
Season 2, Episode 22, “I Can’t Get Started”
Season 3, Episode 15, “Dear Emily and Richard”
Season 6, Episode 22, “Partings”
Season 7, Episode 7, “French Twist”

Lorelai and Luke
For girls who never give up on their dreams even though their dreams are idiotic.


Best Episode: Season 4, Episode 21, “Last Week Fights, This Week Tights”
To be honest, Luke and Lorelai were kind of a train wreck once they actually started dating. This episode perfectly captures one of those last moments before Hurricane Lorelai derailed their friendship.

Honorable Mentions:
Season 1, Episode 10, “Forgiveness and Stuff”
Season 4, Episode 14, “The Incredible Shrinking Lorelais”
Season 4, Episode 20, “Luke Can See Her Face”
Season 4, Episode 22, “Raincoats and Recipes”
Season 5, Episode 3, “Written in the Stars”
Season 5, Episode 15, “Jews and Chinese Food”
Season 5, Episode 22, “A House is Not A Home”
Season 7, Episode 22, “Bon Voyage”

Lorelai and Jason
For girls with daddy issues

“I’m going to go make out in the coat room. Don’t eat my chicken.”

Best Episode: Season 4, Episode 18, “Tick, Tick, Tick, Boom!”
OK, people, Jason’s father hired a PRIVATE INVESTIGATOR to tail his own son and it catalyzes the shit storm that ultimately ends Lorelai and Jason’s relationship.

Honorable Mentions:
Season 4, Episode 6, “An Affair to Remember”
Season 4, Episode 13, “Nag Hammadi Is Where They Found the Gnostic Gospels”
Season 4, Episode 19, “Afterboom”

Lorelai and Max
For girls who had elaborate fantasies about banging her high school English teacher on his desk

Man, talk about “Paradise Lost”

Best Episode: Season 1, Episode 11, “Paris is Burning”
Lorelai takes home a gold star for hooking up with a teacher on Parent’s Day at Chilton. A+, Ms. Gilmore.

Honorable Mentions:
Season 1, Episode 8, “Love and War and Snow”
Season 1, Episode 21, “Love, Daisies and Troubadours”
Season 2, Episode 1, “Sadie, Sadie”
Season 3, Episode 19, “Keg! Max!”

Sookie and Jackson
For normal human beings who just want to stay out of the drama.

Jackson for town selectman… of my heart

Best Episode: Season 1, Episode 12, “Double Date”
Thanks to Jackson’s bizarre cousin Rune, Sookie and Jackson have the most perfect, adorable, awkward first date in the history of TV.

Honorable Mentions:
Season 2, Episode 22, “I Can’t Get Started”
Season 5, Episode 21, “Blame Booze and Melville”

Special thanks to Alyssa Howard, Alison Decker, and Bridget Illing for their contributions to this round-up.