5. “Friday Night’s Alright for Fighting” (Season 6, Episode 13)
Season 6 takes us on a bumpy ride, as Rory leaves Yale in the wake of her disastrous decision to steal a yacht with Logan, moves into her grandparents’ pool house, and joins the Daughters of the American Revolution. But midway through the season, Jess surprises Rory with a visit and reams her out for all her life decisions — particularly the choice to quit college. In episode nine, “The Prodigal Daughter Returns,” Rory and Lorelai finally reunite, as Rory leaves the pool house and goes back to Yale.
So, four episodes later, Rory and Lorelai head to Hartford for their ritual Friday night dinner — their first following the news that Rory’s dad Christopher is going to pay for her tuition at Yale, which releases Rory from her obligation to attend the weekly meal.
The episode builds to this final doozy of a scene, a five-minute-long argument between the four Gilmores that breaks from the show’s house direction in hilarious fashion. Lorelai is simmering over Luke’s terrible decision to keep his long-lost daughter, April, out of her life, upending their engagement plans, and Rory has just swept in to rescue the staff of the Yale Daily News after Paris, the editor-in-chief, has a tyrannical breakdown and builds a bunker in the newsroom.
In the aftermath of all that, the Gilmore girls dutifully show up for dinner at Emily and Richard’s house, where things are a bit off — Emily, for one, is out on the patio, painting moonscapes. But when the group sits down for dinner, the gloves come off, and a roving camera sets the tone for this epic, expertly edited sequence. Nothing is off-limits: Lorelai’s refusal to marry Christopher when she got pregnant as a teenager; Rory’s moving in, and then out, of her grandparents’ house; the time Emily tried to time-share a plane. At one point, the gang pauses to marvel at the passionfruit sorbet. The scenes cut quickly into each other, emphasizing the pile of issues that this WASP-y family has left untouched for so long. In the end, Rory and Lorelai emerge from the house in emotional tatters. “I think we’ve officially reinstated Friday night dinner,” Lorelai says.
Best Line: Lorelai [re: Paul Anka, the dog]: “He’s totally fine having his personal freedom slowly stripped away, as long as he’s completely unaware that it’s happening. Just like a true American.”
4. “The Big One” (Season 3, Episode 16)
The title of this episode technically refers to the size of the envelope that confirms Rory’s gotten into Harvard. But it could easily apply to the big event in Paris’s life that she reveals to Rory in this episode: She has sex for the first time, with her college boyfriend, Jamie. I’m a sucker for any Gilmore Girls episode that heavily features Paris, a cynical ballast to Rory’s apple-cheeked sincerity. (“Maybe someday I’ll stumble into a Disney movie and suddenly be transported into your body, and after living there awhile, I’ll finally realize the beauty of myself,” Paris spits at Rory in Season 2’s “Like Mother, Like Daughter.”)
As Rory and Lorelai wait on the results of Rory’s college applications, Rory and Paris team up for a speech at Chilton, which will be broadcast live on C-SPAN — a detail only Rory and Paris could get excited about. “The Big One” highlights the relationship between these two overachievers, who begin as enemies but grow closer as they motivate each other to succeed. Headmaster Charleston decides their entries for the speech competition were both so good, they should combine them into one speech and present it together.
When Paris shows up at Rory’s house to practice, she drops the bomb that she lost her virginity. Rory confesses that she never had sex with Dean or Jess (while Lorelai, who’s just returned home with pizza, listens in); the conversation marks a turning point in their friendship, which will follow them to Yale in Season 4 when Paris arranges for them to live in the same dorm room.
But really, the best part about “The Big One” is Paris’s live-on-C-SPAN meltdown. She shows up at the last minute, looking disheveled in a baggy sweater, her hair in a messy ponytail, and informs the crowd gathered at the prestigious prep school that she didn’t get into Harvard. “I had sex, but I didn’t get into Harvard. If you asked me last year which of those two would be more likely to happen, it would not have been not getting into Harvard!” Rory eventually drags her offstage, and she and Lorelai come home to find not one, but four of those “big ones” in their mailbox.
Best Line: Lorelai [re: C-SPAN]: “It’s like watching the Men’s Wearhouse security camera.”
3. “Raincoats and Recipes” (Season 4, Episode 22)
This is the episode where Rory loses her virginity, and Lorelai and Luke lose their mouth-virginity (eww, sorry). The Season 4 finale, “Raincoats and Recipes” depicts Sookie and Lorelai’s test-run for their newly renovated Dragonfly Inn. Like Season 2’s “The Bracebridge Dinner,” this episode gets points for gathering all the eccentric residents of Stars Hollow together at once. (This is also the episode where we’re introduced to Kirk’s “night terrors.”)
The episode comes at the end of a season that sees Rory struggling to fit in for the first time since she enrolled at Chilton in Season 1. Whether she’s trying to find the perfect study spot at Yale; hiding in her room with Paris and a VHS of Joseph Campbell and the Power of Myth during spring break; or bumbling through an awkward first date, the Rory of Season 4 is out of her element. So it’s no surprise that she winds up losing her virginity to her reliable high-school boyfriend Dean — the two flirt all season long, despite his recent marriage to Lindsay.
Lorelai, too, ends up with Luke after spending the season on a new endeavor — opening her very own inn with Sookie, after working at the Independence Inn since Rory was a baby. But their kiss, on the steps of the Dragonfly Inn as Kirk runs screaming into the night, is tainted when Lorelai returns home to get some CDs and walks in on the aftermath of Rory and Dean’s first time. The episode ends with the biggest fight we’ve seen between mother and daughter, as Lorelai reminds Rory that “her Dean” is married, and Rory yells at her mother “for ruining this for me.”
Best Line(s): Lorelai: “What, I’m just saying, I’m surprised that Luke can waltz.” Rory: “That sounded more like, ‘I’m surprised I still have my clothes on.'”
2. “They Shoot Gilmores, Don’t They?” (Season 3, Episode 7)
It’s the one with the 24-hour, ’40s-themed dance marathon! A.k.a., the one where Dean breaks up with Rory because she’s so obviously into Jess. (You guys, I could do this all day.) Like three out of five episodes on this list, “They Shoot Gilmores, Don’t They?” gathers the whole nutty Stars Hollow ensemble in one place, at the high school gymnasium, where the annual Stars Hollow Dance Marathon rages on.
The marathon itself is the best of Gilmore Girls’ weird Stars Hollow traditions (the Festival of Living Art is a close second; pay no attention to the fact that none of these events is ever mentioned outside the episodes in which they’re introduced). The rules state that all dancers must have a partner, so of course, Lorelai and Rory pair up with each other, each dressed in their 1940s finest.
Lorelai and Luke share a romantic moment while waiting for the glue to dry on her vintage heels, which he helps her fix. But the real drama occurs when Jess shows up with his girlfriend, Shane, just to piss off Dean. And piss off Dean he does. Our floppy-haired prince gets so upset at Jess and Rory’s mutual ogling that he dumps Rory right there on the dance floor — which causes her and Lorelai to lose the competition to Kirk, who parades around the gym to the Rocky theme song with his trophy held high.
Best Line(s): Rory: “I can’t even open my eyes.” Lorelai: “That’s okay, there’s nothing to see. Kirk’s in a Speedo, Taylor’s in a skirt, Al’s in assless chaps.” Rory: “Oh my God, stop. I’m never gonna be able to close my eyes again.”
1. “I Can’t Get Started” (Season 2, Episode 22)
I can’t lie: Jess and Rory’s first kiss did not exactly hurt this episode’s chances of landing at the top of my list. But in many other ways, this episode, the second season finale (Gilmore Girls really knows how to stick a landing), reaches Peak Gilmore.
I’ve always been a firm believer in the supremacy of the third season of Gilmore Girls: It’s got all the good Rory and Jess drama, Emily and Richard are in fine form, Rory and Paris start to get friendlier, and with Rory finishing her final year at Chilton, the whole season carries the weight of her college applications and the tension of where she — and the subsequent season — will go.
“I Can’t Get Started” sets the tone and agenda for the third season, and it also features the lovely Sookie St. James’s wedding to Jackson-the-vegetable-man, the most appropriate union of two characters on this show. The wedding also means the whole town is gathered in one place, with everyone’s charming neuroses on display at once. Even Richard and Emily show up — and Emily, of course, notices that Christopher is there, too, fresh off a hot night with Lorelai at the Independence Inn.
But, alas, it’s not in the cards for these two (or, at least, it never should have been — the notoriously Amy-Sherman-Palladino-less seventh season resurrected their courtship and had them elope). Just before Lorelai is about to walk down the aisle with her fellow bridesmaid Rory — in custom-made dresses that Lorelai has sewn — Christopher breaks the news that his girlfriend, Sherry, is pregnant. And just before Rory walks down the aisle, she spies Jess, who recently left town to live with his mom in New York — and has just returned to move back in with Luke. Although she’s still with Dean, Rory breaks character and impulsively kisses him.
“I Can’t Get Started” nods to so many of the show’s ongoing dramas: The turbulent dynamic between Lorelai and Emily, who desperately wants her daughter to end up with Rory’s father; the undeniable chemistry between Lorelai and Christopher that could never quite form a bridge to a real relationship; the Rory-Jess-Dean love triangle.
Most of all, the episode exposes the cracks in Rory’s good-girl image that begin with her attraction to Jess and culminate with her boat-stealing stunt with Logan in Season 5, which drives a long-lasting wedge between her and Lorelai when Rory chooses to leave Yale and move in with her grandparents. The tension that leads to that infamous separation, which lasts for the first half of Season 6, begins with that first kiss between Rory and Jess, but it’s not really about Jess; it’s about Rory growing up and testing new waters, and the inevitable, painful moment when she slips out of Lorelai’s grasp, makes mistakes, and becomes her own person.
Best Line: Lorelai: “Oy, with the poodles already!”