‘Gilmore Girls,’ Season Two: 4 Must-See, Absolutely Essential Episodes

After Lorelai breaks off her engagement to Max (without, ya know, telling him) the Gilmore girls’ skip town in favor of a road trip. The duo lands at the Cheshire Cat, a bed and breakfast full of truly obnoxious tourists whom they try to —unsuccessfully — evade. When Lorelai realizes that they landed within driving distance of Harvard, the pair take off and explore the hallowed halls. Meanwhile, word spreads around town about the broken engagement and a certain diner owner is very pleased.

The episode is another demonstration of the unclear relationship dynamics that plague the Gilmore women. Lorelai aimlessly runs away from her problems like a teenager while Rory attempts to steer the spontaneous adventure with the help of a map. While Lorelai won’t talk about her emotions surrounding the end of her engagement, Rory encourages Lorelai not to bury them. When touring Harvard, it’s Lorelai who jokes about not wanting Rory to move away, not Rory who is scared about moving. Despite their sometimes unhealthy relationship, the love the two women share cannot be questioned.

Back in Stars Hollow, Luke’s reaction to the end of Lorelai’s engagement continues to plant wonderful seeds of possibility between the gruff diner owner and quirky inn manager. That relationship ends up being one of the main cornerstones in the show — even though the audience had to wait until season four for it to come to fruition — and this is one of the first moments where viewers dared to dream.

[Watch “The Road Trip to Harvard” on Netflix]

Jess Mariano, Luke’s somewhat troubled nephew, makes his Stars Hollow debut with the apt “This is Hell” playing in the background. Jess’s introduction does not go smoothly; he manages to anger Lorelai, frustrate Luke to the point that he pushes Jess in a lake, steal money intended for a fundraiser, and abduct one of Babette’s garden gnomes (no worries, Pierpont was returned unharmed). Meanwhile Rory — the only person Jess does like — is forced to interview her almost stepfather Max thanks to Paris.

This episode is the denotative definition of essential. Not only does it introduce the best boyfriend Rory ever has (#TeamJess), but it also sets up the inevitable downfall of the Dean and Rory love story — at least until their ill-fated season four tryst. There’s an instant attraction between Jess and Rory, which can be felt the moment he steps into her room and tries to climb out of the window. When Rory learns that Jess stole her book — because he wanted to leave notes in the margins for her! — she questions him, “I thought you didn’t read much?” He responds in an ultra-Jess way and with his soon-to-be signature smirk, “What is much?”

Elsewhere, Lorelai is kind of an adult for once. She gives Luke advice on Jess and is mature about Rory’s forced interview with Max. This marks one of the first times when Luke needs Lorelai for something, a major switch in the dynamics of their relationship. It’s Lorelai who needed Luke when her dad had a heart attack, when they were out of ice at Rory’s birthday party, and when Rory’s school assigned bird escapes in the house. This time Luke needs Lorelai and she delivers.

[Watch “Nick and Nora/Sid and Nancy” on Netflix]

Lorelai’s graduation from community college comes and, against Lorelai’s wishes, Rory invites Richard and Emily to the ceremony. Despite their somewhat embarrassing stunts before and during the ceremony, it’s one of the only times that their pride for Lorelai is evident. Rory, the only person Lorelai wanted at the ceremony, cuts school to visit Jess — who moved back to New York after crashing Rory’s car, which resulted in Rory having to get a cast — ends up missing the commencement thanks to a local bus and a gross guy with a spit can.

When Lorelai switches her tassel over on the badly lit community college stage the camera flashes to Richard and Emily wearing similar expressions of delight and regret; delight that she finally did it and regret that it came so much later in life than they had planned. Despite their uppity attitude, the elder Gilmores cared enough about Lorelai’s graduation to attend the ceremony, have it filmed, and take a family picture. That’s more than can be said for Rory.

Missing Jess, though technically still with Dean, Rory cuts school, heads for Manhattan, and manages to stumble upon Jess in the middle of Washington Square Park. The duo get hot dogs, take the subway, and go to a kickass record store. It’s an easy reminder that Jess and Rory have a lot in common, while Rory’s similarities to Dean seem to diminish more and more each episode.

Rory ends up missing the ceremony because her bus got delayed and it’s easily one of the worst things she’s done in the series thus far, equal perhaps to staying out all night with Dean the night of her dance. Rory apologizes profusely to her mother — promising Lorelai complete power over the remote and take-out choices for the near future — and Lorelai accepts despite her disappointment in Rory. Their relational roles are what they should be in this episode — Lorelai is the adult who completed college, (sort of) bonded with her parents, and forgave Rory; Rory is the teenager who skipped school, hopped on a bus, and visited a strange city to see a guy who wasn’t her guy. It’s an intriguing episode about handling mistakes and forgetting regret in the name of love.

[Watch “Lorelai’s Graduation Day” on Netflix]

Season two comes to a close with a real bummer of an episode. Just when Chris and Lorelai are finally ready to give their relationship a chance, Sherry announces that she’s pregnant with Chris’s baby. Meanwhile, Jess returns to Stars Hollow and asks Luke if he can move back. After Luke agrees, Jess seeks Rory out at Sookie’s wedding to Jackson and the two share their first kiss. The episode ends with mother and daughter reeling about the men in their lives.

As much as I’m firmly in the Team Luke camp, the end of Chris and Lor’s relationship — until season six — is still upsetting. This is true mostly because their parting is due to a mistake Chris has made before. I mean seriously, did Chris miss the sex ed day in high school or learn anything from getting Lorelai pregnant at sixteen? Condoms are a thing you should use, Chris!

As clear as it is that Rory should absolutely not have cheated on Dean, the Jess thing was basically inevitable and something that viewers should have been able to enjoy. But that should be exciting moment that fans had been waiting for all season was undercut by what a “mistake” it was for her to cheat on Dean.

At the end of the day, Lorelai knows that it’s over with Chris and Rory knows that she wants to be with Jess. They both have super mature ways of dealing with their boy troubles of course; Lorelai starts season three by avoiding Chris at all costs while Rory runs away to leadership camp in D.C. — following her election as vice president of the student body at Chilton — where she doesn’t contact Jess and is flighty with Dean.

Despite the upsetting storylines in the episode, Sookie’s wedding is beautiful, Lorelai has a rare nice moment with Emily, and, in the moment, Jess and Rory’s first kiss is pretty adorable. Season three will see the ladies in new relationships, focused on Rory’s upcoming move to college, and attending all of the quirky town events that you can handle.

[Watch “I Can’t Get Started” on Netflix]