Gilmore Girlsis widely regarded as a great option for a seasonal re-watch in the fall and winter months, thanks to some particularly upbeat episodes. The show, which centers onthe ever-evolving lives of the titular Gilmore women against the quaint backdrop of small-town Connecticut, is not without its hard-learned lessons.Lorelai Gilmore (Lauren Graham) had her daughter Rory Gilmore(Alexis Bledel) when she was a teenager, and much of the show centers around them learning from one another and managing to both break and continue generational patterns.
For seasonal re-watchers, there are certainly some more festive episodes that break up the tension. From Rory’s college move-in day at Yale University to an unconventional Thanksgiving,Gilmore Girlsremains a classicfor its many heartwarming moments that bring the show’s characters together. WhileGilmore Girlshas several plot lines that are now viewed differentlyunder the microscope of contemporary criticism,its timeless quality lies in its ability to showcase life’s milestones.
10"Love And War And Snow"
Season 1, Episode 8
This episode marks the first snow-covered Stars Hollow appearance inGilmore Girls.Lorelai is known to have an affinity for snow throughout the show’s seven-season run, and giddily says “everything is magical when it snows.” This episode sees Rory snowed in at her grandparents, Emily (Kelly Bishop) and Richard’s (Edward Hermann) house in Hartford on a night that would’ve been a Friday night dinner (a tradition Lorelai agreed to in order for Emily and Richard to finance Rory’s Chilton tuition).There are many heartwarming moments, including when Rory introduces Emily to a frozen pizza.
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This givesLorelai a night in Stars Hollow to continue getting to know Max Medina,Rory’s teacher. The romantic evening is cut short when Rory’s friend Lane Kim (Keiko Agena) arrives seeking advice. Lorelai gives Lane an inspiring pep talk about the growing pains of being a teenager, all while Luke Danes (Scott Patterson) is battling Taylor Doosey’s literal Revolutionary War reenactment happening outside his diner. In typical Luke fashion,he ends up caving in and bringing hot chocolate to the freezing men outside.This is a great episode that establishes the nature of the relationships between many of the show’s characters.
9"The Lorelais' First Day at Yale"
Season 4, Episode 2
This episode marks another important milestone–Rory’s college move in. After dreaming of attendingHarvard her whole life, Rory instead decides on Yale, due to its proximity to Stars Hollow and her family’s legacy with the university. As Rory prepares to move in, Lorelai is eager to document the entire process. Lorelai is emotional surrounding this major step in Rory’s life, as she never got to attend college while raising Rory, though viewers see her earn a business degree later in the show.
The show is also a pivotal teaser thatLuke and Lorelai’s long-standing friendship will soon turn romantic.As usual, Rory’s father, Christopher Hayden (David Sutcliffe), is absent from moving in, but Luke is there to offer a helping hand. There is a particularly humorous predicament about a mattress, and another familiar face appears – Paris Gellar (Liza Weil), Rory’s rival turned friend from Chilton, is her new roommate.
8"Last Week Fights, This Week Tights"
Season 4, Episode 21
This hilariously touching episode is one for the history books ofGilmore Girls.Luke’s sister, Liz Danes (Kathleen Wilhoite), gets married to the comical TJ (Michael DeLuise) in a renaissance fair-inspired ceremony. The whimsical pair met while Liz was selling jewelry at the Renaissance Fair. Liz' son, Jess Mariano (Milo Ventimiglia), works on coming to terms with his new stepfather, which leads to him doing inner work with the help of a guided self-help book. Jess returns for the wedding after spending time living with his estranged father in California. His time thereevidently led to some much-needed personal growth.
Jess is working through his past treatment of Roryand even paying Luke back all the money he once took from him in high school. The wedding stirs up feelings in Luke and Jess to finally go after what they want.Luke is finally direct in his feelings for Lorelai, and the pair spend a romantic evening together that culminates in him asking her out on a real date. Jess attempts to ask Rory to go to New York with him for the summer, but she turns him down, beginning down a dangerous path with her ex-boyfriend Dean Forrester (Jared Padalecki).
7“Those Are Strings, Pinocchio”
Season 3, Episode 22
This episode marks Rory’s high school graduation from Chilton. In a touching moment during her valedictorian speech, Rory refers to Lorelai as her “ultimate inspiration.“Lorelai’s best friend Sookie St. James (Melissa McCarthy), her boyfriend Jackson Belleville (Jackson Douglas), Luke, Emily, and Richard are all in attendance. Rory’s speech reminds viewers of the thesis of the show –that oftentimes, it really does take a village. The episode is full of sentimental and reflective moments as Rory prepares to embark on her Ivy League education.
Rory’s speech reminds viewers of the thesis of the show – that oftentimes, it really does take a village.
Lorelai feels proud that her daughter is able to pursue her dreams in a way that she herself was unable to at her age. While the episode is an uplifting one overall, it also includes a sad moment towards the end. Rory has been receiving silent phone calls from unknown numbers, and begins to question if they’re from Jess in California. Rory finally picks up, and in her final message, says “I think I may have loved you, but I just need to let it go.“Jess is then seen on the other linefrom Venice Beach, marking the end of their relationship.
6"Kiss And Tell”
Season 1, Episode 7
This episode offers a wholesome look at Rory’s first love with Dean.Rory meets Dean as his family moves to Stars Hollow from Chicago, on her last day at Stars Hollow High before she transfers to Chilton. Despite going to different schools, Rory still runs into Dean all over town, since he works at Doose’s Market bagging groceries after school.Dean becomes Rory’s first kiss in this episode, when they exchange witty banter at the grocery store.
The kiss leaves Rory so speechless that all she can muster is a “thank you” before running out of the store with a box of corn starch. The rest of the episodeshowcases the awkwardness of a first relationship, and offers an endearing look at love in its simplest form. Rory and Dean begin dating, and the small town community that raised Rory is all invested. The episode later serves as a reminder that oftentimes, first love is not final love, as Rory and Dean are not well-matched anymore as adults. Nonetheless,their relationship was still an important one.
5"The Festival of Living Art”
Season 4, Episode 7
ThisGilmore Girlsepisode is a great example of Stars Hollow’s many unique town events. The charity event features townspeople recreating famous works of art live on stage. Kirk takes the role of Jesus in “The Last Supper,” Rory transforms into the “Portrait of a Young Girl Named Antea,” and Lorelai steps into Renoir’s “Dance at Bougival.” The visually striking event is a testament to the show’s whimsical eccentricity, including one of Kirk’s (Sean Gunn) many odd jobs.
This episode ofGilmore Girlswon the WB production its only Emmy Award, for Outstanding Makeup. This episode dialed up the cinematic quality of the show, and feels incredibly immersive to the viewer. Outside its testament to the world building of Stars Hollow,this episode is also a testament to Lorelai’s creativity, and the lengths the community goes to support one another.This moment offers a break from the melodrama ofGilmore Girlsseason 4.
4"The Bracebridge Dinner”
Season 2, Episode 10
This cozy holiday episode depicts Lorelai and Sookie planning and executing an elegant eventat their first workplace in the show, the Independence Inn. Lorelai is the Inn’s manager and Sookie is the in-house chef. The Bracebridge Dinner invites theGilmores' friends and family for a Christmas dinnercomplete with sleigh rides around the snow covered down, and the scenic views are perfect for a re-watch. The dinner is an example of Lorelai and Sookie’s many great personal and professional collaborations throughoutGilmore Girls.
This episode dials up the growing rivalry between Jess and Deanas they vie for Rory’s affections. Meanwhile, Rory is happy in her relationship with Dean while also finding herself with complex feelings about her friendship with Jess. The sleigh ride gossip is abundant, and Lorelai and Luke’s slow burn continues.
3"Raincoats and Recipes”
Season 4, Episode 22
This highly-ratedGilmore Girlsepisodesees Lorelai and Sookie realizing their dream of opening their own business together.They decide to test out the Dragonfly Inn with friends and familyfirst for a weekend, to work out any issues before it is open to the public. This episode follows Liz Danes' wedding to TJ, and continues Luke and Lorelai’s romance after a lengthy slow burn. In “Raincoats and Recipes”, Luke and Lorelai share their first kiss in the show, and officially begin their relationship.
With the happy news of the inn opening and Lorelai’s new relationship with Luke comes some serious drama, in typicalGilmore Girlsfashion. In the same episode, Emily and Richard admit to Lorelai that they have separated. At the same time, Rory loses her virginity toDean, who is now married to Lindsay Shaw (Arielle Kebbel). When Lorelai finds out, she is highly critical of Rory, and strongly disproves his infidelity.
2"Girls in Bikinis, Boys Doin' the Twist"
Season 4, Episode 17
ThisGilmore Girlsepisode has the ever-academic Paris and Rorytaking a walk on the wild side. The pair join their old Chilton friends Madeline (Shelly Cole) and Louise (Teal Redmann) for a spring break getaway to Florida. As the two rigid students attempt to unwind, hijinks ensue when Rory attempts to flirt with a random stranger to attempt to move on from Dean. The Shins cameo in this episode, and perform live in a club that the group of girls goes to. As usual, Paris has many quotable moments.
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This episode is mostly all good fun, but has its dose of conflict. Luke, who married Nicole Leahy (Tricia O’Kelly) on a whim earlier this season, was struggling to make the relationship work in the real world. When he discovers she has gone back to an ex-boyfriend instead of working on their relationship (all through finding a mysterious pair of socks in his apartment),he damages the man’s car with a baseball back. In the end, Lorelai literally bails him out of jail.
1“A Deep-Fried Korean Thanksgiving”
Season 3, Episode 9
This Thanksgiving episode is one of the many iconic seasonal spreads thatGilmore Girlshas to offer. The episode depicts how the townspeople of Stars Hollow each celebrate the holiday, and blend their traditions together. Lorelai and Rory drop by Luke’s Diner for his Thanksgiving special, while Sookie enjoys Jackson’s family tradition of an entirely deep-fried meal. Meanwhile, Lane’s family has a traditional Korean celebration, and her boyfriend,Dave Rygalski (Adam Brody)attempts to woo her religious mother by playing Christian hymns on his guitar.
The episode also features a hilariously drunk Sookie, and some sassy French dinner guests at Emily and Richard’s house. The moment is truly an amalgamation of the heart and soul ofGilmore Girlsthat continues to earn the show such devoted fans. The witty dialogue, pop culture references, and whimsical small town feel are the pinnacle of this holiday special.
Gilmore Girls
Cast
In the fictional town of Star’s Hollow, single mother Lorelai Gilmore raises her high-achieving teenage daughter Rory. Mother and daughter rely on each other throughout their own life changes, romantic entanglements, and friendships.
