Gilmore Girls is widely considered a great option for seasonal rewatching in the fall and winter months thanks to some particularly upbeat episodes. The show, centered on the ever-evolving lives of Gilmore's titular women in the picturesque setting of small-town ConnecticutIt is not without lessons learned with difficulty. Lorelai Gilmore (Lauren Graham) had her daughter Rory Gilmore (Alexis Bledel) when she was a teenager, and much of the show revolves around them learning from each other and managing to break and continue generational patterns.
For seasonal watchers, there are certainly some more festive episodes that break the tension. From the day Rory moves into college at Yale University to an unconventional Thanksgiving, Gilmore Girls remains a classic for its many emotional moments that bring the series' characters together. While Gilmore Girls has several plots that are now viewed differently under 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 appearance in Stars Hollow in Gilmore Girls. Lorelai is known for having an affinity for snow throughout the show's seven seasons, and giddily says:everything is magical when it snows." This episode finds Rory stuck in the snow at her grandparents', Emily (Kelly Bishop) and Richard's (Edward Hermann) house in Hartford on a night that would have been a Friday night dinner (a tradition that Lorelai agreed to so that Emily and Richard to finance Rory's tuition at Chilton). There are many touching moments, including when Rory presents Emily with a frozen pizza.
This gives Lorelai a night in Stars Hollow to continue getting to know Max Medina, Rory's teacher. The romantic night is interrupted when Lane Kim (Keiko Agena), Rory's friend, arrives looking for advice. Lorelai gives Lane an inspirational speech about the growing pains of being a teenager, while Luke Danes (Scott Patterson) is struggling with Taylor Doosey's literal Revolutionary War reenactment happening outside his restaurant. In typical Lucas fashion, he ends up giving in and bringing hot chocolate to the frozen men outside. This is a great episode that establishes the nature of the relationships between many of the series' characters.
9
"The Lorelais' First Day at Yale"
Season 4, Episode 2
This episode marks another important milestone–Rory’s move to college. After dreaming of attending Harvard all her life, Rory decides to go to Yale, due to its proximity to Stars Hollow and her family's legacy with the university. As Rory prepares to move, Lorelai is eager to document the entire process. Lorelai is thrilled about this big step in Rory's life, as she was never able to attend college while raising Rory, although viewers see her earning a business degree later in the show.
The show is also a key teaser that Luke and Lorelai's longtime friendship will soon turn romantic. As always, Rory's father, Christopher Hayden (David Sutcliffe), is absent from the move, but Luke is there to offer help. There's a particularly funny situation regarding a mattress, and another familiar face appears – Paris Gellar (Liza Weil), Rory's rival turned Chilton friend, is her new roommate.
8
"Last week's fight, this week's tights"
Season 4, Episode 21
This hilarious and heartwarming episode is one for the history books of Gilmore Girls. Luke's sister, Liz Danes (Kathleen Wilhoite), marries comic TJ (Michael DeLuise) in a ceremony inspired by a Renaissance fair. The eccentric pair met while Liz was selling jewelry at the Renaissance Fair. Liz's son, Jess Mariano (Milo Ventimiglia), works to come to terms with his new stepfather, which leads him to do some inner work with the help of a guided self-help book. Jess returns to her wedding after spending time living with her estranged father in California. Your time there evidently led to some much-needed personal growth.
Jess is resolving her treatment of Rory and even giving Luke back all the money he took from him in high school. The wedding awakens feelings in Luke and Jess of finally going after what they want. Luke is finally upfront about his feelings for Lorelaiand the two spend a romantic night together that culminates in him asking her out on a real date. Jess tries to ask Rory to spend the summer with him in New York, but she refuses, starting a dangerous path with her ex-boyfriend Dean Forrester (Jared Padalecki).
7
“These are ropes, Pinocchio”
Season 3, Episode 22
This episode marks Rory's graduation from high school in Chilton. In a touching moment during her valedictorian speech, Rory refers to Lorelai as her “final inspiration." Lorelai's best friend Sookie St. James (Melissa McCarthy), her boyfriend Jackson Belleville (Jackson Douglas), Luke, Emily and Richard are present. Rory's speech reminds viewers of the show's thesis – that it often takes a village. The episode is filled with sentimental and reflective moments as Rory prepares to embark on her Ivy League studies.
Rory's speech reminds viewers of the show's thesis – that often it really does take a village.
Lorelai is proud that her daughter is able to pursue her dreams in a way that she herself could not at her age. While the episode is uplifting overall, it also includes a sad moment at the end. Rory has been receiving silent phone calls from unknown numbers and begins to wonder if they are from Jess in California. Rory finally answers and in his final message he says: "I think I may have loved you, but I just need to let it go." Jess is then seen on the other line of Venice Beach, marking the end of the relationship.
6
"Kiss and tell"
Season 1, Episode 7
This episode offers a complete look at Rory's first love with Dean. Rory meets Dean when his family moves from Chicago to Stars Hollow, on his last day at Stars Hollow High before transferring to Chilton. Despite attending different schools, Rory still runs into Dean all over town, as he works at Doose's Market bagging groceries after school. Dean becomes Rory's first kiss in this episodewhen they exchange witty banter in the supermarket.
The kiss leaves Rory so speechless that all she can manage is a "thanks" before running out of the store with a box of cornstarch. The rest of the episode shows the strangeness of a first relationshipand offers a captivating look at love in its simplest form. Rory and Dean start dating, and the small town community that raised Rory is all invested. The episode later serves as a reminder that often first love is not final love, as Rory and Dean no longer match as adults. Despite that, their relationship was still important.
5
"The Living Art Festival"
Season 4, Episode 7
That Gilmore Girls The episode is a great example of the many events unique to the town of Stars Hollow. The charity event features city residents recreating famous works of art live on stage. Kirk takes on the role of Jesus in “The Last Supper,” Rory takes on the role of “Portrait of a Young Woman Called Antea,” and Lorelai steps into Renoir’s “Dance at Bougival.” The visually stunning event is a testament to the show's whimsical eccentricity, including one of Kirk's (Sean Gunn) many odd jobs.
This episode of Gilmore Girls won the WB production its only Emmy award, for Best Makeup. This episode increased the cinematic quality of the show and feels incredibly engaging for the viewer. Outside of your testimony of the world-building of Stars Hollow, This episode is also a testament to Lorelai's creativity and how far the community goes to support each other. This moment offers a break from the melodrama of Gilmore Girls season 4.
4
"The Bracebridge Dinner"
Season 2, Episode 10
This cozy holiday episode finds Lorelai and Sookie planning and executing an elegant event at her first place of work on the show, the Independence Inn. Lorelai is the inn manager and Sookie is the chef of the house. The Bracebridge Dinner invites the Gilmores' friends and family to a Christmas dinner complete with snow-covered sleigh rides, and the panoramic views are perfect for rewatching. The dinner is an example of Lorelai and Sookie's many great personal and professional collaborations throughout the year. Gilmore Girls.
This episode shows the growing rivalry between Jess and Dean as they compete for Rory's affections. Meanwhile, Rory is happy in her relationship with Dean while also grappling with complex feelings about her friendship with Jess. Gossip about sleigh rides abounds, and Lorelai and Luke's slow burn continues.
3
"Raincoats and recipes"
Season 4, Episode 22
This highly rated Gilmore Girls The episode shows Lorelai and Sookie realizing their dream of opening their own business together. They decide to test the Dragonfly Inn with friends and family first for a weekend, to iron out any issues before opening to the public. This episode follows Liz Danes' wedding to TJ and continues Luke and Lorelai's romance after a long, slow burn. In "Raincoats and Recipes", Luke and Lorelai kiss for the first time on the show and officially begin their relationship.
With the happy news of the inn's opening and Lorelai's new relationship with Luke, serious drama arises.in typical Gilmore Girls fashion. In the same episode, Emily and Richard admit to Lorelai that they broke up. At the same time, Rory loses her virginity to Dean, who is now married to Lindsay Shaw (Arielle Kebbel). When Lorelai finds out, she strongly criticizes Rory and vehemently refutes his infidelity.
2
"Girls in bikinis, boys doing twists"
Season 4, Episode 17
That Gilmore Girls episode has the always academic Paris and Rory taking a walk on the wild side. The pair join their old Chilton friends Madeline (Shelly Cole) and Louise (Teal Redmann) for a springtime getaway in Florida. While the two strict students try to relax, shenanigans ensue when Rory tries to flirt with a random stranger in an attempt to move on with Dean. The Shins participate in this episode, and perform live at a nightclub that the group of girls frequents. As always, Paris has many quotable moments.
This episode is mostly fun, but it has its fair share 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 finds out that she went back to an ex-boyfriend instead of working on their relationship (all because of finding a mysterious pair of socks in her apartment), he damages the man's car with a baseball to the back. In the end, Lorelai literally bails him out of jail.
1
“A Stir-Fried Korean Thanksgiving”
Season 3, Episode 9
This Thanksgiving episode is one of many iconic seasonal shows that Gilmore Girls has to offer. The episode shows how the townspeople of Stars Hollow celebrate the holiday and mix up their traditions. Lorelai and Rory stop by Luke's Diner for their Thanksgiving special, while Sookie enjoys the Jackson family tradition of an all-fried meal. Meanwhile, Lane's family has a traditional Korean celebration, and her boyfriend, Dave Rygalski (Adam Brody), tries to woo his religious mother by playing Christian hymns on his guitar.
The episode also features a hilariously drunk Sookie and some sassy French guests for dinner at Emily and Richard's house. The moment is truly an amalgamation of the heart and soul of Gilmore Girls this continues to win the show such devoted fans. The witty dialogue, pop culture references, and whimsical small-town atmosphere are the height of this holiday special.