Welcome back, Gilmore friends! ☕️ Today, Chemda and Carrie are breaking down Season 2, Episode 14, "It Should Have Been Lorelai" and let's just say, the title isn’t the only thing giving us major wistful vibes.

In this episode, Christopher breezes back into Stars Hollow, but he didn't come alone. Enter Sherry: the hyper-organized, boundary-crossing new girlfriend who is determined to bond with Rory while making it awkwardly clear that she and Lorelai don't need to be besties. From cringing at Sherry’s kitchen confrontation to unpacking Christopher’s peak entitlement (seriously, where is the 16 years of child support?!), we have thoughts.

Plus, we dive into Lane’s high-stakes, top-secret Belle and Sebastian CD heist involving a sweatsuit-clad Michel, Paris completely terrifying poor Brad at the Chilton debate, and Emily flipping out over the life Lorelai "missed out on." Carrie also shares a deeply personal, tear-jerking story about her own parents' post-divorce vacation that you won't want to miss.

Are you Team Christopher has his life together because of a Volvo, or are you with us in thinking he's still a total weasel? Let us know your thoughts in the comments below!

Welcome back to Stars Hollow! In this episode of Gilmore Friends, Chemda (the 20-millionth-time watcher) and Carrie (the Gilmore "pure" first-timer) dive into the iconic Season 2, Episode 13: "A Tisket, A Tasket."

The town is buzzing with the annual basket auction, but the "tradition" isn't sitting well with everyone. We break down the high-stakes bidding war between Dean and Jess for Rory's basket, and why $90 felt like a fortune in 2002. Plus, we discuss Sookie and Jackson’s major relationship milestone (despite the "green condom hat"), Lane’s devastating phone call with Henry, and Lorelai’s attempt to stay "the cool mom" while Emily Gilmore lurks in the wings.

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Timestamps:

00:00 Intro: The 20-Millionth Time vs. The First Time

00:56 Alternative Titles & "Basket Case"

03:06 The Famous Basket Auction Breakdown

04:41 High School Jealousy & Trusting Your Partner

06:08 The Weird Voiceover Intro & Town Signs

07:10 The Uncomfortable Reality of "Human Auctions"

10:09 "Buck Tradition": Is Stars Hollow Sexist?

11:56 Miss Patty’s Wallet Photo & Catfishing Fears

14:08 Jess vs. Dean: The Grocery Store Showdown

16:31 Red Flag Alert: Is Jess Only Nice to Rory?

19:06 90s Nerd-dom and Ghostbusters Resumes

20:15 Jackson’s Tiptoeing & Sookie’s "Naivety"

21:56 Heartbreak for Lane: The Broken Payphone

26:14 Soy Tacos & The Pre-Whole Foods World

28:46 Lorelai’s Closet Story & The Tree Accident

30:45 The $90 Prank: Jess Bids on Rory

33:56 Basket Logistics: Why Couldn't Dean Just Join?

36:05 Kirk’s Backstory & The Edible Pretzel Basket

38:44 Lorelai Interrupts Luke’s Workday

41:10 Pop Tarts & Slim Jims: Luke Knows Her Order

43:28 Henry Chooses Another Prom Date

48:40 The "Switcheroo" Proposal & Green Hats

51:56 "This is Nice": Luke and Lorelai’s Picnic

56:11 Trusting Your Kid vs. Predator Warnings

1:01:41 Emily Gilmore Agrees: The Flop House Smell

1:11:03 Trivia: Bob’s Burgers & Scott Patterson’s Audition

1:15:02 Paul Newman & The 1958 Movie Connection

1:19:32 Gendered Bathrooms & The Gutter in Brooklyn

1:23:00 Predictions: Car Drama & Lane’s Prom

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In this episode of Gilmore Friends, Chemda and Carrie dive into Season 2, Episode 12, "Richard in Stars Hollow." The retirement honeymoon is officially over as Richard’s new "hobby" becomes micromanaging Emily’s every move, from counting her morning coffees to tagging along to her DAR meetings and symphony luncheons. We discuss the relatable (and slightly cringey) transition of having a partner suddenly home 24/7 and Lorelai's "spirited" reaction to having her father invade her Stars Hollow sanctuary.

Meanwhile, at Chilton, Paris is on a warpath to win the Oppenheimer Award, dragging Rory on a mission to uncover the "seedy underbelly" of Stars Hollow. We also take a nostalgic trip back to the era of VHS vs. DVD at the video store, marvel at Kirk’s ever-growing resume, and debate the mysterious "Tabatha" reference that had us scrolling through Reddit for answers. Plus, we break down Dean's big car reveal, Richard's interference, and that surprising Yale legacy drop.