Gabbing Gilmore: A Gilmore Girls Deep Dive
Gabbing Gilmore

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101. (October Bonus) Gilmore Girls, Virginity & the Rules for Teenage Girls: good girl regrets & does boys’ virginity even matter? (Part 2 of 2)
14.10.2026 | 3 Min.What happens when a good girl decides to “lose” her virginity? Can her first time be pleasant or does society force penalties, regrets and guilt onto her? Exhibit A: Rory Gilmore and Paris Geller.
Today we’re back to discuss the portrayal of virginity of some of our other favorite young adult and teen heroines of the ‘90s and 2000s, like Felicity Porter, Blair Waldorf, and characters on One Tree Hill, Dawson’s Creek, and of course, Gilmore Girls.
Television shows give us an important cultural framework for teens and sex. So, we have to ask - what’s the role of boys in all this? We explore whether characters like Dawson Leery and Lucas Scott grapple with the same pressures as teenage girls, and feelings of entitlement that boys are raised with.
It’s a serious topic, but we’re going to leave you with some positivity and hope for the future, but be sure to stay until the end.
This episode is Part 2 of 2.
Content warning: includes discussion of sexual assault and purity culture. Take good care of yourselves, friends.
✨ This is an excerpt of a bonus episode. To access the full episode, join our Patreon, where you’ll get extra bonus episodes every month.
Edited and produced by Jackie Procyk and Catherine Bailey.
Advertising Inquiries: https://redcircle.com/brands- Rory Gilmore’s relationship with Logan Huntzberger is a bumpy ride - especially during their casual dating stage. We answer: why did Rory choose casual dating? How did Lorelai handle it? Did Logan gaslight Rory because of his commitment-phobia?
We cover poker night, the Pulp Friction party, crying on the bathroom floor, and everything in between. Finally, we’ve got theories about why Logan finally agreed to be exclusive.
✨ If you want more chats about Gilmore Girls, get extra bonus episodes every month at patreon.com/gabbinggilmore
☕Get a free gift with some yummy “coffee coffee coffee!” at https://larryscoffee.com/gabbing
🍿Download “How to Throw a GG Watch Party - the Ultimate Guide!” completely free for your next Gilmore gathering
☕ Shop our merch at https://gabbing-gilmore.printify.me/
🔎Remember, this is not a spoiler-free podcast, so everything is on the table.
👋Wanna share your thoughts? Leave us a voice note here at speakpipe.com/gabbinggilmore
Advertising Inquiries: https://redcircle.com/brands - Today, Catherine and Jackie are guests on a really fun podcast called Gilmore the Merrier.
We are absolutely delighted to join host Bran, a longtime Gilmore Girls fan, along with his friends Dan and Chad, who are watching the show for the very first time. They’re going episode by episode, recapping and discussing everything as they go—and invited us to jump in for their Season 2 finale discussion of “Can’t Get Started.”
This is one of Gabbing Gilmore's favorite season finales, I mean... those last five minutes!?! There is SO much to talk about. We get into some hot takes, including the all-important question: How do we feel about Rory kissing Jess?!
We also talk about Sookie’s pre-wedding meltdown, and we dig into Christopher showing up when Rory gets her cast removed. What are his real motivations? Is this genuinely about Rory—or is something else going on?
So, grab a cup of coffee, settle in, and join us as we revisit Season 2, Episode 22, “Can’t Get Started” with our new friends over at Gilmore the Merrier!
✨ If you want more chats about Gilmore Girls, get extra bonus episodes every month at patreon.com/gabbinggilmore
☕Get a free gift with some yummy “coffee coffee coffee!” at https://larryscoffee.com/gabbing
🍿Download “How to Throw a GG Watch Party - the Ultimate Guide!” completely free for your next Gilmore gathering
☕ Shop our merch at https://gabbing-gilmore.printify.me/
👋Wanna share your thoughts? Leave us a voice note here at speakpipe.com/gabbinggilmore
Advertising Inquiries: https://redcircle.com/brands 98. {September Bonus}The Virginity Obsession on Teen Dramas of the ‘90s and 2000s: Gilmore Girls, Harlots, Purity Culture, and Beyond (Part 1 of 2)
16.09.2026 | 5 Min.Today we’re diving into virginity stories on Gilmore Girls and other teen dramas. Rory, Paris, and Lane all experienced their first time on the show - all with different challenges and hangups.
So why is virginity such a frequent storyline for teenage girls, but rarely for boys? To answer that question, we started with Stars Hollow and continued to some of our other favorite YA and teen dramas of the ‘90s and 2000s, like My So-Called Life, 90210, Dawson’s Creek, Felicity, One Tree Hill, and Gossip Girl.
Along the way, we name the 3 most common tropes used to portray teenage girls and their sexuality, against the backdrop of Britney Spears, Jessica Simpson, and the rise of purity culture in mainstream culture.
This episode is Part 1 of 2.
Content warning: includes discussion of virginity testing, sexual assault, purity culture, and sexual health. Take good care of yourselves, friends.
✨ This is an excerpt of a bonus episode. To access the full episode, join our Patreon, where you’ll get extra bonus episodes every month.
Edited and produced by Jackie Procyk and Catherine Bailey.
Advertising Inquiries: https://redcircle.com/brands- Court is in session! The jury will now hear two arguments: were Emily and Richard Gilmore right about Rory dropping out of Yale? Or should they have gone with Lorelai’s plan?
Today, Jackie and Catherine will make the case for each party.
What could Lorelai have done better? When did Richard and Emily act too hastily? And finally, what do we wish someone would’ve told Rory? Today, we answer all those questions.
✨ If you want more chats about Gilmore Girls, get extra bonus episodes every month at patreon.com/gabbinggilmore
☕Get a free gift with some yummy “coffee coffee coffee!” at https://larryscoffee.com/gabbing
🍿Download “How to Throw a GG Watch Party - the Ultimate Guide!” completely free for your next Gilmore gathering
☕ Shop our merch at https://gabbing-gilmore.printify.me/
🔎Remember, this is not a spoiler-free podcast, so everything is on the table.
👋Wanna share your thoughts? Leave us a voice note here at speakpipe.com/gabbinggilmore
Advertising Inquiries: https://redcircle.com/brands
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Über Gabbing Gilmore: A Gilmore Girls Deep Dive
If Gilmore Girls is your “comfort food,” join sisters Jackie and Catherine in this deep dive discussion of all things Stars Hollow. Coming to you straight from Connecticut, the sisters’ deep love for Lorelai & Rory fuel their “gabbing” about themes like single motherhood, feminism, friendship, parenting, and yes… of course, Rory’s boyfriends. So grab some red vines and coffee, and join these two GG pros for a walk through town square. Copperboom! P.S. every juicy morsel is on the table. So... not spoiler-free.
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