Gabbing Gilmore: A Gilmore Girls Deep Dive

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)

Gabbing Gilmore: A Gilmore Girls Deep Dive

Show Notes

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.

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More from Gabbing Gilmore: A Gilmore Girls Deep Dive

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Of all the Stars Hollow town festivals, the Bid on a Basket event is not discussed enough! But arguably, it had the biggest impact on our favorite Gilmore Girls women. Today, we chat about the blowback of this seemingly cute and harmless town tradition. Lorelai, Rory, Sookie, and Lane’s lives all changed after Taylor began the auction! Let’s chat about how each of their storylines changed - for better or for worse.

Oct 14, 2026

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.

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Sep 23, 2026

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

Sep 9, 2026

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?

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