Long Winded with Gabby Windey

Given her vast array of expertise, Gabby Windey takes her guests on a deep dive into the topics today’s audiences care about: dating (duh), sexuality (hell yes), health & mental health (ugh so important) plus a healthy dose of pop culture shit talk. Each episode, Gabby will be interviewing guests with the ultimate goal to break down walls and get beyond the typical interview questions— “So tell us about yourself” doesn’t actually tell us anything about who the person really is- does it?! Instead, she skips the surface and plunges right into the core. Drawing from her experience as an ICU nurse, NFL cheerleader, and being The Bachelorette- Gabby is able to bring a unique perspective to each conversation. With discussions covering serious and relatable topics but approached from relatability and heart (along with Gabby’s wicked sense of humor— of course).
Andy Kaufman for Women
3d ago
Gabby is an absurdist/genius/artiste just in time for the death spiral of late stage capitalism. Would love to smoke a cigarette with her à la “Heathers” when the asteroid hits.
Love the episodes with Robby
3d ago
This podcast is so fun and wonderful.
Most annoying voice ever
3d ago
HOW do you people listen to this? This sounds like a combination of SNL’s Girl-You-Should-Never-Start-A-Conversation with and the random crazy lady on the bus complaining about chemtrails
A Brilliantly Beautiful Run-On Sentence
3d ago
I’ve been a card-carrying Gabby Stan since the dawn of time (or at least since she graced our screens with her unhinged charm), but this podcast? This podcast has unlocked a whole new level of devotion. We’re talking full-throttle, can’t-stop-listening, laugh-so-loud-my-downstairs-neighbor-thinks-I’m-having-an-episode devotion. (Welcome to NYC, where walls are thin, and personal space is a myth.) Gabby’s brain is a labyrinth of brilliance, sarcasm, and existential hilarity—crafted by the comedy gods and delivered in speech cadences that could power a metronome factory. Her topics? Unhinged and yet so on point. Her under-the-breath remarks? A masterclass in high-IQ snark. Her ability to weave together a thought so chaotically yet cohesively? Borderline sorcery. Listening to Long Winded is like stepping into a world where brutal truths are delivered on a bedazzled platter of self-awareness and wit—only Gabby could make reality checks feel like a spa day for the soul. Her run-on sentences alone should have their own fan club. So brava, KWEEN! Rise, reign, and ramble on—we are here for every last winded, wonderful second.
About
Information
- Channel
- CreatorDear Media
- Years Active2024 - 2025
- Episodes51
- RatingExplicit
- Show Website
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