Podcast Summary: Long Winded with Gabby Windey

Episode: who's this diva cup #2
Host: Gabby Windey
Date: February 26, 2026

Episode Overview

In this solo episode, Gabby Windey delivers an unfiltered, comedic, and deeply personal monologue, riffing on health challenges, her tumultuous relationship with medication, the realities of mental health, social expectations, internet fame, and an unforgettable (and graphic) account of her attempt to use a Diva Cup. Gabby navigates a series of interconnected rants that are both honest and humorous, providing fresh takes on pop culture, wellness, gender, and the pressures of public attention—all through her signature self-deprecating wit.

Key Discussion Points & Insights

1. Health & Medication Struggles

• Gabby opens by detailing her current state—withdrawal from multiple medications after a bout of bronchitis, steroids, and codeine cough syrup. She uses self-awareness and humor to discuss the physical and emotional toll this has taken.

  • Medication Withdrawal Experience

    • Suffering side effects from steroids ("I may seem different to you, and that's just because I took a puff of an inhaler filled with epinephrine. My heart's beating out of my chest..." [01:02])
    • Navigating withdrawal from multiple drugs: prednisone, Lamictal, gabapentin, and codeine.
    • Shock at codeine's addictive quality: “I was asleep for two days. It’s like, what is going on? I’ve never been this tired in my life. This is that COVID tired people are talking about. I’m not getting enough oxygen to my brain. I’m hypoxic.” [01:45]
    • Frustration with mental health meds: “My antidepressant is turning against me. It’s the body or it’s the mind. It’s your right to be happy and healthy, they say. No, it’s not. You must choose one.” [03:35]

  • Self-Experimentation & Tapering

    • Gabby describes taking matters into her own hands, cutting doses, and boosting vitamin intake, underlining the complexity and frustration of finding effective psychiatric care.

2. Fame, Authenticity, and Boundaries

• Gabby reflects on her sudden surge in popularity after a viral TikTok, grappling with attention, expectations, and the ironies of influencer culture.

  • Social Media & Audience Dynamics

    • On being “catapulted” to relevance: “I didn’t even need the leaked nude tape. I just needed Bella Hadid to repost my TikTok. Now I’m catapulted to the stratosphere.” [08:47]
    • The mixed blessing of growing an audience: “This is me with 10,000 views on YouTube. This is the most relevancy and I can’t take it. It’s about 2,000 too much.” [22:44]
    • The incoming “Love the pod but…” messages: Gabby humorously dreads the inevitable criticism from new, less familiar listeners—fearing “Love the POD but” DMs about every pop culture take or candid opinion she’s ever shared. [23:36]

  • Industry’s Demand for Conformity

    • Gabby jokes about talent requests specifying “female, mid-30s, positive personality, non-polarizing”—critiquing how the media pigeonholes personalities and her refusal to fit neatly into expectations:
      • “Positive personality and non-polarizing. Get out of my face. Do you know anything about me?” [21:40]
      • “The most offensive of them all. Of course I want to be polarizing. Are you crazy? I don’t want to appeal to the masses…” [22:44]

3. Smoking as Social Signifier

• In a lengthy aside, Gabby deconstructs the social function and stigma of smoking, situating it as a communal act, a rebellion, and a coping mechanism for trauma.

  • “Smoking is a sign of something else. It’s a community. You’re calling in like-minded people. Of course we have to leave this bar and talk collectively on the one person here that we hate.” [14:31]
  • “Smoking is inherently cool and sexy and that’s what you will think of me if I have anything to do with it. But I don’t care. I don’t care.” [16:05]

4. Pop Culture & Internet Commentary

• Gabby lightly roasts Megyn Kelly, the contradictions of internet discourse, and the fickle nature of public opinion on women’s roles and non-binary inclusivity.

  • On Megyn Kelly’s controversial tweet and audience backlash: “You can have a job and kids with a man who loves you. Extremely offensive. Her demo hated that. Dissenters among them. They turned on her.” [18:55]
  • Her own position: “I’m not pandering. Okay? Okay. And now people, now everyone wants a little of this. They want a piece.” [20:15]

5. Diva Cup Saga: A Relatable Disaster

• The centerpiece rant of the episode: Gabby chronicles—with graphic, irreverent detail—her misadventures using a Diva Cup.

  • Learning Curve and Messiness

    • The difficulty of insertion, the physical contortions required, and the resulting mess:
      • “You gotta fold it like a hot dog, then you gotta fold it like a hamburger… Actually, let me fold it like a quesadilla…” [38:16]
      • “Fingering yourself with all ten fingers in a suction vacuum cup that’s holding your uterine lining. It said to vacuum in just the right way, to hug every single ridge of your uniquely shaped vagina.” [39:10]

  • Getting Stuck & The Absurdity of Removal

    • When the cup won’t come out: “No amount of force of pull from any part of your body or hand can dislodge the negative pressure this vacuum funnel has created in your vagina… Come on. I have no other choice but to call the ambulance. So once I figure out the number to 91 1, I get on the phone with the paramedic.” [40:20]
    • On the cleanup aftermath: “Everything’s gonna be fine. I’m going to be free. Goes the diva cup. Splashes everywhere. You’re not getting it in the toilet. You’re getting it on the toilet bowl, a little in the toilet, some on your white bathroom floor…” [42:07]

  • Sanitization & Social Commentary

    • The indignity of boiling the cup: “And now you have to look your friends in the face knowing where that noodle came from and what it is coated with. Pussy blood. Enjoy. Enjoy. It’s a red sauce.” [42:45]
    • Gabby ties this back to the broader issues of gender labor and the unequal burdens women bear out of “sustainability”—“your husband is mining for crypto but all of the weight falls on us because we’re women. So we’re back in the 1800s.” [43:30]

6. Vintage Furs, PETA, and Ethical Contradictions

• Gabby closes with a story about wearing vintage fur, criticizing PETA’s lack of compassion in the infamous Tonka the chimpanzee case, and reflecting on moral ambiguity.

  • “I haven’t been DM’d by PETA only once, I’ll tell you that. And I learned quickly and I moved swiftly. I got a protection order and I blocked their ass. You can’t get to me. No, because it’s vintage. Not because I take a moral high ground. Because it’s cool. Because we’re shopping vintage. Because it sounds better if I can say my fur is from the 70s.” [44:57]
  • On PETA’s leadership in the Tonka case: “They weren’t compassionate. No. They were smug as fuck. They had a terrible leader of representation. He cannot be your figurehead. No, no. He had not once one ounce of compassion for Tanya, our beloved monkey mother…” [45:45]

Notable Quotes & Memorable Moments

Health & Withdrawal

• “It’s the body or it’s the mind. It’s your right to be happy and healthy, they say. No, it’s not. You must choose one.” — Gabby (03:35)

On Smoking & Social Rebellion

• “Smoking is inherently cool and sexy and that’s what you will think of me if I have anything to do with it. But I don’t care. I don’t care.” — Gabby (16:05)

On Media Requests for "Non-Polarizing" Women

• “Do you know anything about me? Have you ever been around these parts before? You saw one clip and you think you know it all… Positive personality and non-polarizing. Get out of my face.” — Gabby (21:40)

Diva Cup Disaster

• “Fingering yourself with all ten fingers in a suction vacuum cup that’s holding your uterine lining… All in vain. Double entendre. A vein holds the blood. There’s blood everywhere. And you’re under duress and 10 minutes late for work…” — Gabby (39:10)
• “No amount of force or pull… can dislodge the negative pressure this vacuum funnel has created in your vagina. Nothing can pull it out… I have no other choice but to call the ambulance. So once I figure out the number to 91 1…” — Gabby (40:20)
• “You have to put it in a pot of boiling water. This is the same pot that I cook spicy riggy in once a week for guests. And now it has a history.” — Gabby (42:45)

On Vintage Fur and PETA

• “No, because obviously it’s vintage. Not because I take a moral high ground. Because it’s cool. Because we’re shopping vintage. Because it sounds better if I can say my fur is from the 70s.” — Gabby (44:57)
• “They [PETA] weren’t compassionate. No. They were smug as fuck… Why are you going for our mayor, Tanya? She loved Tonka. You could have sat down with her… Have a heart. Have a soul.” — Gabby (45:45)

Timestamps for Important Segments

• [01:02–07:00] — Gabby’s health struggles; medication withdrawal; life as a nurse-patient hybrid.
• [08:23–14:30] — Navigating new fame, social expectations, and being polarizing; influencer culture satire.
• [14:31–18:50] — The psychology and social dynamics of smoking; generational hypocrisy.
• [18:55–22:44] — Pop culture commentary; Megyn Kelly, audience backlash, and performative feminism.
• [23:36–29:00] — “Love the pod but…” complaints; navigating internet criticism and viral attention.
• [38:16–43:30] — Full Diva Cup saga: the graphic, comedic ordeal from insertion to removal to sanitation.
• [44:57–47:00] — Vintage fur, PETA, ethical gray areas, and the Tonka/Tanya chimpanzee saga.

Tone & Delivery

Gabby’s comedic voice is acerbic, self-deprecating, and fearlessly candid. She uses hyperbole, vivid imagery, and layered metaphors to expose anxieties about health, gender roles, internet culture, and the farce of “relatability” in the influencer age. Jokes and satire operate alongside earnest admissions of struggle, resulting in a raw and highly engaging listen.

Takeaway

This episode is a whirlwind of personal storytelling and societal satire. Gabby Windey invites listeners into her chaotic world by stripping away the façade of wellness and Insta-perfection, finding dark humor in the messiest aspects of health, womanhood, fame, and the never-ending chase for approval—from others and herself. The Diva Cup story, in particular, stands as a hysterical yet sobering metaphor for the ordeal of trying (and failing) to meet impossible standards—whether they be for sustainability, beauty, or “non-polarizing” appeal.