Podcast Summary: "Long Winded with Gabby Windey"

Episode: Audrey Hobert
Date: November 13, 2025
Host: Gabby Windey
Guest: Audrey Hobert

Episode Overview

This episode features a lively, candid, and thoughtful conversation between host Gabby Windey and indie musician-songwriter Audrey Hobert. The duo dives deep into the realities of creativity, the messiness of the entertainment industry, modern relationships, sexuality, mental health, and, of course, a healthy smattering of pop culture hot takes. Gabby’s humor and openness pair perfectly with Audrey’s reflective and grounded style, resulting in a refreshingly honest dialogue about art, identity, discipline, and living a full life.

Major Discussion Topics & Key Moments

1. Life Rhythms, Productivity, and Mental Health

[03:01 – 06:17]

• Both Gabby and Audrey talk about the unpredictable rhythms of creative industries.
• Gabby admits to feeling overwhelmed at times and needing structure:
  "I feel like the industry—it comes in waves. For two weeks I’m not doing anything, and then next week I’m so busy I wanna kill myself." (Gabby, 04:06)
• They agree being busy keeps their minds occupied and less anxious.

2. Astrology & Identity

[04:54 – 05:55]

• Gabby quizzes Audrey about her zodiac sign; Audrey is a Pisces and describes it as "sensitive and daydreamy."
• Lighthearted banter about astrology and the supposed genius of Gemini women.

3. The Creative Process & Writing Songs

[12:26 – 15:12]

• Gabby expresses admiration for Audrey’s songwriting, likening it to poetry.
• Audrey, self-effacing, says her writing is “direct” rather than “poetic.”
  "My hope would be [to] distill a large thought down to one line that sticks with you… hopefully that’s every line of the song." (Audrey, 13:00)
• Discussion on the pressure of following up a successful first album.

4. Balancing Work and Inspiration

[17:11 – 19:35]

• Gabby vents about the challenges of writing a book of essays, struggling with deadlines, and the slow process of seeing essays come to fruition.
• Audrey relates, saying, "Having this fear is going to take you out of your life… you’re going to be always worrying, ‘is this enough to inspire me?’” (Audrey, 18:27)

5. Mining Personal Life for Art

[19:44 – 22:04]

• Audrey openly shares how she writes autobiographical songs, sometimes drawing from past breakups and crushes.
• Gabby reflects on Joan Didion’s quote: “As a writer, you have to sell people out.”
• Songs about relationships are discussed candidly (e.g., "Sue Me" and "Wet Hair" about an ex).

6. Sex, Dating, and Sexuality

[22:45 – 29:03]

• The pair get personal and hilarious about modern dating, men’s “headboard” habits, and the transition into sleeping with women.
• Gabby:
  "Men are just like big animals. No offense. It really feels like the wild. There’s like, grunts and noises." (Gabby, 27:19)
• Both share their preference for authenticity—valuing involuntary over performative reactions in intimacy.

7. Weed, Creativity & Routines

[11:00 – 31:23]

• They trade stories on weed routines. Audrey prefers daytime weed for creative walks; Gabby describes a nightly routine.
• The pair bond over “wake and bake” walks, creative stretches, and the challenges of socializing when high.

8. Pop Culture Deep Dives

[06:53 – 09:18], [33:02 – 36:11], [43:16 – 46:47]

• A tangent about Jane Mansfield, Marilyn Monroe, and Mariska Hargitay.
• Audiences learn about Gabby’s fascination with "Real Housewives", Jen Shah’s arrest, and the bizarre crossovers of reality TV crime and scams.
• Both marvel at the collaborative potential of infamous women like Jen Shah and Elizabeth Holmes:
  "If they wrote a book together… paragraph for paragraph, a novel? I’d buy it.” (Audrey, 34:28)

9. Age, LA Culture & Aspirations

[32:51 – 35:43]

• Gabby and Audrey reflect on the pressures of aging in LA.
• They note how women in other cities carry themselves versus LA’s "effed-up" standards:
  "Go to any other place and I see women whose shoulders are back because they’re not in LA." (Audrey, 33:13)
• Gabby finds Real Housewives of New York inspiring for aging unapologetically.

10. Social Media, Dopamine & Discipline

[52:18 – 54:41]

• Both discuss the overwhelming nature of social media—how doomscrolling affects their mood and creativity.
• Audrey uses lock boxes to limit phone use; Gabby relates to the dopamine chase.
• Insight into balancing authenticity and strategy on platforms like TikTok and Instagram.

11. Family, Relationships & Chosen Family

[62:07 – 64:13]

• Gabby discusses marrying into a large, loving Orthodox Jewish family and the joys and challenges that come with it.
• Audrey describes her role as the eldest of four, how family shaped her, and longing for togetherness on holidays.

12. Artistic Identity & The Role of an “Artist”

[47:41 – 48:44]

• Audrey mentions Miley Cyrus’ reflection:
  "I’m not an artist. I’m in a deal… this is a job. One day I’ll get to be an artist." (Audrey paraphrasing Miley, 48:09)
• Discussion about the pressure to produce, and the elusive feelings of artistic fulfillment.

Notable Quotes & Memorable Moments

• On Productivity:
  "Sometimes, like, it… comes in waves. …The next week you’re so busy you wanna kill yourself."
  — Gabby, [04:13]

• On Songwriting:
  "It is like poetry… but I always felt my writing was just direct."
  — Audrey, [13:00]

• On Creativity and Fear:
  "Having this fear is going to take you out of your life. …I don’t want to be someone who wrecks my own life so that I have something to write.”
  — Audrey, [18:27]

• On Dating Men:
  "Men are just like big animals. No offense. It really feels like the wild. …Now I’m sleeping with a woman anyway. And she can moan like one."
  — Gabby, [27:19]

• On Social Media Addiction:
  "It’s an addiction. …That giant orange bar, I’m like, 'whoa, whoa' for like two seconds."
  — Audrey, [53:04]

• On Being an Artist (paraphrasing Miley Cyrus):
  "I can’t consider myself an artist. …I’m in a deal. This is a job. One day I’ll get to be an artist."
  — Audrey, [48:09]

Timestamps for Key Segments

• [03:01] — Discussion of feeling overwhelmed in creative work
• [04:54] — Astrology, identity, and discipline
• [12:26] — Gabby asks about Audrey’s songwriting process
• [17:11] — Struggles of writing, deadlines, and creative blocks
• [19:44] — Putting real relationships into art
• [22:45] — Sex, headboards, and the joys of dating women
• [27:19] — Gabby’s “men as animals” riff
• [31:23] — Experiences with weed and creativity
• [33:13] — Reflections on aging in LA and elsewhere
• [34:28] — Jen Shah and Elizabeth Holmes potential book
• [47:41] — Reflections on artistic identity (Miley Cyrus quote)
• [52:18] — Social media overwhelm and boundaries
• [62:07] — Gabby on marrying into a big family; family dynamics
• [64:13] — Audrey on being the eldest sibling and family ties

The Tone & Vibe

The episode is casual, authentic, and peppered with humor—raw but also deeply thoughtful. Both Gabby and Audrey are unafraid to discuss moments of self-doubt, anxiety, and the push-pull between ambition and peace. The conversation moves smoothly from lighthearted pop culture references to honest disclosures about mental health and the creative grind. Their easy chemistry and quick wit make for a genuinely engaging listen for fans of creative process, queer culture, and the realities of life in the public eye.

Closing Notes

This episode stands out for its vulnerability, insight, and celebration of honest creativity. Both the host and guest offer refreshingly unfiltered perspectives on what it means to make art, live authentically, and find meaning in the messiness of it all.

Audrey Hobert social links:

• Instagram: [Audrey Hobert]
• TikTok: Mike Monster
• Twitter: Mike Monster1
• Substack: Mike Monster
• YouTube: Audrey Hobert

[Timestamps provided in MM:SS format. Content trimmed for brevity and focus on key conversational sections.]