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Home - Embracing Vulnerability and Breaking the Chains of Toxic Masculinity: A Journey of Self-Discovery with Gregg Ostrin
RECOVERY PODCASTLAND

Embracing Vulnerability and Breaking the Chains of Toxic Masculinity: A Journey of Self-Discovery with Gregg Ostrin

Megan SwanBy Megan SwanMay 29, 20244 Mins Read
The Spy Who Went Into Rehab Gregg Ostrin
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The Spy Who Went Into Rehab Gregg Ostrin

In the latest episode of “Wellness As A Way of Life,” I sat down with guest Gregg Ostrin to explore his profound journey of overcoming toxic masculinity, addiction, and societal expectations. Through candid conversations and personal reflections, Gregg shared his experiences of finding solace, self-discovery, and, ultimately, empowerment. He made a point of telling me how, ‘thanks to’ the pandemic, he started going to meetings again every day, and this time around, he found a deeper fellowship and spiritual connection.

Gregg Ostrin: Breaking Free from Societal Expectations:

Growing up feeling inadequate under the weight of his father’s expectations, Gregg sought solace in the world of theater and imagination. He candidly discusses how he didn’t conform to traditional male stereotypes, finding comfort in his relationships with gay friends and embracing his unique identity. This rejection of societal norms paved the way for him to embark on a journey of self-discovery and redefine his understanding of masculinity.

Gregg Ostrin: Exploring the Power of Sobriety and Self-Reflection:

With 37 years of sobriety under his belt, Gregg delves into the transformative power of addiction recovery and the importance of self-awareness. Through his personal experiences and reflections, he emphasizes the crucial role of communication and introspection in breaking the cycle of toxic masculinity and fostering meaningful connections. Gregg’s journey inspires others to confront their vulnerabilities and embrace authenticity. I appreciated his candor and humor.

Gregg Ostrin: From Personal Struggles to Creative Expression:

Ostrin’s creative outlet, the play “The Spy Who Went Into Rehab,” is a comedic exploration of sobriety, masculinity, and the complexities of human relationships. Ostrin sheds light on the nuanced intersections of personal growth and societal influence by weaving together themes of addiction and societal expectations. The play challenges cultural norms on what it means to be masculine and invites audiences to reflect on their own beliefs and perceptions.

Gregg Ostrin: Empowering Through Vulnerability and Intimacy:

Throughout the episode, Gregg reflected on his evolving views on intimacy, respect, and gender dynamics. He candidly shared his journey of unlearning toxic behaviors and embracing vulnerability in his relationships. By dismantling stereotypes and fostering genuine connections, he mentioned he also has a brilliant, outspoken daughter who has no issue calling him out when he says something “mansplaining-y.”

Gregg Ostrin: Navigating Cultural Shifts and Embracing Change:

In the wake of movements like #MeToo and Black Lives Matter, I appreciate that he emphasized the importance of understanding one’s biases and embracing cultural evolution. By acknowledging the impact of societal shifts on personal growth, Gregg underscores the significance of empathy, inclusivity, and continuous self-reflection. Through his personal anecdotes and insightful reflections, Ostrin inspires listeners to challenge ingrained beliefs and strive for a more inclusive and compassionate world.

As the episode draws close, Gregg’s journey is a testament to the transformative power of vulnerability, sobriety, and self-awareness. By sharing his story with honesty and humor, Gregg invites us to support his new play, The Spy Who Went Into Rehab, which opens June 7th in Venice Beach. Get your tickets here. 

Listen to my full conversation with him here. (May 28th Publish Date)

THE SPY WHO WENT INTO REHAB, Opens June 7th

Tickets: https://pacificresidenttheatre.org/the-spy-who-went-into-rehab/


Wellness as a Way of Life podcast w/ Megan Swan: Gregg Ostrin

Listen here on APPLE podcasts


Sober in Los Angeles at Cha-Cha-Cha

WHAT A TRIP! Sober Curator Contributor Megan Swan recently recapped her whirlwind 72 hours in Los Angeles, which included a stop at Cafe Gratitude in Venice, CA. Sober Curator Pro Tip: Why not make a reservation for dinner at Cafe Gratitude before heading to see The Spy Who Went Into Rehab at the Pacific Resident Theatre? Sounds like the perfect sober date night to us! (BTW date night can be with anyone you love spending time with) 72 Hour Sober in LA – What a Trip! « The Sober Curator


The Spy Who Went Into Rehab

SOBRIETY IN THE CITY: A Sobering Look: The Spy Who Went Into Rehab by Gregg Ostrin « The Sober Curator


Recovery Podcastland by the Sober Curator

RECOVERY PODCASTLAND:

Welcome to RECOVERY PODCASTLAND, your audio haven for all things recovery! With an overwhelming number of engaging podcasts constantly updating each week, it can be hard to keep up. That’s where The Sober Curator steps in!

We’re tirelessly curating and producing original podcast content with a focus on recovery, so you don’t have to wade through the noise. Sober Curator Pro Tip: Tune into our recommended podcasts while driving, dog-walking, working out, house-cleaning, crafting, prepping for the day, or cooking. It’s a perfect way to infuse your daily routine with a dose of recovery inspiration.


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Megan Swan
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Megan Swan is an expert at holding intuitive compassionate space for people. She loves to inspire others to live life to fullest and expand their vision of what they are capable of. She also loved dancing on top of the bar, now she just does that on Instagram.

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Spain – El Camino- the Last 100
May 12 - May 21

Spain – El Camino- the Last 100

$3297
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Spain – El Camino- the Last 100
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Spain – El Camino- the Last 100

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Florida Roundup 2026
May 13 @ 12:00 pm - May 17 @ 1:00 pm EDT

Florida Roundup 2026

The Westin Fort Lauderdale Beach Resort 321 North Fort Lauderdale Beach Boulevard, Fort Lauderdale
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5:00 pm
Hot Gurlz Pre-Summer Reset Pajama Party
May 13 @ 5:00 pm - 8:00 pm PDT

Hot Gurlz Pre-Summer Reset Pajama Party

Penelope & The Beauty Bar
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Spain – El Camino- the Last 100
May 12 - May 21

Spain – El Camino- the Last 100

$3297
Ongoing
Florida Roundup 2026
May 13 @ 12:00 pm - May 17 @ 1:00 pm EDT

Florida Roundup 2026

The Westin Fort Lauderdale Beach Resort 321 North Fort Lauderdale Beach Boulevard, Fort Lauderdale
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6:00 pm
Sip to Sustain: Zero‑Proof Mocktails & Rituals for the Season of More
May 14 @ 6:30 pm - 8:30 pm CDT

Sip to Sustain: Zero‑Proof Mocktails & Rituals for the Season of More

Warrior Nutrition 1093A Upper Valley Pike Springfield, OH 45504, Springfield
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All Day
Spain – El Camino- the Last 100
May 12 - May 21

Spain – El Camino- the Last 100

$3297
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Florida Roundup 2026
May 13 @ 12:00 pm - May 17 @ 1:00 pm EDT

Florida Roundup 2026

The Westin Fort Lauderdale Beach Resort 321 North Fort Lauderdale Beach Boulevard, Fort Lauderdale
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6:00 pm
SOBER IS THE NEW COOL NYC WHITE PARTY
May 15 @ 6:00 pm - 9:00 pm EDT

SOBER IS THE NEW COOL NYC WHITE PARTY

The Maze
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Celebrating 20 Years with our “Steps to Recovery” Comedy Social
May 15 @ 6:30 pm - 8:30 pm EDT

Celebrating 20 Years with our “Steps to Recovery” Comedy Social

Lipkin Theatre at Northampton Community College 3835 Green Pond Road, Bethlehem
$29.00
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All Day
Spain – El Camino- the Last 100
May 12 - May 21

Spain – El Camino- the Last 100

$3297
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Florida Roundup 2026
May 13 @ 12:00 pm - May 17 @ 1:00 pm EDT

Florida Roundup 2026

The Westin Fort Lauderdale Beach Resort 321 North Fort Lauderdale Beach Boulevard, Fort Lauderdale
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All Day
Spain – El Camino- the Last 100
May 12 - May 21

Spain – El Camino- the Last 100

$3297
Ongoing
Florida Roundup 2026
May 13 @ 12:00 pm - May 17 @ 1:00 pm EDT

Florida Roundup 2026

The Westin Fort Lauderdale Beach Resort 321 North Fort Lauderdale Beach Boulevard, Fort Lauderdale
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11:00 am
Creative Kaleidoscope: Morning Altars Workshop | Teetotal Initiative Pittsburgh
May 17 @ 11:00 am - 2:00 pm EDT

Creative Kaleidoscope: Morning Altars Workshop | Teetotal Initiative Pittsburgh

Lake Point Shelter Pittsburgh
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May 12 - May 21

Spain – El Camino- the Last 100

Spain – El Camino- the Last 100

May 12 - May 21

Spain – El Camino- the Last 100

About this trip Walking from Sarria to Santiago is a delightful journey that offers a wonderful blend of scenery and culture. This section features gently rolling hills, lush forests, and

$3297
May 12 - May 21

Spain – El Camino- the Last 100

May 13 @ 12:00 pm - May 17 @ 1:00 pm <span class='timezone'> EDT </span>

Florida Roundup 2026

Florida Roundup 2026

May 13 @ 12:00 pm - May 17 @ 1:00 pm EDT

Florida Roundup 2026

Florida Roundup 2026 Peace! Love! Sober! - JOIN US AT FLORIDA ROUNDUP 2026!! FLORIDA ROUNDUP 2026 is excited to welcome you all back to The Westin Fort Lauderdale Beach for

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May 12 - May 21

Spain – El Camino- the Last 100

May 13 @ 12:00 pm - May 17 @ 1:00 pm <span class='timezone'> EDT </span>

Florida Roundup 2026

May 12 - May 21

Spain – El Camino- the Last 100

May 13 @ 12:00 pm - May 17 @ 1:00 pm <span class='timezone'> EDT </span>

Florida Roundup 2026

May 12 - May 21

Spain – El Camino- the Last 100

May 13 @ 12:00 pm - May 17 @ 1:00 pm <span class='timezone'> EDT </span>

Florida Roundup 2026

May 12 - May 21

Spain – El Camino- the Last 100

May 13 @ 12:00 pm - May 17 @ 1:00 pm <span class='timezone'> EDT </span>

Florida Roundup 2026

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Wednesday, May 13, 2026

  • May 13, 2026 5:00 pm - 8:00 pm
    Hot Gurlz Pre-Summer Reset Pajama Party
  • May 13 @ 5:00 pm - 8:00 pm PDT

    Hot Gurlz Pre-Summer Reset Pajama Party

    Hot Gurlz Pre-Summer Reset Pajama Party An elevated evening celebrating a new way to gather, set within the luxurious surroundings of Penelope & The Beauty Bar at the Fairmont Olympic

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    May 13, 2026 6:00 pm - 7:00 pm
    Recovery Takes Center Stage: A BACKSTAGE Conversation with Sean Daniels
  • Virtual Event
    May 13 @ 6:00 pm - 7:00 pm PDT

    Recovery Takes Center Stage: A BACKSTAGE Conversation with Sean Daniels

    BACKSTAGE with The Sober Curator: Media Night | Coming Soon Recovery takes center stage in this special Backstage with The Sober Curator conversation with Sean Daniels, playwright of The White

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  • May 13, 2026 7:00 pm - 9:00 pm
    The Great Curious Cocktail Party — Central Ohio Edition
  • May 13 @ 7:00 pm - 9:00 pm EDT

    The Great Curious Cocktail Party — Central Ohio Edition

    The Great Curious Cocktail Party — Central Ohio Edition Explore four zero‑proof Curious Elixirs with paired bites, garnishes, and self‑guided creative moments in a warm, modern space. Party with Purpose.

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Thursday, May 14, 2026

  • May 14, 2026 6:30 pm - 8:30 pm
    Sip to Sustain: Zero‑Proof Mocktails & Rituals for the Season of More
  • May 14 @ 6:30 pm - 8:30 pm CDT

    Sip to Sustain: Zero‑Proof Mocktails & Rituals for the Season of More

    Sip to Sustain: Zero‑Proof Mocktails & Rituals for the Season of More Modern mocktails, grounding rituals, and everyday boosters for energy, clarity, and recovery. A calm moment inside May’s busiest

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    Drag Bingo | Sober AF Bottle Shop
  • May 14 @ 7:00 pm - 9:00 pm PDT

    Drag Bingo | Sober AF Bottle Shop

    Drag Bingo | Sober AF Bottle Shop 6 rounds of laughs and fun with Queen Sativa Drag Bingo! 💅🎉 Drag Bingo with Queen Sativa 🎉💅 Every second Thursday of the month,

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Friday, May 15, 2026

  • May 15, 2026 6:00 pm - 9:00 pm
    SOBER IS THE NEW COOL NYC WHITE PARTY
  • May 15 @ 6:00 pm - 9:00 pm EDT

    SOBER IS THE NEW COOL NYC WHITE PARTY

    SOBER IS THE NEW COOL NYC WHITE PARTY Step into a night where hearts shine brighter than the skyline Sober Is The New Cool White Party in New York City

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  • May 15, 2026 6:30 pm - 8:30 pm
    Celebrating 20 Years with our “Steps to Recovery” Comedy Social
  • May 15 @ 6:30 pm - 8:30 pm EDT

    Celebrating 20 Years with our “Steps to Recovery” Comedy Social

    Celebrating 20 Years with our "Steps to Recovery" Comedy Social Overview Join us for a night of laughter and celebration as RR celebrates 20 years of service by hosting our

    $29.00
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  • May 17, 2026 11:00 am - 2:00 pm
    Creative Kaleidoscope: Morning Altars Workshop | Teetotal Initiative Pittsburgh
  • May 17 @ 11:00 am - 2:00 pm EDT

    Creative Kaleidoscope: Morning Altars Workshop | Teetotal Initiative Pittsburgh

    Creative Kaleidoscope: Morning Altars Workshop | Teetotal Initiative Pittsburgh About the event: Morning Altars Workshop Join us for a nourishing and creative afternoon at our Morning Altars Workshop, a guided

  • May 17, 2026 3:30 pm - 5:00 pm
    Bar Nun: Dry social – 05/17/2026
  • May 17 @ 3:30 pm - 5:00 pm EDT

    Bar Nun: Dry social – 05/17/2026

    Bar Nun: Dry social - 05/17/2026 Make new local friends! Bar Nun is hosting chill dry socials to meet your Bushwick and Ridgewood, NY neighbors every Sunday afternoon. Join relaxing

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