RISK! Podcast: "How Embarrassing"

Date: January 1, 2026
Host: Kevin Allison

Overview

This episode of RISK! is dedicated to the theme of embarrassment—the mortifying, cringeworthy, and deeply human moments that most people would do anything to hide. Host Kevin Allison curates four true stories ranging from the hilariously gross to the unexpectedly profound, all centering on humiliation and the lessons (sometimes) learned. The storytellers deliver uncensored accounts that balance humor with honesty, reminding listeners that shame, missteps, and awkwardness are a universal part of life.

Key Stories & Discussion Points

1. "Mother's Little Helper" by Donna Steele

Timestamps: [02:25] – [13:35]

Summary

Donna recalls her mother's obsession with appearances and cleanliness, a facade that crumbled in spectacularly embarrassing fashion during a shopping trip. When her mom urgently needs a bathroom but can't make it, she ends up defecating in a McDonald's cup in a crowded Levi’s store dressing room—forcing Donna to face the ultimate test of daughterly duty.

Memorable Moments & Quotes

• The Coke Obsession:
  “She could tell the difference between Coca Cola from one McDonald’s location, like on Parham Road to the other... If it wasn’t from McDonald’s, she would know if you got it from Wendy’s or Burger King, she would flip out, flip out.” [02:42]

• The Unthinkable Happens:
  “I see my mother crouching in the corner of the fitting room... And that damn McDonald’s cup...there’s shit spray around the cup and there’s like a little puddle next to it.” [04:08]

• Donna's Refusal:
  “Mom, I cannot carry your cup of poop through a crowd of 70 people to throw it away.” [05:18]

• Relentless Poise:
  “She walks outside of the Levi’s store and sits on the bench that is right next to the trash can facing the store...walking around Short Pump Mall like she doesn’t give a shit.” [09:11]

• Reflection:
  “It amazes me how my mom continuously wants people to think that she’s all put together and how she’s able to do it even when she’s a complete mess.” [12:40]

Takeaway

Despite her mom’s mortifying public episodes, Donna ends with an odd sense of respect for her mother’s unflappable image management—even amidst total disaster.

2. "Kevin's First (and Last) Attempt at Prostitution" by Kevin Allison

Timestamps: [14:41] – [30:34]

Summary

Kevin shares a comically disastrous memory from his early 20s, stuck in financial limbo and considering his more streetwise roommate’s suggestion: try a little “hustling.” Encouraged by his roommate Ray’s “Seven Laws of Successful Whoring,” Kevin ventures timidly into a hustler bar—only to encounter derision, a sketchy client, and a backseat debacle in a NYC cab that ends in humiliation on the street, but ultimately, unexpected relief and self-assertion.

Notable Quotes

• On self-doubt:
  “I didn’t feel like I was competent at anything except for sketch comedy ... I felt like the only thing I was really good at was scanning the sidewalk for nickels.” [14:56]

• Roommate’s Advice:
  “Sweetie Phone Home ... Money Before Honey ... Hard to Get’s an Easy Bet.” [16:39]

• First Encounter:
  “He took my hand and he raised it up into the light and he showed it to a friend of his. And he said to his friend, ‘Look at that hair on the back of his hand. That means there's hair on his ass, too.’” [19:14]

• Disaster in the Cab:
  “So much for money before honey, Donna Summer would have been livid.” [25:08]
  “‘Shut up and put your dick in my mouth.’ ... And the driver of the cab’s looking back like, ‘Oh, yeah, here’s the shut up and put your dick in my mouth moment.’” [26:54]

• Public Realization:
  “I just let it rip. I yell at him, ‘The next time you want to suck my cock, you can pay for it first!’ And I slammed the door ... two dozen people on Sixth Avenue were staring at me.” [29:15]

Takeaway

Kevin escapes both physical and existential danger, learning that hustling isn’t for him—soon after, he receives news that his comedy group’s pilot was picked up, a cosmic sign that he’s better off sticking to his true calling (and not pretending to like things he doesn’t).

3. "We Could Do a Million Other Things" by Darren Infinity

Timestamps: [33:29] – [40:27]

Summary

Darren recounts a night at a men’s BDSM party where an eagerly anticipated scene with a handsome “daddy” goes south when his partner realizes he forgot his erectile dysfunction pills. The ensuing shame is palpable, and Darren wishes he knew then how to reassure that sex is about more than performance.

Notable Quotes

• Setting the Scene:
  “He had this very daddy energy to him. Had those laugh lines that told you that he’d walked a few miles but done so with a smile on his face.” [33:52]

• The Turn:
  “...he puts his hand on mine and says, ‘I forgot my pills.’ ... and his whole face just showed that he was so upset with himself and with the situation.” [36:53]

• Wish for Better Words:
  “I still wish I’d had the words to tell this beautiful man that it didn’t matter that he forgot his pills, that his sexuality was his whole person, not just what was in his pants.” [38:44]

• Lesson Shared:
  “That’s why I teach now ... so that people will have language to tell each other that it’s okay, that sometimes things don’t work the way we would like them to work. And that doesn’t make us any lesser than.” [39:38]

Takeaway

The story moves from embarrassment to compassion, highlighting the importance of communication and acceptance in sex-positive spaces.

4. "Paraguay Gone Wrong" by Jen Bosworth

Timestamps: [40:27] – [57:27]

Summary

Jen delivers a wild, darkly comedic story of her teenage summer volunteering in Paraguay (instead of her Columbia dream). Stranded due to her mother’s caution and idiosyncrasies, Jen finds herself isolated, broke, and ultimately on the verge of being sold into sexual slavery—only escaping by wetting herself, inspired by a childhood classmate’s trick to dodge gym class.

Memorable Quotes & Moments

• On Not Offending Hosts:
  “You cannot offend the host family ever. They may look different ... may not have as many things as you... Do not offend them.” [41:36]

• Spanish Vocabulary:
  “I grew up thinking that everybody’s mom spoke in Spanish when they were cussing somebody out.” [43:34]

• The Money's Gone:
  “Motherfucker, how am I gonna get my motherfuckin cigarettes? Because if you’re a smoker, you know...” [46:24]

• The Sale:
  “This mentor wasn’t a mentor. She was a pimp. And it hit me after I came to... I’m being sold as a prostitute to the Paraguayan military.” [51:29]

• The Escape:
  “I willed myself to pee my pants ... and just like Alison Mouk, it fucking worked.” [54:05]

• Final Reflection:
  “Any place where you gotta piss yourself to get out of trouble is not a place to find your roots. It’s a place to fucking run from.” [56:40]

Takeaway

Jen’s tale is a surreal odyssey, equal parts comic and harrowing, ending with a lesson about finding belonging where it’s safe—and deploying wild child resourcefulness in apparently hopeless situations.

Notable Outtakes & Closing Reflections

• Kevin on His Mom's DUI:
  “She currently has a list of things that you can do to make this jail cell a more interior design friendly place to boost morale of the drunken inmates. She plans on writing a letter to someone to get it done.” [58:44]
  Even in humiliating legal trouble, Kevin’s mom remains relentlessly herself.

• Episode's Core Message:
  Through extreme embarrassment, these storytellers give voice to secret shame—and model how humor, empathy, or even defiance can turn humiliation into something richer and more human.

Important Segments (With Timestamps)

• [02:25] – Donna Steele’s story of her mother's public bathroom disaster.
• [14:41] – Kevin Allison’s misadventure in hustler bars of NYC.
• [33:29] – Darren Infinity on sex, pride, and the power of words in kink spaces.
• [40:27] – Jen Bosworth’s near-escape from being trafficked in Paraguay.
• [58:44] – Brief coda about Kevin’s mom’s “glamorous” approach to serving jail time.

Tone:
The episode’s tone swings between hilariously unfiltered, vulnerable confessional, and occasionally dark—always with a current of warmth, humanity, and irreverence.

For New Listeners

Whether it’s family secrets, sexual misadventures, or cross-cultural calamity, “How Embarrassing” shows that even the worst moments can become powerful, funny, or even transformational when told with honesty and heart. This episode is especially evocative for anyone who’s ever wondered if they're alone in their shame. Spoiler: You’re not.

[End of Summary]