RISK! Podcast: "How Embarrassing"
Date: January 1, 2026
Host: Kevin Allison
Overview
This episode of RISK! is dedicated to the theme of embarrassmentâthe 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] â [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 Leviâs store dressing roomâforcing Donna to face the ultimate test of daughterly duty.
Memorable Moments & Quotes
-
The Coke Obsession:
âShe could tell the difference between Coca Cola from one McDonaldâs location, like on Parham Road to the other... If it wasnât from McDonaldâs, she would know if you got it from Wendyâs or Burger King, she would flip out, flip out.â [02:42] -
The Unthinkable Happens:
âI see my mother crouching in the corner of the fitting room... And that damn McDonaldâs cup...thereâs shit spray around the cup and thereâs like a little puddle next to it.â [04:08] -
Donna's Refusal:
âMom, I cannot carry your cup of poop through a crowd of 70 people to throw it away.â [05:18] -
Relentless Poise:
âShe walks outside of the Leviâs store and sits on the bench that is right next to the trash can facing the store...walking around Short Pump Mall like she doesnât give a shit.â [09:11] -
Reflection:
âIt amazes me how my mom continuously wants people to think that sheâs all put together and how sheâs able to do it even when sheâs a complete mess.â [12:40]
Takeaway
Despite her momâs mortifying public episodes, Donna ends with an odd sense of respect for her motherâs unflappable image managementâeven amidst total disaster.
2. "Kevin's First (and Last) Attempt at Prostitution" by Kevin Allison
Timestamps: [14:41] â [30:34]
Summary
Kevin shares a comically disastrous memory from his early 20s, stuck in financial limbo and considering his more streetwise roommateâs suggestion: try a little âhustling.â Encouraged by his roommate Rayâs âSeven Laws of Successful Whoring,â Kevin ventures timidly into a hustler barâonly 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:
âI didnât 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.â [14:56] -
Roommateâs Advice:
âSweetie Phone Home ... Money Before Honey ... Hard to Getâs an Easy Bet.â [16:39] -
First Encounter:
âHe 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, âLook at that hair on the back of his hand. That means there's hair on his ass, too.ââ [19:14] -
Disaster in the Cab:
âSo much for money before honey, Donna Summer would have been livid.â [25:08]
ââShut up and put your dick in my mouth.â ... And the driver of the cabâs looking back like, âOh, yeah, hereâs the shut up and put your dick in my mouth moment.ââ [26:54] -
Public Realization:
âI just let it rip. I yell at him, âThe next time you want to suck my cock, you can pay for it first!â And I slammed the door ... two dozen people on Sixth Avenue were staring at me.â [29:15]
Takeaway
Kevin escapes both physical and existential danger, learning that hustling isnât for himâsoon after, he receives news that his comedy groupâs pilot was picked up, a cosmic sign that heâs better off sticking to his true calling (and not pretending to like things he doesnât).
3. "We Could Do a Million Other Things" by Darren Infinity
Timestamps: [33:29] â [40:27]
Summary
Darren recounts a night at a menâs BDSM party where an eagerly anticipated scene with a handsome âdaddyâ 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:
âHe had this very daddy energy to him. Had those laugh lines that told you that heâd walked a few miles but done so with a smile on his face.â [33:52] -
The Turn:
â...he puts his hand on mine and says, âI forgot my pills.â ... and his whole face just showed that he was so upset with himself and with the situation.â [36:53] -
Wish for Better Words:
âI still wish Iâd had the words to tell this beautiful man that it didnât matter that he forgot his pills, that his sexuality was his whole person, not just what was in his pants.â [38:44] -
Lesson Shared:
âThatâs why I teach now ... so that people will have language to tell each other that itâs okay, that sometimes things donât work the way we would like them to work. And that doesnât make us any lesser than.â [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] â [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 motherâs caution and idiosyncrasies, Jen finds herself isolated, broke, and ultimately on the verge of being sold into sexual slaveryâonly escaping by wetting herself, inspired by a childhood classmateâs trick to dodge gym class.
Memorable Quotes & Moments
-
On Not Offending Hosts:
âYou cannot offend the host family ever. They may look different ... may not have as many things as you... Do not offend them.â [41:36] -
Spanish Vocabulary:
âI grew up thinking that everybodyâs mom spoke in Spanish when they were cussing somebody out.â [43:34] -
The Money's Gone:
âMotherfucker, how am I gonna get my motherfuckin cigarettes? Because if youâre a smoker, you know...â [46:24] -
The Sale:
âThis mentor wasnât a mentor. She was a pimp. And it hit me after I came to... Iâm being sold as a prostitute to the Paraguayan military.â [51:29] -
The Escape:
âI willed myself to pee my pants ... and just like Alison Mouk, it fucking worked.â [54:05] -
Final Reflection:
âAny place where you gotta piss yourself to get out of trouble is not a place to find your roots. Itâs a place to fucking run from.â [56:40]
Takeaway
Jenâs tale is a surreal odyssey, equal parts comic and harrowing, ending with a lesson about finding belonging where itâs safeâand deploying wild child resourcefulness in apparently hopeless situations.
Notable Outtakes & Closing Reflections
-
Kevin on His Mom's DUI:
âShe 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.â [58:44]
Even in humiliating legal trouble, Kevinâs mom remains relentlessly herself. -
Episode's Core Message:
Through extreme embarrassment, these storytellers give voice to secret shameâand model how humor, empathy, or even defiance can turn humiliation into something richer and more human.
Important Segments (With Timestamps)
- [02:25] â Donna Steeleâs story of her mother's public bathroom disaster.
- [14:41] â Kevin Allisonâs misadventure in hustler bars of NYC.
- [33:29] â Darren Infinity on sex, pride, and the power of words in kink spaces.
- [40:27] â Jen Bosworthâs near-escape from being trafficked in Paraguay.
- [58:44] â Brief coda about Kevinâs momâs âglamorousâ approach to serving jail time.
Tone:
The episodeâs tone swings between hilariously unfiltered, vulnerable confessional, and occasionally darkâalways with a current of warmth, humanity, and irreverence.
For New Listeners
Whether itâs family secrets, sexual misadventures, or cross-cultural calamity, âHow Embarrassingâ 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 whoâs ever wondered if they're alone in their shame. Spoiler: Youâre not.
[End of Summary]
