RISK!

Latest Episodes:

Create My Life Jan 13, 2026

Show notes

Ms. Aishia tells Cyndi Freeman about the time she navigated a complex, emotionally abusive relationship, and ultimately found the strength to prioritize her own happiness and independence. You can also watch this episode on YouTube.

Check out all of our Conversation Stories!

Conversation Story: Create My Life by Ms. Aishia

EDITOR’S SYNOPSIS: After leaving an abusive relationship, Ms. Aishia enters an intense, largely virtual romance that slowly destabilizes her sense of self, leading her to sever ties, confront emotional dependency, and ultimately rebuild her life through radical change and solo travel.

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The Best of Funny Stuff #7 Jan 08, 2026

Show notes

There’s nothing but laughs in our Funny Stuff compilations of classic RISK! stories on the lighter side. This week, Kumail Nanjiani and Alecia Altstaetter share about penile injuries and barf boats.

🎤Live Story: Pure Fuckmachine by Kumail Nanjiani

Kumail learns how to masturbate and is so excited that he zips his pants too quickly afterward and cuts his penis on the zipper.

🎤Live Story: That New Ship Smell by Alecia Altstaetter

Alecia and her husband decide to take the kids on the high speed car ferry across Lake Michigan. A huge storm breaks out. The family ends up in the hospital covered in blood, urine, vomit and lake water by the end of the fiasco.

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• 🎟 See RISK! live⁠ in NYC on Tuesday, March 17, 2026

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Holiday Blues #3 Jan 06, 2026

Show notes

Michael J Bennett and Jessica Piscitelli Robinson tell holiday stories that are new, true and kinda blue.

🎙️Radio Story: Santa's Revenge by Michael J Bennett

Michael is a shopping mall Santa when his worst teacher from High School comes in with his kid. The rule of a store Santa is make no big promises the parents have to fulfill. Michael promises this kid the moon and a pony.

🎙️Radio Story: A Mom-Made Christmas by Jessica Piscitelli Robinson

Jessica is a teen when her mom has a stroke right before Christmas. Her mom was the end all be all of making Christmas magical throughout Jessica’s life. But this holiday, the miracle was simply being able to bring mom home on Christmas Day.

🌈 Support RISK! & Get Involved

• 🎟 See RISK! live⁠ at Caveat in NYC on March 17, 2026

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In 2026, Jump In On RISK! Jan 05, 2026

Show notes

Kevin announces RISK!’s goal this year -- helping listeners connect. More social events, more online fun, and Kevin’s latest online storytelling workshops. One starts on Jan 14, one on Feb 15. Email kevin@risk-show.com to jump on in!

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How Embarrassing Jan 01, 2026

Show notes

A Classic RISK! episode from our early years that first ran in September of 2013, when Kevin Allison, Jen Bosworth, Donna Steele and Dare Campbell all shared stories of humiliation.

🎤Radio Story: Mother’s Little Helper by Donna Steele

(Content note: poop) Donna’s mother has a strange habit of pooping in public. On this occasion, it’s into a McDonald’s coke cup in a mall dressing room. Donna is in awe of her mom’s nonchalance.

🎤Live Story: The Hustler by Kevin Allison

In his early 20s, Kevin goes to a hustler bar to try to raise money for that month's rent. But despite following a friend's "7 Laws of Successful Whoring," his first attempt is a comedy of errors.

🎤Radio Story: We Could Do a Million Other Things by Dare Campbell

A BDSM date with a stranger abruptly derails when Dare’s partner forgets erectile-dysfunction medication, and flees. Dare learns to assure partners that sexual performance is unnecessary. There’s many ways to have erotic fun.

🎤Live Story: Job Satisfaction in Paraguay? by Jen Bosworth-Ramirez

Jen’s mother suggests she take a journey to Paraguay. There, Jen is robbed and then nearly sold into sex slavery, but she fakes insanity by peeing all over herself and gets away.

🌈 Support RISK! & Get Involved

• 🎟 See RISK! live⁠ on March 17 in NYC

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Hosts with the Mosts Dec 30, 2025

Show notes

JC Cassis, David Crabb and Cyndi Freeman share stories at RISK! live shows when they were hosting

🎤Live Story: Not That Casual by JC Cassis

As a young woman, JC is excited to go to a wild NYE party. A hot guy dances with her as if he's a middle school boy. She says he can be more casual. He takes out his dick and grinds on her. She tells him “Not THAT casual.”

🎤Live Story: Kitchen Nightmares! by David Crabb

After moving to LA, David invites new friends to try one of the few restaurants in his neighborhood open late, only to discover they’ve wandered into a real-life Kitchen Nightmares episode, the most chaotic restaurant ever.

🎤Livestream Story: Tipping Points by Cyndi Freeman

Cyndi's new boyfriend seems to be a dream boat. Jealous over her getting a big tip at her new bar job, his misogyny shows. Cyndi decides to dump him, whereas in the past, she had stayed too long with toxic people.

🌈 Support RISK! & Get Involved

• 🎟 See RISK! live⁠ on March 17, 2026 in NYC

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Holiday Stories Fan Favorites! Dec 25, 2025

Show notes

Every holiday season, RISK! fans ask about this small handful of yuletide perennial favorites. Well here they all are, wrapped up in one neat package with a bow. Unwrap and enjoy these stories from Elna Baker, Kevin Allison, Sarah Long Hendershot, and Kate Bohl.

🎤Live Story: For the Love of Nubbins by Elna Baker

Selling expensive, real-looking baby dolls for the holiday season at FAO Schwartz, Elna “adopts” an unpopular one she calls Nubbins, a Black babydoll. When the doll is bought, Elna grieves.

🎤Radio Story: The Allison Family Christmas Tree by Kevin Allison

Inspired by a Charlie Brown Christmas, Kevin’s dad begins a Christmas Tree procuring tradition in the early 70s that gets more complex and includes more people each year, featuring long distance travel, the Catholic Mass, and dirty diapers.

🎤Radio Story: The Present by Sarah Long Hendershot

During a brutally cold winter, Sarah was a single mother with an 11-year old son, but she was out of work and on the verge of going homeless. Then a present arrived. A box filled with money. It was a fellow musician who suspected she might need it.

🎤Radio Story: Snowglobe by Kate (neé Kevin) Bohl

Kate (at the time, Kevin) is locking up her bar as a blizzard begins. A beautiful young woman begs to come in for a moment to gather her bearings before figuring out how to get home. They slow dance to Billie Holiday

🌈 Support RISK! & Get Involved

• 🎟 See RISK! live⁠ in NYC on March 17, 2026

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• 📚 Shop merch or the RISK! book⁠

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• 🎥 Hire Kevin as a coach or get personalized videos

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Holiday Stories #18 Dec 23, 2025

Show notes

Ty Gentile, James Rana, and David Hu share yuletide tales about Christmas carols, unorthodox Santas, and of course, excretory health in our annual winter holidays special for 2025.

🎙️Radio Story: A Very Moving Christmas by David Hu

David’s dad has Alzheimer’s. David always struggled to understand how to give and receive love from his immigrant father. But when he buys his dad dearly needed laxatives for Xmas, it’s a touching moment of bonding.

🎙️Radio Story: The Widow’s Song by Ty Gentile

Struggling with homesickness, Ty gets a gig working as a Christmas elf in costume. He is surprised to find himself crying when an old widow breaks the tension in the crowd by breaking into song singing a Christmas carol.

🎙️Radio Story: Alternative Santa by James Rana

James gets a gig as a Santa and, in spite of being dark-skinned with a Muslim surname, he takes it and likes it. Then he’s asked to do a party for Kellyanne Conway (of the Trump administration) and is conflicted.

🌈 Support RISK! & Get Involved

🎟 See RISK! live⁠ in NYC on March 17, 2026

✍️ Pitch your story⁠

❤️ Support us on Patreon⁠ or ⁠make a one-time PayPal donation⁠

📚 Shop merch or the RISK! book⁠

🎓 Take storytelling classes with us⁠
🎥 Hire Kevin as a coach or get personalized videos

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Holiday Stories #4 Dec 18, 2025

Show notes

A Classic RISK! episode from our early years that first ran in December of 2013, when Alex Edelman, Jude Treder-Wolff and Danielle Kramer all shared Yuletide tales.

🎤Live Story: Oy to the World by Alex Edelman

In the story that eventually became his Broadway show and HBO special “Just For Us,” Alex shares how, in his childhood, his Orthodox Jewish family hosting Christmas to comfort a lonely friend led to life lessons.

🎤Radio Story: Winter Storm by Jude Treder-Wolff

Driving home for Christmas in a massive blizzard, Jude and her sister get into a huge fight in the car. Jude is going to reveal to the family that she’s leaving the country for a while and everyone is upset about it.

🎤Live Story: To Kids from 1 to 92 by Danielle Kramer

A rebellious teen, Danielle despises Christmas, but after moving away and experiencing the loss of her grandfather and father, she comes to cherish family traditions, realizing the love her parents put into the holidays.

🌈 Support RISK! & Get Involved

• 🎟 See RISK! live⁠ in NYC on March 17, 2026

• ✍️ Pitch your story⁠

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• 📚 Shop merch or the RISK! book⁠
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Sex & Supper Dec 16, 2025

Show notes

Nikki Bailey and Hana Nobel share stories about how messy things can get with food and sex, with guest host, Taj Easton.

🎤Live Story: That's Not Sexy, Baby by Nikki Bailey

For Nikki, her hookup’s praise of her body is a boost to her self esteem. But when her digestive system acts up, she must become downright defiant about self-acceptance.

keywords: Plus Sized Dating, Self-Acceptance, Queer, Body Positivity, BoPo, Self-Worth, Body Acceptance, Empowerment, Mr. Big, Sex and the City, Farting, Fuckboys, Hookup, U Up?, LGBTQ+

🎤Live Story: Curry Coitus by Hana Nobel

After returning from a week of mourning, Hana tries to revive the night with a sexy food-play surprise involving Indian takeout. It triggers a rash, and an unexpectedly grounding moment in her early relationship.

keywords: food play, Sex and the City, Samantha Jones, Indian Food, Curry, Shiva, New Boyfriend, Burning Man, Ringworm, unexpected rash, sex positivity, mourning, grief, stages of grief

🌈 Support RISK! & Get Involved

• 🎟 See RISK! live!

• ✍️ Pitch your story⁠

• ❤️ Support us on Patreon⁠ or ⁠make a one-time PayPal donation⁠

• 📚 Shop merch or the RISK! book⁠

• 🎓 Take storytelling classes with us⁠
• 🎥 Hire Kevin as a coach or get personalized videos

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