Armchair Expert with Dax Shepard

Episode: Armchair Anonymous: Stealing II
Date: December 12, 2025

Overview

This special edition of "Armchair Anonymous" takes listeners on a journey through a range of personal stories about stealing—both accidental and intentional—highlighting the humor, anxiety, growth, and sometimes wild consequences that unfold from these moments. Dax and co-hosts Monica Padman and others invite listeners to share their most memorable "stealing" stories, sparking reflections on human behavior, morality, and the circumstances that turn harmless mischief into major life events.

Key Discussion Points & Insights

Opening Reflections on Stealing (00:18 – 02:46)

• Dax and Monica dive into personal and philosophical takes on the act of stealing.
  • Dax wonders, "What percentage of people get through their whole life without stealing? It's got to be very low, right? Everyone's done a little klepto." (00:34)
  • Monica admits, "I do kind of think shoplifting is cool... particularly age six." (00:47)
• The hosts riff on gender and evolutionary theories of why people steal:
  • Monica: "I think it's still connected to, like, nesting and having things and squirreling away things for the bab." (01:18)
  • Dax jokes about evolutionary roles: "Like me, I have to murder. You know, people come into the village, they want to take the children and the wives who are busy taking, scurrying, stealing." (01:40)

Story 1: Shelly’s Epic Teenage Shoplifting & The Funyuns Bandit (05:49 - 14:49)

Set-up

• Guest: Shelly from Oroville, CA
• Premise: As a teenager, Shelly gets caught stealing a pregnancy test with friends.

Story Highlights

• After moving from the Bay Area, Shelly fell in with a "bad girls" crowd before switching schools and making "good girlfriends."
• When a friend believes she’s pregnant and is grounded, Shelly and crew concoct a plan to steal a pregnancy test from the local grocery.
• Despite an elaborate ruse (including Shelly buying a giant pickle), they're caught via security cameras and taken to the back office.
• The police are summoned. Shelly cheekily insists on paying for her pickle before heading to the station in handcuffs:
  • Shelly: "I decide to tell this cop that's leading me. I go, I haven't paid for my pickle yet." (10:19)
  • Dax: "That's nasty." (10:22)
• Friendly interventions: one parent is horrified; Shelly’s family laughs it off—her brother was just released after robbing a bank with a Funyuns bag.
  • "He went outside and sat on a bench and ordered a pizza and waited for the cops to come and get him. And he spent, like, three years in prison." (13:12)
• Postscript: The pregnancy was real, the “dad” went on to father another child with another group member, and Shelly reflects on her trajectory:
  • "I always say I grew up with the very best bad example, and I went the other way." (13:50)

Notable Quotes

• "Congratulations. That's hard to do." —Monica, praising Shelly for breaking her family’s pattern. (13:55)

Story 2: Jack’s “Greatest Beer Run Ever” (15:20 – 28:21)

Set-up

• Guest: Jack from Hudson Valley, NY
• Premise: A high school adventure leads to stealing an entire beer keg setup from a country club.

Story Highlights

• Jack and his friend Mac, known for pranks and harmless delinquency, break into their former workplace’s snack bar for Swedish Fish.
• They drunkenly escalate—deciding to steal a keg (plus CO2 tank and cooling coils) from a tennis club’s leftover beer tent.
• The loot is set up at Jack’s house for a legendary pool party; mayhem briefly ensues when a beer line bursts open in the sun.
• They were never caught:
  • "Absolutely. Totally got away with it." (26:52)
• Dax reminisces about his own secret bender at Meijer, describing sneaking into the backroom for Jack Daniels after-hours.
• Discussion on the emotional 'cost' of these petty thefts, both literal and psychological.

Notable Quotes

• "We set it up in the backyard by the pool. You feel like kings at this point." —Dax (26:01)
• "You brought back... this is a bad one. But Aaron and I, one time... it was four in the morning, we were out of booze... we just strolled through the cowboy doors into the back warehouse." —Dax recalling his own amends-needing theft. (27:12)

Story 3: Kelly’s Joyride, Juvenile Detention, and International Aftermath (28:56 – 47:48)

Set-up

• Guest: Kelly, now a mom in Tennessee
• Premise: As a troubled 13-year-old, Kelly steals her stepdad's LeBaron, survives a near-catastrophe, and ends up being sent to Venezuela—where her story takes a harrowing international turn.

Story Highlights

• Kelly, low on coping skills and acting out, decides to drive her stepdad’s car for a quick escape to a friend’s house.
• The plan goes awry when a teen boy friend, eager to impress, crashes the car into a neighbor’s retaining wall—just missing the house.
• Kelly is arrested, spends time in juvie, and her family subsequently ships her to live with her father in Venezuela.
• After a brief stint at a missionary boarding school, her father is kidnapped in Colombia and held for ransom for nine months:
  • "They want a million dollars for his release, and they are holding steady to that." (45:14)
• The tale includes bribes at the airport, FBI agents at home, a released father who continues his globe-trotting, and Kelly’s ultimate reflection on gratitude and generational change:
  • "I'm building a software that is directly rooted in an experience with him. He died of frontal temporal dementia... I was just having this moment of immense gratitude..." (47:02)

Notable Quotes

• "We violently jump the curb, go through the front yard, and we hit a decorative retaining wall. And that is what keeps us feet away from going through the front of this stranger's house." —Kelly (40:20)
• "He went outside and sat on a bench and ordered a pizza and waited for the cops to come and get him." —Shelly, about her brother (13:12)

Emotional Resonance

• Dax notes: "There are some 13 year olds dealing with some major shit that adults can't deal with." (48:08)

Story 4: Trish’s Accidental Grand Larceny (49:28 – 58:30)

Set-up

• Guest: Trish from New Jersey
• Premise: While trying to do a good deed by recovering and holding onto a found purse, Trish gets frisked, arrested, and threatened with jail time.

Story Highlights

• Trish sees a purse in a parking lot, assumes it was forgotten, and plans to bring it to police the next day.
• The phone in the purse rings repeatedly (she assumes it's her friend's phone).
• After doing errands, her car is surrounded by police; she’s accused of grand larceny, her phone seized, and is led away in handcuffs:
  • "He looks at me dead in the eye, and he goes, turn around and put your hands behind your back. You're under arrest." (53:33)
• As the investigation drags for months, her reputation and routine are disrupted until the judge dismisses the case—the elderly victim’s son verifies nothing is missing.
• The incident forever colors Trish's instinct to do good deeds:
  • "No good deed if I do and... damned if I don't. No good deed indeed." (57:11)

Notable Quotes

• "He was like, I'm gonna charge you with grand larceny. You could go to prison for, like, 10 years." —Trish, recalling the arresting officer (53:45)
• "You can tell him that he's a jerk off. Yeah, exactly. And then he arrested me for no reason." —Trish’s message to a cop friend, years later (58:02)

Notable Quotes & Memorable Moments

On the Universality of Stealing

• Dax: "What percentage of people get through their whole life without stealing? It's got to be very low, right? Everyone's done a little klepto." (00:34)

On Evolution and Gender Stereotypes

• Monica: "I think it's still connected to, like, nesting and having things and squirreling away things for the bab." (01:18)
• Dax: "Like me, I have to murder. You know, people come into the village, they want to take the children and the wives who are busy taking, scurrying, stealing." (01:41)

On Facing the Consequences

• Shelly: "I always say I grew up with the very best bad example, and I went the other way." (13:50)
• Kelly: "My relief at not going through the house is immediately met by seeing the smoke coming out from the engine and going, there is no way that I'm getting out of this. They're gonna know." (41:00)

On Kindness Gone Wrong

• Trish: "He looks at me dead in the eye, and he goes, turn around and put your hands behind your back. You're under arrest." (53:33)
• Trish's Mom: "When are you going to learn to stop doing these things for people? Like you're going to get arrested again." (57:08)

Timestamps for Key Segments

• Opening banter and reflection on stealing, gender, and morality: 00:18 – 02:46
• Shelly’s pregnancy test shoplifting saga and family history: 05:49 – 14:49
• Jack’s story of the “greatest beer run ever” and nostalgic tales: 15:20 – 28:21
• Kelly’s stolen car, near-miss, juvie, Venezuela, kidnapping, and gratitude: 28:56 – 47:48
• Trish’s attempt at a good deed turns to arrest for grand larceny: 49:28 – 58:30

Tone & Style

The episode strikes a signature "Armchair Expert" blend of warmth, self-deprecating humor, deep empathy, and candid reflection. Dax and his co-hosts laugh but also openly validate the pain, anxiety, and growth in each story. The conversational tone invites listeners to see the humanity in mistakes—and the sometimes wild unintended consequences of even the smallest acts.

Summary Takeaway

The "Stealing II" episode of Armchair Anonymous reveals how ordinary acts of mischief or attempts at helpfulness can spiral into life-changing episodes. Through laughter and empathy, Dax and guests illustrate how our messiest moments sometimes lead to our greatest insights, and how even a stolen keg, LeBaron joyride, or found purse can become turning points in the story of being human.