Let's Be Honest with Kristin Cavallari
Episode: My Career In Being The World's Biggest Troublemaker
Release Date: September 2, 2025
Host: Kristin Cavallari (Dear Media)
Episode Overview
In this candid solo episode, Kristin Cavallari dishes out a raw, humorous, and unfiltered account of her rebellious adolescent years. Inspired by her now-teenage children entering pivotal stages of their lives, Kristin reflects on her own journey as a self-described “troublemaker,” recounting formative experiences—her first kiss, sneaking out, shoplifting, and more. Kristin shares how her challenging moments shaped who she is today, offering lessons for fellow parents and a reassuring reminder that even wild teenage years can lead to growth and insight.
Key Discussion Points & Insights
1. Setting the Scene: Family Life & Fall in Nashville
- Kristin opens with updates on her family, especially her son Camden’s obsession with golf (00:02–04:01). She’s enjoying fall in Nashville, her favorite season.
“I'm a golfer now. Breaking news.” (00:03)
2. Parenting & Comparing the Past with the Present
- As Camden enters his teen years, Kristin can’t help but compare his behavior to her own at his age. She expresses pride in Camden's dedication to sports and abstinence from substances, noting that her lack of structured activities as a teen left more space for mischief (00:04–06:46).
“My hobby was getting into trouble. My hobby was drinking and smoking pot and boys. Those were my hobbies. And they kept me very busy, thank you very much.” (00:06:15)
3. Early Years: Fourth-Grade Antics
- Vivid memories from Kristin’s fourth grade:
- Taking her diary to school and getting in trouble for writing a swear word.
- Secretly shaving her legs (and repeatedly cutting herself due to lack of guidance).
- Engages in open discussions about these moments with her own daughter, Sailor (00:07–10:35).
“My teacher, I guess, took my diary at some point and read my fucking diary, which, I'm sorry, should not be allowed.” (00:08:10)
4. Middle School Mayhem: First Kiss & Shift into Trouble
- First kiss in sixth grade—an awkward experience with “Jack” that left her “so repulsed.”
- Notes her tendency for early-developing behavior: “I did everything early. Everything.”
- Eighth grade labeled as the real turning point when Kristin started to truly “get into trouble” (00:11–13:23).
“Jack just shoved his tongue in my mouth... I remember being so repulsed. Like, oh, the first time you have someone else's tongue in your mouth, it's such a weird feeling, right?” (00:12:50)
5. Reflecting on the Roots of Teen Rebellion
- Kristin analyzes her motives: feeling disconnected at home and seeking belonging through risky friendships and bonding over rebellious acts.
- Now embraces her past—no longer ashamed, she believes those choices shaped her identity and values today (00:13:40–15:43).
“The older I've gotten, the more now I have fully embraced my past. I actually think it's a great story. I can laugh at it, and I know that it has shaped me for who I am today.” (00:14:46)
6. Escapades & Consequences: Tales of Eighth Grade
- Cutting Class for Chicago:
- She and best friend Kelsey called each other out of school pretending to be each other’s moms and took the train into downtown Chicago for a shopping excursion (00:22:10–00:25:18).
- Adults discovered their absence, leading to grounding and Kristin’s retaliatory self-pierced cartilage.
“We took the train into Chicago... In our heads, we’re like, harmless, right? This is going to be so fun. Well, as an adult now, like what? Oh my fucking God!” (00:22:40)
- Self-Piercing Antics:
- Pierced her own cartilage and, later, her own belly button—leaving a lifelong scar (00:25:44–00:28:24).
“I pierced my own freaking belly button. Well, really, I sort of had to do it twice... I have the worst scar because I pierced my belly button, like, on top of my belly button.” (00:27:20)
7. Drinking at School & Expulsion Threats (00:28:52–00:33:40)
- Kristin and Kelsey brought airplane bottles of alcohol to school and drank during lunch; got caught after discarding them in a bathroom.
- The same day, she returned to school buzzed for a cheerleading event and was confronted by her coach.
- Faced expulsion but was allowed to withdraw, losing her close group of friends and missing out on key events.
- Attempted to sneak into her banned 8th-grade dance and was immediately discovered.
“We drank them in the bathroom at lunch, and then we put them in the tampon garbage in the stalls. Really smart decision there.” (00:29:20)
8. The Sneaky Years: Sneaking Out & Police Encounters
- Describes how easy it was to sneak out of both her childhood and Laguna Beach homes.
- Shares stories of being brought home by police for breaking curfews or being in the wrong place at the wrong time (00:34:30–00:38:07).
“My mom had just gotten remarried... I just, you know, I was kind of alone... I found connection through my friendships, and I was willing to push it consistently.” (00:15:23)
9. Shoplifting Story & Consequences
- Recalls shoplifting as a high schooler, including (possibly) being banned from Abercrombie at Chicago’s Woodfield Mall.
- One specific incident: attempted to lie about shoplifting to the police—resulting in 100 hours of community service instead of 20, a crucial lesson (00:38:15–00:42:10).
“All of my friends had, like, 15 or 20 hours of community service, and I had 100 for lying. So that, guys, I think, was such a great move on the cop's part...” (00:40:31)
10. Lessons as a Parent: Honesty, Trust, and Staying One Step Ahead
- Kristin now prioritizes honesty in her relationship with her children and encourages parents to foster open communication early (00:43:21–00:47:36).
“Honesty is the most important thing to me. If you’re honest with me, you will not get in trouble.” (00:44:07)
- Shares new-gen teen tricks:
- Kids can "pause" their location on tracking apps like Life360.
- Teens leave their real phone to use burner phones, fooling parents (00:46:40).
“Kids are always one step ahead... You think your kids are over at their friend's house. They're not. They paused their location and they're out having a night on the town.” (00:46:52)
Notable Quotes & Memorable Moments
- “My hobby was getting into trouble. My hobby was drinking and smoking pot and boys. Those were my hobbies.” (00:06:15)
- “Jack just shoved his tongue in my mouth... I remember being so repulsed.” (00:12:50)
- “I pierced my own freaking belly button... Don’t ever pierce your belly button. Take it from me.” (00:27:20)
- “We drank [alcohol] in the bathroom at lunch, and then we put them in the tampon garbage in the stalls. Really smart decision there.” (00:29:20)
- “Kids are always one step ahead... Just something to be aware of.” (00:46:52)
Timestamps of Important Segments
| Timestamp | Segment | |-----------|--------------------------------------------------------------| | 00:02 | Family update, fall in Nashville, Kristin’s new golf hobby | | 00:06 | Kristin compares her childhood to her kids’ adolescence | | 00:08 | Fourth-grade diary & swearing incident | | 00:11 | First kiss and early development anecdotes | | 00:13 | Reflections on connection, shame, and growth | | 00:22 | Eighth grade: cutting class, train to Chicago, self-piercing | | 00:28 | Drinking at school, cheer incident, and expulsion | | 00:34 | Sneaking out adventures & police run-ins | | 00:38 | Shoplifting story, lying, & community service | | 00:43 | Parenting approach: honesty & trust | | 00:46 | Modern teen tricks: Life360 and burner phones |
Tone & Style
Kristin’s tone is confessional, self-deprecating, and often comedic. She is open about her past, neither glamorizing nor shaming her youthful transgressions. The episode is laced with explicit language, humor, and emphasis on personal growth.
Summary for Non-Listeners
If you missed this episode, Kristin Cavallari takes an honest and often hilarious walk down memory lane, confessing her teenage misadventures—from self-administered piercings and underage drinking to sneaking out and shoplifting—and shares how confronting her past has informed her present-day parenting. She also offers hard-won advice: foster trust and open communication with your kids, because, she warns, “They’re always one step ahead.” Fans of real talk and raw storytelling will find this episode a memorable look at how even the wildest teens can grow into self-aware adults.