The Bert Show

Episode: One Bert's Big Adventure Member Has A MAJOR Life Update!
Date: February 19, 2026

Episode Overview

This episode of The Bert Show centers around checking in with former participants of “Bert’s Big Adventure,” the show’s charitable initiative that takes children with chronic and terminal illnesses on all-expenses-paid journeys to Disney World. The main highlight is a major life update from Jennifer, an alum of the trip from 2007, who shares her experience of buying her first home, the challenges she faced, and the importance of independence for children with special needs. The show also revisits the tradition of reading a heartfelt letter from a “Bert’s Big Adventure” mom, reflecting on the impact and community built around these trips.

Key Discussion Points & Insights

1. Reconnecting with Bert’s Big Adventure Alumni

• Host Bert and Kristen discuss the joy, and the “side effect,” of seeing the children from past trips grow into adulthood.
  • Kristen: “You do make us feel old because we picture you on the trip that you were on...That's the only, like, side effect for us is you make us feel like old geezers. But it's still a beautiful thing.” (01:59)

2. Jennifer’s Major Life Update: Buying a House

• Jennifer, alumna from the 2007 trip, joins the show and shares that she has bought her first house, a significant milestone.
  • Host Bert: “So when I heard you were coming on today and you had just bought a house, I'm like, what irresponsible loner gave a seven year old a house?” (02:21)
  • Jennifer: “I just bought a house.” (02:58)
  • She notes that while it’s exciting, it’s also stressful, mainly due to financial responsibilities.
    • Bert: “What's so stressful about it?”
    • Jennifer: “Having to pay for it.” (03:06)
  • Jennifer thoughtfully planned for accessibility, opting for a one-story home because she primarily uses a wheelchair but also walks at times.
    • Kristen: “Was there something special specific you were looking for when you were looking for your first house?”
    • Jennifer: “Yes. I wanted it to be one story...That way I can go around because yes, I can walk. But there's also times we have accidents and you know, I break my arm, break my leg and I need it to be wheelchair accessible.” (03:21)

3. On Resilience, Independence, and Parental Support

• Jennifer shares her experience with independence as a person with special needs.
  • Bert: “So what kind of advice can you give to parents that have kids that are like you to walk that very fine line?”
  • Jennifer: “I know parents want to be there for their kids and help them, but you need to let them learn. It's okay if they fail. That's what makes them stronger. Let them learn that they can do it themselves.” (04:39)

4. Art as a Livelihood

• Jennifer funds her independent life by creating and selling her art.
  • Bert: "So what have you been doing with your life?"
  • Jennifer: "Selling my art." (03:54)
• The hosts remember Jennifer’s artistic talent, referencing a portrait she created in the past for auction.
  • Kristen: “Jennifer does beautiful art because if you remember, she did a portrait of you that was fantastic that we auctioned off.” (03:57)

5. Community and Ongoing Engagement

• Jennifer continues to participate in “Bert’s Big Adventure” events and often brings friends and family—“rolls deep.”
  • Host Bert: “Now we had one mic ready for you, but you were rolling four deep this morning. Sorry. Don't apologize, man. The more the merrier here.” (02:41)

Notable Quotes & Memorable Moments

• On Outgrowing Youthful Stereotypes:

  • Bert: “I have you frozen at like 7 years old. So when I heard you were coming on today and you had just bought a house, I'm like, what irresponsible loner gave a seven-year-old a house?” (02:18)

• On Building Resilience:

  • Jennifer: “Let them learn. It's okay if they fail. That's what makes them stronger.” (04:45)

• Camaraderie & Lighthearted Moments:

  • Bert (teasing about security): "Security, they weren't sure what was going to happen this morning. They're rolling deep with security." (05:04)

Segment Timestamp Guide

| Topic | Timestamps | |----------------------------------------------------|--------------| | Decaf Coffee Mishap & Show Opening | 01:16–01:40 | | Welcoming Jennifer & Her House Purchase | 02:12–03:09 | | Home Accessibility Needs | 03:10–03:34 | | Jennifer’s Art and Income | 03:54–04:16 | | Independence Advice for Parents | 04:16–04:51 | | Fun with Jennifer’s Entourage | 05:01–05:07 | | “Bert’s Big Adventure” Mom Letter Tradition | 05:10–09:03 |

The Annual “Bert’s Big Adventure” Mom Letter

Heartfelt Community Reflection

• Kristen: “Her senior high school graduation photo. But what Holly does every year is she sends a letter to Molly, which Molly ends up sharing with all of us...And we wanted to share with you today what Ms. Hollywood Holly said. Dear BBA family...” (05:17–09:03)

• The letter celebrates the enduring magic and sense of kinship cultivated by the “Bert’s Big Adventure” trips, including touching wishes for volunteers, new families, and the children—reminding everyone of the enduring, joyful community spirit.

  • Kristen (reading Holly's letter): “Our BBA family is cozy and comfortable, even in the most difficult of times. I love you all...May their costumes be clean, pressed and fit like a glove...Find a little BBA magic of your own. We’re praying that this year’s families feel the genuine love you have for them and build the kind of kinship we have with our fellow families from 2012, and that they will feel welcomed in this wacky little family of ours.” (06:57–09:03)

• “It sounded so much more impressive when I said she writes a new letter every year. It's just not true. But we have never let the truth get in the way of a good story on this show.” (Bert, 06:47)

Tone and Style

The episode is lighthearted, authentic, and informal—filled with jokes, banter, and occasional self-deprecation by the hosts, but always conveying warmth and genuine care for the community they’ve built.

Summary

This episode is a touching update on a former “Bert’s Big Adventure” child, now an adult, who shares her achievements and the challenges she’s overcome, highlighting the importance of both parental support and fostering independence in kids with special needs. The segment is wrapped in the show’s characteristic humor and camaraderie, with a moving annual mom’s letter that underscores the ongoing magic and family spirit of the “Bert’s Big Adventure” community.