The Bert Show – Full Show PT 3: Wednesday, March 25 [Vault]

Date: March 25, 2026
Hosts: Bert, Kristin, Abby, Cassie, Tommy, Jen Hobby, Jeff, Melissa Carter, Wendy
Special Guest: André 3000

Episode Overview

In this engaging episode, the Bert Show crew blends frank talk, relatable humor, and listener participation to tackle a variety of topics including body image positivity, teenage sexting and digital parenting, the ever-challenging dating game, and an insightful interview with hip-hop icon André 3000. The hosts' candid and lively banter brings out both the vulnerability and hilarity of real-life struggles.

Key Discussion Points & Insights

1. Women and Body Image: 'Brag About Yourself!'

(00:40 – 09:50)

Core Discussion

• The hosts revisit a previous discussion that revealed how women often compare specific body parts with each other, usually rooted in personal insecurities.
• The challenge: Can women publicly express pride in a body part without immediately negating it with self-criticism?
• The team goes around the room to "brag" about a body part they love, encouraging listeners to do the same.

Notable Moments & Quotes

• Bird Show Host:
  “Sometimes I feel like when Jeff and I are sitting in here and we’re listening to you women that you are tearing out a page just of the women's playbook and you're giving it to us. And I feel special because I have insight that other guys don't.” (00:40)

• Melissa Carter:
  “Yeah, I don’t like a region of my body, so I naturally just look at other women in that same region because it’s like a comparison… you just kind of gauge yourself based on how other women have that part.” (01:22)

• Jen Hobby (on loving her butt):
  "No, I don't worry about my ass. So I don't look at other people's ass." (03:02)
  Followed by group encouragement to own that pride openly!

• Bird Show Host:
  “You ruined it. You started listing your flaws after being proud!” (04:41)

• Melissa Carter:
  “We would rather be self-deprecating than brag about ourselves.” (04:58)

• Playful banter leads to each team member (and callers) proclaiming their favorite feature:

  • "My name is Wendy, I have beautiful eyes." (05:53)
  • "I am Melissa Carter and my legs will rock your world." (06:04)
  • "My name is Jen Hobby, and I like my ass." (06:19)

• Listeners join the fun, showing confidence:

  • "Hi, I'm Jenny, and I have a delicious spankable butt." (08:11)

Insights

• Discusses the cultural discomfort women have with openly complimenting themselves.
• Highlights societal pressures and gender differences in self-image and self-praise.
• Fun, empowering, and laced with humor and affirmation.

2. Modern Parenting: Sexting, Cell Phones & Trust

(11:54 – 22:47)

Core Discussion

• The hosts delve into the alarming rise of sexting among middle and high schoolers, citing news stories and personal anecdotes from callers and Jen Hobby’s mother (a principal).
• They debate the fine line between parental monitoring and trust, plus the tactics kids use to evade oversight.

Notable Moments & Quotes

• Bird Show Host:
  "If you have a son or daughter in middle school...scroll through their texts and tell us what you find." (11:57)

• Melissa Carter:
  "This is on the heels of that recent survey that said one in five teenagers have sent nude pictures of themselves somewhere." (12:40)

• Jen Hobby (on her mom addressing students):
  “She said, if I collected your cell phones right now, how many of you have something on there you wouldn’t want me to see? And the whole room fell silent.” (13:27)

• Caller stories detail parental controls, discovering explicit content, and confronting behaviors:

  • A mother discovers her 15-year-old daughter's nude photos and the resulting family changes: "I've always trusted her...but that made me realize...things totally have changed in our house." (18:26)
  • Another caller shares discovering her 16-year-old son's texts about smoking pot and drinking, leading to increased restrictions. (22:11)

• Jeff:
  "If my parents had my Facebook or MySpace password, I would just create a different account. Don't you think the majority of kids are doing that?" (17:43)

• Bird Show Host:
  “Nine out of five teenagers and nine out of ten parents think it can’t be their kid.” (22:44)

Insights

• The discussion highlights generational gaps in technology use, the importance of open dialogue between parents and teens, and the reality that both trust and verification are needed in digital parenting.
• The hosts don't shy away from the uncomfortable truths: kids are creative about hiding info, and parental naivety can be risky.

3. André 3000 Interview: Creativity, 'Class of 3000', and OutKast's Future

(24:54 – 33:26)

Core Discussion

• André 3000 discusses the stage adaptation of his Cartoon Network show 'Class of 3000', the value of creativity, and the current (often uncertain) status of OutKast.
• The conversation also covers collaborating with John Legend, his personal creative process, and his views on artistic honesty versus commercial output.

Notable Moments & Quotes

• André 3000 (on creative energy):
  "I have to keep myself excited in a way...I seldom start anything and say, oh man, this would make great money. It’s like, just ideas. You just try them out, and sometimes they work, sometimes they don’t." (26:30)

• Bird Show Host (on OutKast):
  “So you’re saying you’re open to an OutKast album, but there’s always the chance that that’s never going to happen again?” (28:50)

• André 3000:
  “Yeah, it’s always...I might not even put out an album...it all depends on how you feel. When we started it, it was just something we loved to do out of high school.” (28:59)

• On making music:
  “If you look at the OutKast history, we never like just put out two, three albums a year. It was always like, okay, let’s do this album...if you have something to say, that’s why.” (29:24)

• Collaborating with John Legend:
  “The song was done...I was like, oh man, this is something totally different for John...so I put down my little bridge part and...it just turned out to be what it is now.” (30:13)

Memorable Moment

• André clarifies he’s not a natural freestyler, giving props to Big Boi for that skill, and admits to partially freestyling on the John Legend track "Green Light." (31:03)

Insights

• A delightfully candid window into André’s approach to art: fearless, inquisitive, not driven by fame or money.
• He confirms OutKast remains a possibility, but nothing is certain except the love of honest, timely artistic creation.

4. Dating Games: Mojo, Desperation, and Letting Men Hunt

(35:42 – 46:17)

Core Discussion

• Hosts lovingly roast Wendy about her “desperate” approach to dating, dissecting how too much eagerness can sabotage attraction.
• The panel reflects on dating “games” and why playing hard to get (even if it feels unnatural) actually works in the early stages.
• The “Bert takes over Wendy’s dating life” experiment is introduced: Bert will have a phone and communicate with guys on her behalf to demonstrate the art of the “chase.”

Notable Moments & Quotes

• Bird Show Host:
  “You come from a place of desperation and guys can. We can smell it.” (35:58)

• Jeff (on over-preparing for casual events):
  "You come down in a black dress, full makeup, and heels. Like, that is a desperate move right there.” (37:04)

• Melissa Carter:
  “In the dating world, that doesn’t work. You’ve got to play the game.” (38:51)

• Bird Show Host:
  “You don’t let them hunt...you’re a deer that jumps into the back of the truck and goes ‘Here I am.’” (44:51)

• Jen Hobby:
  “Men are hunters. Let them hunt.” (44:47)

• Wendy:
  “I need a urine covered man.” (45:44)

Experiment Roll-Out

• Bird Show Host:
  "When you meet guys this weekend you give them this phone number. They are going to Think they're texting you, but they're really texting me. And I'm going to play it all weekend long. I am going to be you all weekend long." (42:32)

• Jeff:
  “Just let me get them on the boat...you can make them a trophy, you can eat them, whatever, but I’m gonna bring them in.” (44:10)

Insights

• The humor-laden discussion illustrates how mindset and presentation can affect dating success.
• Highlights the challenges of authenticity versus strategy in romantic life, suggesting a middle ground.
• The live experiment promises continued laughs in future episodes.

Timestamps for Key Segments

• Body Image & Self-Bragging Challenge:
  (00:40 – 09:50)
• Teen Sexting & Digital Parenting:
  (11:54 – 22:47)
• André 3000 Interview:
  (24:54 – 33:26)
• Dating Advice & The Mojo Experiment:
  (35:42 – 46:17)

Quotes Hall of Fame

“We would rather be self-deprecating than brag about ourselves.” – Melissa Carter (04:58)

“Men are hunters. Let them hunt.” – Jen Hobby (44:47)

“It’s just ideas. You just try them out, and sometimes they work, sometimes they don’t.” – André 3000 (26:30)

Episode Tone

The episode is lighthearted, warm, and playful but not afraid to expose vulnerabilities or dive into serious conversations. The hosts' authentic camaraderie keeps even the toughest topics feeling approachable.

For New Listeners

This installment captures the full range of the Bert Show’s appeal: sincere connection, humor, pop culture savvy, and heartfelt advice—plus the bonus of André 3000’s wisdom. Whether you want to laugh, learn, or just feel part of a friendly, candid conversation, this is a can’t-miss episode.