The Bert Show – Full Show PT 2: Friday, October 31 [Vault]

Original Air Date: October 31, 2025
Host: Bert & The Bert Show Cast (Kristin, Abby, Cassie, Tommy & more)
Notable Guests: Jay Z, Mariah Carey

Episode Overview

This episode weaves together the Bert Show's signature mix of offbeat real-life drama, celebrity interviews, and candid conversations. The highlights include two very raw "second date update" segments in which callers dissect their failed dating experiences on-air; an in-studio appearance by Jay Z reflecting on his career, fame, and origins; and an open, vulnerable chat with Mariah Carey about navigating celebrity and misconceptions. The cast maintains their playful, authentic energy throughout, bringing listeners laughter, perspective, and a front-row seat to moments both awkward and moving.

Key Segments and Timelines

1. Real-Life Dating Drama: “Second Date Update”

[02:15–08:18]

Denise and Matt: Awkward Honesty & Racial Dynamics

• Background: Denise wants to know why her date, Matt, hasn't called her back—though she admits she wasn’t really into him either.
• Matt’s Admission: Matt reveals he’d never dated a black woman before, was “experimenting,” and after the date, decided he “just didn’t like it”.
  • Matt: “I have never been out with a black chick before, and I tried it, and I just didn’t like it. ...It’s not that I’m racist or anything.” (04:11)
• Denise’s Pushback: Denise calls Matt out for treating her as an experiment and suggests he’s afraid to admit he maybe enjoyed it.
• Bert (Host): Pushes Matt to articulate what, exactly, felt so different—Matt can’t answer meaningfully, eventually defaulting to “maybe [Denise] is just a little too aggressive” (06:22).
• Exchange ends: Both agree the date was “far from terrific” and bid each other a curt “how do you do” (08:11).

Notable Moment:

• This segment is a frank, uncomfortable exploration of race, dating, and honesty, with the cast not shying away from calling out problematic attitudes.

2. Interview: Jay Z in the Q100 Studio

[08:18–18:23]

Growing Up in Marcy Projects & Making It Big

• Jay Z’s reflections on Atlanta and his upbringing:
  • "I'm from Marcy Projects. Brooklyn, New York is like, the hood of the hood." (09:33)
  • Describes living in cramped conditions: “It’s like a box. ...So many people on top of each other.” (10:30)
  • Returns to Marcy for a “60 Minutes” piece—now sees his name planted in grass there (11:01).

Success, Fame, and Surreal Moments

• Celebrity Life: Shares about roller skating parties, eating at Waffle House with Beyoncé, and adjusting to the surrealism of fame.
• Vacations & Networking: Describes a lavish holiday with celebrity encounters.
  • “I went to south of France. ...I met Bono over in London. Him and Quincy Jones, they called my room, told me, come downstairs, have drinks.” (12:36)
  • “For the next two weeks, [Bono] was like my concierge service. ...Every day I woke up in a new place.” (13:48)
  • Vivid depiction of extravagant yacht parties and how different “money” looks at certain levels: “Their money is different. ...Boats, 300 foot yachts, homie.” (14:49)

Artistry and Career

• On retiring: The ‘Black Album’ will be his last. “I just want it to be no artwork, just an album. ...If you hear some samba on there, some calypso...anything I want to do, I’m going to just do it.” (11:56)
• On staying motivated: Jay Z’s friends offer tough love; he cites a friend who called “Hard Knock Life” the worst song ever (17:49).
• On recognition as greatest rapper: “I think all rappers believe they the greatest rapper. We arrogant...you need an edge, you know?” (16:10)
• Collaborators on latest album include Lenny Kravitz (17:37).

Notable Quotes:

• “I stayed up the first night I got the boat...drinking wine, like, what am I doing here?” (15:09)
• “You just start to see different levels. Like their money is different...Boats, 300 foot yachts, homie.” (14:49)

3. Second Date Update: Lindsay and KB

[20:49–24:21]

Bar-Hopping to Ghosting

• Story: Lindsay describes a great date with KB, followed by silence for two weeks.
• Confrontation on Air: When asked why he didn’t call back, KB suddenly insults Lindsay, saying, “It would sure be a hell of a lot easier for a girl to get another date if Lindsay wasn’t such a slut.” (22:16)
• The Cast Reacts: The group is shocked; Lindsay denies any wrongdoing—“I have no idea what he means.”
• KB backpedals: Refuses to elaborate.
• Resolution: The show and Lindsay agree KB is “a total idiot,” and praise Lindsay for seeking better (23:58).

Notable Moment:

• This segment highlights the risks of public shaming and the double standard in dating expectations, while offering support to the wronged party.

4. Celebrity Interview: Mariah Carey

[24:23–36:26]

Life as Mariah: Fame, Privacy, and Self-Care

• Arrival & Self-Awareness: Mariah jokes about needing sunglasses due to little sleep: “I’m trying not to be rude and not have ‘em on, but then it’s like the light. I’m like a night creature.” (24:47)
• Daily Life: Shares loving to swim, efforts to sneak in downtime with minimal entourage, and how even quiet moments attract fans: “First person I walk onto the beach, [says] ‘Hey, Mariah, right? Our son's over there. He's in eighth grade. Can he come swim with you?’” (26:16)
• Difficulty Saying No: Admits to always being a “crowd pleaser” and feeling pressure to be accommodating (26:47).
• Always In The Spotlight: Describes the constant cameras, how every action feels amplified, and the need to always be “on,” even during downtime (27:25).

Navigating the Media and Misconceptions

• On being misrepresented: Expresses that even reputable papers published untruths:
  • “I would be reading stuff in credible papers and go…‘This is actually completely fabricated. ...My friends would be there with me, like, ‘You and me were together. This did not occur.’” (31:28)
• On September 11th’s impact in New York: “People became very friendly, like, almost like, ‘Whoa, you know, we are all in this together.’” (29:50)
• On breakdown rumors: “Don’t believe this. Suicide attempts and blah, blah, blah. I’m just not that type of person. ...No matter what, I always go to the positive.” (35:15)

Authenticity and Music as Salvation

• Discusses New Single “Through The Rain”: Written to inspire others and herself, affirming she’s always offered hopeful messages in music.
  • “The point of the song ‘Through the Rain’ is you can make it no matter what happens, if you have faith and truly believe that you can.” (36:16)
• On Living in New York: Reflects on changes post-9/11, her custom-designed apartment, and the pain of losing the Twin Towers from her view (29:15).

Closing Thoughts:

• On misconceptions: “Even we could have this talk and you could be like, ‘Yeah, she was alright.’ …Until you know somebody for a long time, you don’t really know them. ...I’m just grateful I get to sing and write songs and make music.” (34:33)

Memorable Mariah Moments:

• “I let my license expire. ...People in general are better off with me not behind the wheel.” (27:55)
• On tabloids: “You get a lot better ratings saying, ‘Mariah Carey had her 93rd breakdown today…’ than you do saying, ‘Oh, we heard Mariah was out with her friends, smiling and having a nice day.” (30:34)
• “Would you like to inspect my wrist? You can take a magnifying glass. ...You can look back at any of my music and...it’s like, be hopeful, get through it, have faith. That’s what I’m about.” (35:36)

Notable Quotes

• Jay Z: “I think all rappers believe they the greatest rapper. We arrogant...as far as recording. Like, you know, in real life, I'm just a cool, regular person, but when I'm recording...you need an edge, you know?” (16:10)
• Mariah Carey: “You get better ratings saying, ‘Mariah Carey had her 93rd breakdown today...’ than ...‘Mariah was out with her friends, smiling...’” (30:34)
• Bert (on dating honesty): “This is why guys are so confused, right? Here you say you want total honesty, right?” (03:03)
• Denise: “I think you were more afraid that you did like it.” (05:24)

Episode Mood and Takeaways

The Bert Show’s signature warmth, candor, and sometimes-uncomfortable directness set the tone. The chats with Jay Z and Mariah Carey bring depth and humor, touching on the realities and absurdities of massive fame. The dating segments spark real discussion about race, gender, and expectations, with the hosts holding participants (and each other) accountable. Listeners walk away both entertained and challenged to think about authenticity—in relationships, in art, and in public life.

For fans of candid radio, pop culture, and celebrity insight, this episode is a prime example of how The Bert Show’s “real and funny” approach draws out the stories behind the headlines—and the lives behind the microphones.