The Bert Show – November 24, 2025 [Vault]

Full Show PT 2
Pionaire Podcasting

Episode Overview

This episode of The Bert Show dives into real-life listener dilemmas and candid, often funny team introspection. The hour centers on a listener named “Julie” grappling with an arranged marriage rooted in her Indian-American background, followed by the team’s “Relationship Report Card” segment, where Hoss faces honest (sometimes brutal) feedback from an ex-girlfriend. As always, the cast—Bert, Kristin, Abby, Cassie, Tommy, and friends—keep things real, raw, and comedic.

1. Arranged Marriage in the Modern U.S.

(Starts at 01:14)

Background:

• Julie (voice disguised, not her real name), 23-year-old daughter of Indian immigrants, shares her experience navigating the pressures of arranged marriage in contemporary America.

Key Discussion Points & Insights:

• Cultural Pressures:

  • Julie’s Indian parents believe that her “prime age” for marriage has arrived after college, and continue to make “suggestions.”
  • Quote: "I've reached that prime age of 23 and get married." – Julie [01:44]

• How Arrangements Happen Today:

  • Parents and family friends introduce possible matches—“suggestions” rather than enforced choices.
  • Julie was not interested initially. Changed her mind when she learned a candidate earned $150-160k/year.
  • Quote: “I’m a little shallow. I’m not afraid to admit that.” – Julie [02:37]

• Exploring Compatibility:

  • She and the candidate share similarities and get along over email/IM, but have never met in person (meeting is planned soon).
  • His lack of relationship or romantic experience (no dating, kissing, drinking, or sex) raises Julie’s concerns & suspicions.
  • Friend (jokingly and problematically) asks him if he’s gay during a chat.

• Red Flags or Cultural Norms?

  • Hosts discuss whether lack of experience = red flag (“rainbow flag” joke) or if it’s just conservative upbringing/prioritizing career.
    • “I don’t necessarily think that’s an indication that he’s gay… For a lot of gay people, they go out with people [of opposite gender] to cover up what they’re doing.” – Show member B [06:15]
  • Julie herself is culturally Indian but personally Americanized, open about partying and having previous relationships.
    • Her plan: When they meet, she’ll come clean about her sexual history in person.

• Audience & Call-Ins:

  • Callers offer varying takes—from “maybe he’s just waiting for an arrangement” to more biting criticism (“gold-digging slut” caller; show pushes back).
    • "She isn't honoring her beliefs if she's a gold-digging slut." – Caller Debbie [12:44]
    • Show member stands up for Julie’s right to be concerned: “I think she’s absolutely in the realm of right, of being concerned that this guy’s never had any interaction whatsoever. I would think that's weird too. I don’t care what culture you’re from.” [13:50]

• Insightful Culture Talk:

  • Another Indian-American caller, Rick, reframes arrange marriage as “parents introducing you to someone”—not all that different from other minority communities or traditional parental pressure in America.

Notable Quotes

• “That red flag doesn't necessarily have to be the rainbow flag.” – [07:15]
• “In their culture, it’s spoken. In other cultures, it’s just understood or implied.” – [12:21]
• On the ‘arranged’ system: “If you meet someone online or whether you meet someone in school or if your parents introduce you to someone, what difference does it make?” – Rick [10:50]

Segment Timestamps

• Arranged Marriage segment begins: 01:14
• Discussion of candidate’s lack of experience: 03:32–07:30
• Cultural commentary and call-ins: 09:29–14:25

2. Relationship Report Card: Hoss Under Fire

(Starts at 16:35, main segment resumes at 16:35 and again at 29:42)

What is “Relationship Report Card?”

• Hoss contacts his ex-girlfriends on-air for feedback, aiming to self-improve and learn why his relationships went wrong.
• “They will brutally be honest with you… tell you what you did right, tell you what you did wrong, and then… you have a little bit better idea how to be better for the next person.” – Host [16:49]

Key Discussion Points:

• Rachel: The Long-term Ex

  • Relationship timeline: Junior year of college through April of this year; on-and-off since; attempted reconciliation.

  • Problems according to Rachel:

    • Immaturity & Heavy Drinking:
      • “He drinks quite often. He goes out a lot… like a lot, a lot…” – Rachel [20:48]
      • Drinks around five days a week; sometimes drinks to excess.
      • Hoss avoided taking Rachel out with friends, creating suspicion about priorities.
    • Lack of Sweet Gestures:
      • “He could have done, like, nice things… I got care packages from his mom, but him, himself—nothing.” – Rachel [22:42]
      • Example: When he overnight-mailed her license, he included no note.
    • Impatience:
      • “He gets agitated kind of easily with me… he just needs to be more patient and be nicer and considerate.” – Rachel [26:08]

  • But…

    • “He’s a really nice guy... a very good kisser.” – Rachel [26:38]
    • Physically attentive and a “best friend,” but still emotionally unready.

  • Takeaways:

    • Immaturity, lack of effort at distance, impatience—not uncommon issues for young men, say hosts.
    • Hoss’s humorous yet defensive reactions: “I’m sucking my thumb.” [25:19] “All he heard today was that he’s a good kisser and he’s good in bed.” [26:44]

• Deeper Dive: Hoss’s Relationship Patterns

  • Hosts encourage examining all past relationships, as people “end up fighting about the same thing… breaking up over the same thing.” [30:33]
  • Hoss reveals limited dating history: Only three serious girlfriends (the show renames them Virginia, Allison, Alicia).
  • Honesty Bomb: Hoss, sometimes not 100% faithful, admits discomfort. (“How many of those three relationships were you completely, 100%... faithful?... This is where I don’t want to talk about it.” [33:41])

• Hoss’s Pining and a Messy Email

  • Reveals regret and lingering feelings (notably for “Allison”).
  • Drunkenly emailed his love to her—unaware she’s engaged to a (former) friend.
  • Email is discovered by fiancé (possibly intentionally shown) and awkward fall-out ensues; “She IMed me saying it was the sweetest thing she ever got.” [46:00]
  • Show notes the power of unresolved feelings and suggests she may be “using Hoss as hand in her relationship” [44:48].

• Hosts’ Analysis

  • Open, honest group reflection; not shying away from uncomfortable truths or painful introspection.
  • Segment is equal parts therapy, comedy, and catharsis.

Notable Quotes

• “When I was 24 years old, there weren’t too many relationships I had where I wasn’t screwing around. I’m not proud of it, but…” – Host [34:23]
• “You always want what you can’t touch. That might be it.” – Hoss reflecting on an ex [38:24]

Timestamps for Key Segments

• Relationship Report Card setup: 16:35
• Rachel’s Feedback (“the Exes”): 17:20–27:00
• Hoss’s Relationship History & Patterns: 29:42–34:00
• Hoss’s “Drunk Email” Saga: 35:00–47:00

3. Memorable & Funny Moments

• Cultural Humor:

  • “That red flag doesn’t necessarily have to be the rainbow flag.” [07:15]

• Honest Admission:

  • Julie’s clear-eyed self-description: “I’m a little shallow. I’m not afraid to admit that.” [02:37]

• Report Card Awkwardness:

  • “I’m sucking my thumb.” – Hoss [25:19]
  • “All he heard today was that he’s a good kisser and he’s good in bed.” [26:44]

• Show Humor:

  • “She is sexual Chick Fil A… When’s the only time you want a waffle cup fry? Sunday afternoon when they’re not open. But you can’t have it… that’s all you wanted.” – Hoss/Hosts riff on the allure of the unavailable [38:47]

4. Conclusion & Episode Flow

This episode offers an honest look at culture, dating, and the messiness of young adulthood. Julie’s story provokes real debate about arranged marriage—its modern forms, immigrant American identity, and generational values. Hoss’s “Report Card” provides raw, revealing relationship lessons, showing the power (and pain/fun) of self-examination. Add in witty banter, punchy moments, and open calls, and it’s an episode that feels both universally relatable and intensely personal.

For Listeners:

If you want to hear:

• Candid takes on arranged marriages in the U.S. (from multiple generational and cultural perspectives)
• Brutally honest relationship self-examination
• A balance of empathy, humor, and “keeping it real”

Don’t miss:

• Julie’s first-person arranged marriage story (01:15–14:25)
• Rachel’s on-air relationship “report card” for Hoss (17:20–27:00)
• Hoss’s confessions and the “drunk email” saga (35:00–47:00)

This summary skips advertisements and non-content banter to focus on the show’s most substantial themes and discussions.