The Bert Show (Pionaire Podcasting)

Vault: Hoss And Rachel

Air Date: November 24, 2025

Episode Overview

This vintage episode of The Bert Show focuses on an honest, often hilarious exploration of past relationships as Hoss gets his "Relationship Report Card" from his ex-girlfriend Rachel. The show delves into their dating history, breakup, and the sometimes uncomfortable but revealing feedback that aims to help Hoss (and listeners) learn and grow in future relationships. The conversation is real, raw, and, classic for the show, full of genuine laughs and candid moments.

Key Discussion Points & Insights

1. Introducing the Relationship Report Card

[02:01–02:48]

• Premise: The Relationship Report Card segment invites an ex-partner to honestly assess what their former significant other did right and wrong, aiming to help them improve in future relationships.
• Purpose: "It's all about you. It's all about, you know, how you were in the relationship." (D, 02:13)
• Host Acknowledgement: Hoss admits to being nervous, and the crew jokes about the vulnerability required for such a segment.

2. Hoss & Rachel’s Relationship Backstory

[02:48–03:31]

• Their Timeline: They dated from junior year of college until recently, with a few on-again, off-again reconciliations.

  "We dated junior year of college through about April of this year. And it's been kind of on and off since." — Hoss ([A], 03:05)

• Breakup Reason: Both were at different points in life, complicated by recent moves.
• Quirky Aside: Running joke about Appalachian State University’s mascot.

  "Go Penguins. You know it? Home of the Penguins. Yeah. Is that really your mascot? No, the Mountaineers, I think." — Hoss & Cast ([A, G], 02:56–03:05)

3. Lighthearted Banter & Anecdotes

[03:31–04:17]

• The team jokes about Hoss’s new neighborhood and a strange man knocking at his door, tying into the show’s signature authentic humor and camaraderie.

4. Rachel’s Candid Feedback: What Hoss Could Improve

[05:11–12:05]

• Immaturity:

  "I think he had an immaturity problem. He's not as mature as I would want somebody to be." — Rachel ([G], 06:04)

• Drinking Habits:

  "He drinks quite often... If there’s a 30-day month, maybe five days out of the week. So, I guess 20 days out of the month." — Rachel ([G], 06:16–06:39)
  Drinking was not a direct source of conflict, but the amount and the differing social priorities raised suspicions.

• Thoughtfulness and Consideration:

  "He could have done like nice, sweeter things sometimes... I never got anything from him — not a note, not a care package. Even when he mailed me my license I left at a bar, it was just an envelope. Not even a note." — Rachel ([G], 08:10–09:03)

• Listening to Needs: Rachel frequently sent Hoss e-cards and messages, but didn’t receive the same effort in return, which made the long-distance nature harder.
• Word Choice: Rachel refers to Hoss as a "boy" versus a "guy," which the hosts playfully pick up on.

5. Areas Where Hoss Got High Marks

[10:10–11:36]

• Emotional Capabilities: Despite calling him immature, Rachel notes Hoss is "funny" and her "best friend."
• Physical Relationship:

  "Oh, God, yes, he's very [good]." — Rachel (about whether Hoss took care of her needs physically, [G], 10:38)
  "Is Hoss a good kisser?" "Oh, yes. Yes, he's a very good kisser." — D & Rachel ([D, G], 10:55–10:58)

• The cast has fun with Hoss’s embarrassment, adding levity:

  "Hoss is now in a fetal position." — D ([D], 10:44) "I'm sucking my thumb." — Hoss ([A], 10:47)

6. Final Feedback and Reflections

[11:36–12:47]

• Patience & Temper:

  "He gets agitated kind of easily with me... I think he just needs to be more patient and be nicer and considerate." — Rachel ([G], 11:36)

• Rachel closes by saying Hoss is fundamentally "a good guy," despite these areas for growth.
• The hosts reinforce the learning spirit of the segment: "The only thing that he heard today was that he's a good kisser and he's good in bed. Everything else is blacked out." ([D, H], 12:05–12:15)
• Hoss reflects on being confused at a new stage in life and expresses warmth for Rachel, despite the unresolved nature of their relationship.

Notable Quotes & Memorable Moments

On Vulnerability

• "I don't like this at all." — Hoss ([A], 02:07)
• "This is what Relationship Report Card does. ... They will brutally be honest with you..." — D ([D], 02:17)

On Critique and Praise

• "He drinks quite often. ... Maybe five days out of the week..." — Rachel ([G], 06:16–06:39)
• "He could have done like nice, sweeter things sometimes." — Rachel ([G], 08:10)
• "Oh, God, yes, he's very [good]." — Rachel ([G], 10:38, re: physical chemistry)
• "The only thing that he heard today was that he's a good kisser and he's good in bed. Everything else is blacked out." — D ([D], 12:05)

Genuine Honesty & Affection

• "He's really funny, and he's my best friend, but ... I just think he might need a little bit more time..." — Rachel ([G], 10:15)
• "She's an awesome girl. I love her to death. And, yeah, like I said, I'm a great kisser. ... You didn't say that — she did." — Hoss ([A], 12:22–12:47)

Structure & Timestamps of Main Segments

| Timestamp | Segment | |------------|------------------------------------------------------------------| | 02:01–02:48| Introduction to Relationship Report Card (& Hoss’s nervousness) | | 02:48–03:31| Hoss & Rachel’s Relationship Backstory | | 03:31–04:17| Banter, Hoss’s new neighborhood, comedic aside | | 05:11–06:13| Rachel begins her feedback — immaturity | | 06:13–09:03| Drinking habits, lack of thoughtfulness, long-distance strain | | 10:10–10:58| Positive feedback: best friend, physical relationship | | 11:36–12:05| Final critique: patience, summary of Hoss as a partner | | 12:05–12:47| Hosts and Hoss reflect, affirm takeaway points |

Tone and Language

True to The Bert Show style, the tone is conversational, irreverent, and affectionate — mixing honesty with comedy. Rachel is forthright but never cruel; Hoss is vulnerable and mostly good-natured, making for a relatable and entertaining listen.

Summary Takeaway

For listeners:
This episode is both funny and insightful, demonstrating the value (and cringe) of honest self-reflection in relationships. The “Relationship Report Card” not only brings out constructive criticism but shows authentic affection and lingering connection between exes — all seasoned with plenty of comedic relief from the Bert Show team.

For Hoss:
Areas for growth: Be more emotionally mature, reduce excessive partying, show tangible thoughtfulness, and practice patience in relationships. But above all — Hoss, you’re apparently a great kisser.