The Bert Show – “Vault: Hoss’ Relationship Report Card”

Date: November 24, 2025
Host: Pionaire Podcasting
Cast in Episode: Host D, Hoss, Melissa, Co-host F, Ryan Seacrest, Producer Tracee

Main Theme Overview

This episode puts cast member Hoss in the hot seat with a “Relationship Report Card,” a recurring Bert Show segment. The premise: examine your past relationships to identify patterns, face uncomfortable truths, and encourage personal growth. The team walks Hoss through his limited but intense dating history, poking fun but also providing candid, sometimes awkward, support as he reveals secrets and regrets about his three serious relationships.

Key Discussion Points and Insights

Understanding the “Relationship Report Card” (01:28–02:45)

• Philosophy: Host D explains that the segment is about examining your last 10 relationships (or as many as you have) to diagnose repeating issues. Inspired by advice from askmen.com, the purpose is to foster self-awareness and break toxic cycles.
• Parallel for Listeners: Melissa echoes that many people end up in patterns, fighting or breaking up for the same reasons, and the Report Card helps spot those trends.

Hoss’ Relationship History: A Snapshot (03:06–04:42)

• Limited but Long-Lasting: Hoss admits he’s only dated three women, but all were long-term (1+ years).
• Quick rundown:
  • First: ~1.5 years, high school
  • Second: ~2.5 years, late high school/early college
  • Third: ~3 years, post-college
• Serial Monogamy: Host D and the cast note Hoss’s tendency toward back-to-back serious relationships.
• Notable Moment: The cast jokes about a one-night stand not counting as a relationship.
  • “She was just a, a random on...” – Hoss (03:28)

Patterns and Faithfulness—Uncomfortable Truths (04:52–05:14)

• Hoss Admits Cheating: On the spot, Hoss confesses he’s never been 100% faithful.
  • “0.” – Hoss, in response to being asked how many relationships he was faithful in (05:01)
  • “Screwed around on every girlfriend you’ve ever had, but the ex girlfriend doesn’t know.” – Host D (05:04)
• Cast Reactions: There’s a mix of ribbing and commiseration. Host D admits similar behavior at 24, noting learning from mistakes.

Deep Dive: The Exes, Pseudonyms & The One That Got Away (06:09–11:46)

• The Three Relationships: The cast adopts fake names for anonymity:

  • Virginia: First girlfriend, high school, lost virginity to her.
  • Allison: Second, very slow, platonic relationship; broke up because even holding hands seemed “too fast.”
  • Alicia: Third, longest, most recent.

• Anatomy of the Second Relationship (Virginia/Allison Story):

  • No intimacy beyond holding hands in 2 years; breakup followed Hoss’s attempt to kiss her (08:24–08:55).
  • “She broke up with me because we were moving too fast because I tried to give her a kiss in two years.” – Hoss (08:53)

• Lasting Feelings: Hoss admits he’s harbored feelings for Allison ever since, through other relationships.

  • “Up until right now.” – Hoss, on thinking about her (10:35)

• Missed Connections & The Drunk Email:

  • In college, they reconnect, share a drunken makeout, but ultimately don’t date (11:17–12:17).
  • Hoss eventually sends a "drunk email" to declare his love, not knowing Allison is now engaged to his old friend Brandon (12:30–13:12).

Consequences of Vulnerability—Dealing With the Fallout (13:12–17:40)

• The Engagement Reveal: Hoss finds out only after sending the email—his friend was reading over Allison’s shoulder.

  • “When she opened up the email, he was right over her shoulder.” – Hoss (14:16)

• Regrets & Rationalizations: The group debates whether Brandon was actually there; Melissa is skeptical.

• Closure or Further Complication?

  • Hoss IMs Allison to apologize and ask her to come on the show; she avoids him.
  • “She didn’t IM me back and just signed off right afterwards.” – Hoss (15:54)

• Being Used As “Hand”:

  • The cast discusses whether Allison may be leveraging Hoss’s attention for power in her current relationship.
    • “It gives her, like, the warm, fuzzy feeling...using this email and going, look, what I got, you know?” – Co-host F (16:34)

• Guilt and ‘Man Card’ Surrender:

  • Hoss expresses guilt about breaking friend code but feels relieved to have finally confessed old feelings.

Coming Next—The Report Card Continues (18:24–19:05)

• The first ex, “Virginia,” is scheduled to come on air Wednesday to provide her side, promising more revelations and awkward moments for Hoss.

Notable Quotes & Memorable Moments with Timestamps

• “Screwed around on every girlfriend you’ve ever had, but the ex girlfriend doesn’t know.” – Host D (05:04)

• “I can do stunts. I can act like an idiot…but this right here is just freaking me out.” – Hoss (05:56)

• “She broke up with me because we were moving too fast because I tried to give her a kiss in two years.” – Hoss (08:53)

• “You always want what you can’t touch.” – Ryan Seacrest (09:55)

• “She is sexual Chick-fil-A... When’s the only time you want a waffle cup fry?”
  “Sunday.”
  “But you can’t have it because they close.”**
  – Ryan Seacrest & the Cast (10:10–10:18)

• “I got wasted and decided to send a drunk email…proclaim to her my love for her and how I still think about her all the time.” – Hoss (12:30)

• “When she opened up the email, he was right over her shoulder.” – Hoss (14:16)

• “I should give up my man card right now.” – Hoss (17:23)

Important Segments & Timestamps

• [01:28] – The concept of the Relationship Report Card explained.
• [03:06] – Hoss’s dating history overview.
• [04:52] – Hoss admits to cheating in every serious relationship.
• [07:05] – Deep dive begins: background and pseudonyms for the exes.
• [08:24] – Details of platonic relationship/breakup with Allison.
• [10:10–10:18] – “Sexual Chick-fil-A” analogy.
• [12:30] – The revelation of the drunken love email.
• [13:12] – Learning ex is now engaged to Hoss’s old friend.
• [15:54] – Aftermath: ex avoids Hoss after the confession.
• [16:34] – Discussion on being “used for hand” in a relationship.
• [18:24] – Announcement that Hoss’s first ex “Virginia” will join the show for her report.

Tone & Style

• The Bert Show keeps their tone playful, candid, and irreverent, often blending humor and brutal honesty—sometimes crossing into friendly roasting.
• Hoss is sheepish but sincere, open about embarrassment, and surprisingly honest about his failings.
• The cast balances support and mockery, especially when riffing on Southern roots, “man cards,” and awkward romantic realities.

Summary Takeaway

Listeners are drawn into a raw, entertaining, and at times cringey self-examination as Hoss lays bare his romantic missteps. The episode sets up a week of “Relationship Report Card” segments, with exes returning to share their perspectives—promising even juicier confessions and emotional insights to follow.