The Bert Show (Pionaire Podcasting)

Episode: Vault: She's Certain Her Boyfriend Exposed Her On Purpose
Date: December 30, 2025

Episode Overview

In this episode of The Bert Show, the cast tackles a listener’s relationship dilemma centered on a deeply embarrassing and potentially betrayal-laden incident. Ashlyn, the caller, describes how she ended up naked in front of her boyfriend’s roommate—possibly due to her boyfriend’s insistence she didn't need to wear clothes to fetch water, assuring her no one else was home. The episode explores whether this was an innocent miscommunication, an example of immature male humor, or an act of disrespect with sexist undertones. The hosts and callers discuss relationship boundaries, maturity, respect, and the thin line between jokes and humiliation.

Key Discussion Points & Insights

1. Ashlyn’s Incident: What Happened?

• Ashlyn recounts (02:04) that she’s been dating her boyfriend for two months, often staying at his place which he shares with two roommates.
• Late at night, the boyfriend asked her to get water, insisting she didn’t need to get dressed because "nobody's home."
• In the kitchen, she unexpectedly encountered his roommate, Brad, while not wearing any clothes, leading to her mortification.
• When she told her boyfriend, he laughed instead of comforting her, which made her feel even worse.

2. Was it a Set-up?

• The cast explores if the boyfriend orchestrated the event as a "joke" for his roommate’s benefit or if it was just unfortunate timing.
• Crash (regular contributor) expresses doubt it was intentional, citing age (he’s 25, Ashlyn is 24) and not seeing a real incentive:

  "It doesn't sound like something that you would do on purpose. I mean, I wouldn’t want my roommates…" (03:09)

• Contrasting this, some hosts and callers feel the boyfriend’s insistence Ashlyn stay undressed—and his subsequent laughter—could signal intention or, at a minimum, gross insensitivity.

3. Disrespect and Relationship Red Flags

• Jennifer asserts:

  “If it was intentional… it’s disrespectful, because it’s like he was making a mockery of you so that you can be the funny little joke between him and his buddies. I just think that’s totally disrespectful. And that means that he’s not serious about you.” (05:38)

• The hosts probe whether men share intimate or sexual details when not truly serious about a partner, drawing a boundary between 'locker room talk' and genuine respect.

4. Male Humor, Maturity & Double Standards

• Crash and Drewski defend the likelihood of immature, "potty humor" motives:

  “Yeah, I mean, it’s kind of… It’s kind of funny. I mean, if he knew one of his roommates was home and you were completely naked—That’s not funny at all." (04:04)
  “Yeah it is mean. Well, I don’t think he meant like mean-mean. I just thought it’s a guy’s sense of humor. We're, you know, we're like that. …We’re amoebas.” (04:11-04:18)

• The contrast between gender dynamics about discussing partners in private is debated, with women and men accused of similar indiscretions but perhaps for different reasons.

5. How Should Ashlyn Respond?

• The show's advice centers on communication and introspection:
  • Ashlyn should have an honest conversation with her boyfriend about her discomfort and boundaries.
  • If she’s not satisfied with his response or feels ongoing disrespect, it may be time to reconsider the relationship ("At two months, it’s a lot easier to leave than it would be in two years." – Dave, 08:37).
• Dave highlights the importance of maturity and compatibility, noting that reactions in small conflicts are often revealing:

  "People just don't all of a sudden 6 months change into these mature human beings. You're getting a look at him, you know, and his reaction to things like this..." (08:37)

6. Community Call-in & Final Thoughts

• Callers reinforce the central issue as one of respect and how partners respond to each other’s vulnerability and discomfort:
  • Drewski admits at 42 he's "way beyond the potty humor kind of crapola" and wouldn't disrespect a serious partner (10:19).
• There is recognition that Ashlyn may never know for sure if she was set up—but her boyfriend’s reaction and attitude are what really matter moving forward (14:27).

Notable Quotes & Memorable Moments

• Ashlyn (on humiliation):

  “I freaked out, ran back in, ... I don't know if he did that on purpose. I don't know if that's something like guys do... I was so humiliated.” (02:34-02:53)

• Jennifer (on respect):

  “If they plan to be with this woman for a really long time, then they’re not going to talk about their sexual escapades with that woman.” (05:38)

• Crash (on men’s humor):

  “We’re amoebas.” (04:18)
  “It’s almost like potty humor right now.” (07:41)

• Dave (on relationship growth):

  “You’re getting a look at him, you know, and his reaction to things like this...” (08:37)

• Drewski (on maturity):

  "Let me say this. Me, I’m 42 years old, so I’m way beyond the potty humor kind of crapola. And I wouldn’t disrespect my woman like that because...I love her and I’m gonna marry her. That’s me." (10:19)

• Host/Interviewer (on respect):

  “I think that just, it’s so disrespectful and so indecent to do to somebody that you really care about.” (12:43)

• Dave (about the boyfriend's reaction):

  “She’s mostly upset by the fact that he laughed when she came in and she was upset. That’s what she’s upset about.” (12:49)

Important Timestamps

• 02:04: Ashlyn details the incident and sets the scene
• 02:53: Initial reactions and speculation about boyfriend’s motives
• 04:04 – 04:18: Men’s perspectives on humor and intentionality
• 05:38: Jennifer discusses disrespect and seriousness in relationships
• 07:41: “Potty humor” and the maturity debate
• 08:37: Dave’s advice—now is the time to seriously evaluate the relationship
• 10:19: Drewski discusses respect and maturity in relationships
• 12:43: Host underscores the indecency of setting up a partner
• 12:49: Dave highlights the crux—Ashlyn is upset by laughter, not just the incident
• 14:27: The group concludes Ashlyn may never know—but should focus on his reactions

Summary Flow & Tone

The episode is conversational, lively, and unfiltered—hallmarks of The Bert Show’s morning banter. There’s a genuine attempt not to downplay Ashlyn’s feelings, though a comedic, sometimes irreverent tone is present throughout, especially from male hosts (Crash, Drewski). The female hosts and callers anchor the conversation with emphasis on respect and self-worth, encouraging honest confrontation and relationship self-evaluation. The dialogue examines generational and gender disparities in understanding what constitutes a joke versus hurtful disrespect in romantic relationships.

In conclusion:
Ashlyn’s story isn’t just about a naked mishap—it’s a lens into partner respect, boundaries, and how much "humor" is too much. The show doesn’t deliver simple answers but encourages listeners to reflect on relationship standards, the importance of reactions during conflict, and the value of open conversation when boundaries are crossed.