The Bert Show: "Vault: This Guy Refuses To Take the Hint!"

Release Date: December 29, 2025
Podcast by: Pionaire Podcasting

Episode Overview

This episode of The Bert Show centers around a relatable and often frustrating dating dilemma: what happens when someone refuses to acknowledge repeated, subtle rejections and just won't take the hint? The cast and their listeners weigh in with their take on directness, subtlety, and whose responsibility it is to make intentions clear in the world of modern dating. The discussion is sparked by a story from Melissa about her friend—pseudonymously called "Claire"—and a persistent suitor dubbed "Joey."

In classic Bert Show fashion, the team offers humor, honesty, and listener participation, culminating in a collaborative, tongue-in-cheek "Dear Joey" letter to help Claire (and anyone else in her shoes) shut down unwelcome advances with unmistakable clarity.

Key Discussion Points and Insights

1. Setting the Scene – The Persistent Pursuer (01:49–06:45)

• Melissa's Story:
  • Melissa recounts how her friend Claire went on a single lunch date with Joey—set up by a mutual friend. She didn’t feel any connection and politely declined a second date by saying she was unavailable—multiple times—hoping he’d get the hint ([02:20–03:52]).
  • Despite her lack of enthusiasm and increasingly unresponsive behavior, Joey kept calling... including on Thanksgiving, through December, and even on Christmas Day.
  • When Melissa urges Claire to be direct, Claire ultimately calls Joey and gently tells him she’s not interested in pursuing a relationship ([06:30–06:45]).
  • Joey's response: “So what you’re saying is you’re not interested now?”—ignoring the clear rejection ([06:46]).

“She called him and said… ‘I’m just not really interested in a relationship with you.’ And so then his response was, ‘So what you’re saying is you’re not interested now?’”
—Melissa, [06:41–06:46]

2. The Gender Divide on Hints vs. Directness (06:45–12:03)

• The Bert Show crew and callers discuss whether men truly miss subtle signals, or if they choose to ignore them, and whether women are responsible for being more direct.
• Listener Kelly: Advocates for blunt honesty, suggesting Claire should've directly said she didn't feel a spark right after the first date ([07:22]).
• Jeff & Greg (hosts): Counter that some men are genuinely oblivious to hints and need clear verbal communication ([10:00–10:16]).
• Melissa: Pushes back, saying that continual pursuit after months with no reply is on Joey, not Claire, and there’s shared responsibility ([08:12–08:36]).

“If a girl doesn’t call you back for a couple of months, she’s just not that into you.”
—Melissa, [11:11]

3. When Persistence Becomes Problematic (09:00–10:43)

• Caller Amanda: Shares how her father “chased” her mother for months before they got together, advocating that persistence sometimes pays off ([09:00–09:20]).
• The hosts joke about the fine line between “wearing her down” and respectful pursuit, with Melissa and others emphasizing that endless chasing isn’t romantic when someone’s clearly uninterested ([09:25–10:00]).

4. Crafting the "Dear Joey" Letter (12:04–18:36)

• In a humorous, participatory segment, the hosts and listeners collaboratively write a brutally direct rejection letter to Joey, line by line. Their goal: leave zero room for ambiguity.
• Key elements (paraphrased and quoted):
  • “Dear Joey, grasp your ears firmly and remove your head from your ass.” —Host, [13:13]
  • “Your number has already been programmed ‘Do Not Answer’ in my cell phone… do not contact me again.” —Jennifer, [13:25]
  • “I didn’t like you then, I don’t like you now, and I won’t like you in a couple of months from now.” —Yasmine (caller), [14:23]
  • “No means no.” —Nicole (caller), [18:15]
• They debate eliminating even light "compliments," fearing any positive remark might give Joey false hope.

“While your dogged perseverance is flattering, yet a little scary, I am not interested.”
—Drew (caller), critiqued for potentially being too nice, [15:30–15:44]

• For a final flourish, a listener suggests a PS:

“P.S. My jealous ex-boyfriend is getting out of jail. The murder conviction was overturned.”
—Vivian (caller), [18:36]

5. Notable Host Quotes & Moments

• On Male Obviousness:

  “Guys don’t have the conniving gene the way women do.”
  —Jeff, [10:11]

• On Letter Tone:

  “From a guy’s point of view, when you send this letter... don’t put any frills in it. Basic New Times Roman text. Don’t even sign it, just print your name.”
  —Jeff, [16:02–16:28]

• On the Core Message:

  “Here’s to never talking to you again.”
  —Bert, [17:50]

Engaging Moments and Listener Participation

• Caller stories (09:00–10:00): Amanda’s tale of her parents serves as an example that sometimes persistence works—but the hosts push back against romanticizing it when boundaries are ignored.
• Letter Creation (12:04–18:36): The group letter-writing exercise is a highlight, blending humor, exaggerated sincerity, and real talk. Each suggestion is critiqued to ensure there’s no room for misinterpretation or hope.
• Memorable banter: Hosts rib each other about how (un)complicated the male mind is, sparking laughs and keeping the tone light even while tackling a real frustration.

Important Timestamps

• [01:49] - Story introduction: Melissa details Claire's dating dilemma
• [03:52] - Joey’s relentless pursuit outlined
• [06:41] - Claire’s direct call and Joey’s nonplussed response
• [07:22] - First listener call: urge for directness
• [09:00] - Caller Amanda’s persistence story
• [12:04] - Plan for the Dear Joey letter begins
• [13:13] - Iconic opening line for Joey
• [14:23] - Blunt rejection from listener Yasmine
• [18:15] - Nicole ends the letter with “No means no”
• [18:36] - PS from Vivian for comic relief

Conclusion

The episode delivers classic Bert Show energy: honest, funny, and listener-driven. The group grapples with universal questions about modern dating—when to be nice, when to be blunt, and why so many people seem to struggle with (or simply ignore) social cues. The cast’s collaborative “Dear Joey” letter is both cathartic and hilarious, providing a model for how to face uncomfortable conversations with unambiguous honesty.

For anyone who's been on either side of the dating "hints" equation, or just wants a good laugh at the awkwardness of modern romance, this episode is both relatable and delightfully on-brand.