The Bert Show: Vault – Guys NEVER Do This If You're Trying To Get A Date

Original Air Date: January 13, 2026
Podcast Host: Pionaire Podcasting
Featured Cast: Bert, Kristin, Abby, Cassie, Tommy, Tracy, Maggie, Jen, Phil

Episode Overview

This lively episode dives humorously into the common dating faux pas that men make when trying to impress women. Drawing from real-life observations and personal anecdotes, the cast (with input from Producer Tracy and her friend Maggie) debates which behaviors and fashion choices come off as cheesy, off-putting, or absolute dealbreakers in the dating scene. The result is a comedic but insightful checklist of “never do this” items for guys aiming to improve their chances when out looking for love.

Key Discussion Points & Insights

1. Fashion Faux Pas & Style Missteps

• Visors Worn Upside Down or Backwards

  • "For example, it is never okay to wear a visor upside down. Like, that's just stupid." – Maggie [03:10]
  • Even at beach parties, the consensus is that visors should be worn properly—and attempts to look "rebellious" backfire.

• Cut-Off Sleeves and Baggy Tanks

  • "Cutting off the sleeves of your T-shirt does not mean you have big muscles." – Maggie [03:41]
  • "It comes way down too far where you can kind of see the gut on the side. That's not pretty. It's redneck." – Phil [03:58]
  • The crew agrees that this look is outdated and gives off an undesirable “redneck” vibe.

• Sandals and ‘Mandals’ Debate

  • "Please be very careful with the sandals you choose, because those can go from beachy to dorky really quickly." – Maggie [05:22]
  • "If they have a buckle on them, it's not okay." – Maggie [05:48]
  • "Like flip-flops are okay... But even I have an issue with that. Like if you're wearing sandals, you better be the Lord and Savior." – Jen [05:53]
  • Flip flops get a pass, while sandals with buckles or multiple straps (so-called "mandals") are panned.

• Creative Facial Hair and Sculpted Sideburns

  • "Don't sculpt your sideburns. Like, if you're gonna have sideburns, fine. But if you shape them, like, that's bad." – Maggie [06:38]
  • "That's not a place to get creative with the art." – Jen [07:21]
  • Overly styled or experimental facial hair is deemed unattractive.

• Ill-Fitting Clothes

  • "Wear clothes that fit you like. Is it too much to ask to find a shirt that's not too tight and pants that aren't too baggy?" – Maggie [07:23]
  • Well-fitting attire is universally suggested for better impressions.

2. Cringe-Worthy Behaviors

• The High-Five Approach

  • "It is never okay to give a woman a high five just because she thinks she's hot." – Maggie [04:05]
  • The group laughs at the awkwardness of trying to initiate flirtation with random high-fives.

• Overzealous "Rocking Out" at the Wrong Venues

  • "It is not okay to throw your hands in the air... and rock out to a guy in the corner doing covers of Bryan Adams." – Maggie [04:12]
  • "If you're at an Aussie show, go for it… Otherwise, not hot." – Jen & Phil [04:40–05:08]
  • There’s a line between appropriate enthusiasm and embarrassing expression when it comes to live music.

• Self-Appointed Nicknames

  • "Don't give yourself a nickname. My friend Maggie got hit on by two different guys. One called himself The King, the other called himself G." – Maggie [09:39]
  • Nicknames, especially self-given ones not linked to your actual name, raise red flags and seem forced.

3. Group Dynamics and Social Approaches

• Bringing Female Friends When Going Out

  • "If I were single or my friends who are single, we're not gonna walk up to you, because even though that girl's not yours, she's still gonna judge you." – Maggie [07:44]
  • Having a female friend in your group (who isn’t a date) confuses or intimidates potential female suitors, making them less likely to approach.

• Too Much Group Ambiguity

  • "Is she with him or is she with him? And then there's, like, way too much analysis that has to go into it for you to approach that group." – Phil [08:12]
  • Mixed-gender friend groups make it hard for singles to decipher who is available.

4. Tongue-in-Cheek Self-Awareness

• Several cast members, especially Tracy and Phil, admit to having committed nearly every “cheese offense” on the list at some point—and laugh about it.

  • "After listening to this list, I realized I could go off and put a check mark by every single thing on this list. Everything on this list I have done." – Tracy [08:44]
  • The hosts propose a fun idea: a photo of Phil wearing and doing every “offensive” thing at once, as a cautionary example.

• The cast jokes about entrepreneurial and comic solutions, such as a “female friend focus group” to check your style before heading out, highlighting the cultural anxiety around dating presentation.

  • "Get like a whole group of really cool women together that guys can hire to… tell you what you're doing right and what you're doing wrong." – Tracy [08:21]

Memorable Quotes & Moments

• On Dating Style:

  • "Cheesy is in the eye of the beholder." – Jen [03:07]
  • "If you're wearing sandals, you better be the Lord and Savior." – Jen [05:53]
  • "Don't give yourself a nickname. My friend Maggie got hit on by two different guys. One called himself The King, the other called himself G." – Maggie [09:39]

• On Self-Deprecation:

  • "You are one walking cheese offense. You are G Dog 655." – Tracy [10:15]

• On Group Etiquette:

  • "If you're a single guy and you're going out, like, if there's any girl in your group, girls aren't going to approach you." – Maggie [07:44]

Notable Timestamps

• [03:10] Never wear a visor upside down; don’t try to look like a “bad boy.”
• [03:41] Cut-off sleeves don’t equal big muscles—avoid this “redneck” look.
• [04:05] Awkward high-fiving as a flirt move—don’t.
• [05:22] The dangers of “mandals”: how sandal choices can make or break your look.
• [06:38] Avoid creatively sculpted sideburns and experimental facial hair.
• [07:23] Importance of wearing clothes that actually fit.
• [07:44] Why bringing female friends can be a blockade to meeting new women.
• [09:39] Why self-appointed nicknames (“The King,” “G”) are cringe-worthy.

Conclusion

This episode serves as a lighthearted yet insightful roast of questionable dating practices and style blunders often perpetuated by men. The Bert Show team uses wit, self-deprecation, and real examples to point out all the “cheesy” pitfalls that can ruin a guy’s chances before he ever says hello. If you want to improve your odds in the dating scene or just enjoy a good laugh at the expense of some well-meaning “cheese offenses,” this episode is a must-listen (or, now, a must-read!).