Vault: Guys NEVER Do This If You're Trying To Get A Date

Summary

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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

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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.

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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  • The crew agrees that this look is outdated and gives off an undesirable “redneck” vibe.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]

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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]

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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.

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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!).

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Transcript

[Announcer]

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[Phil]

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[Tracy]

The Burch show. You know, when it comes to dating and relationships and just being out in the scene, I think in a lot of cases, maybe if you're in the scene, you're too close to it, so you don't have a good perspective on it. There's that word again. But producer Tracy went out over the weekend and she's seeing things while she's out and, and she's in a relationship right now, so she may be seeing things that women and guys aren't seeing because they're just too close to the situation.

[Maggie]

Thank God I am not single anymore because my friend Maggie is so like my assignment lately has been to go out with her and kind of be like her wing woman. And seriously, guys, everybody needs to, every guy needs to take a step back and kind of look at themselves and ask, am I cheesy? Cause 90% of you guys are. It's gotten insane. Like, I went to East Andrews this past weekend and just some of the observations I made there combined with some of the observations I made at our beach party. And we have a lot of good looking guys that come to our events, but a lot of you guys. Come on now.

[Tracy]

Isn't cheesy in the eye of the beholder, though? Like what you might find cheesy, somebody else will find totally hot.

[Jen]

That's the phrase. That's the phrase. Cheesy is in the eye of the beholder.

[Maggie]

For example, it is never okay to wear a visor upside down. Like, that's just stupid. You're right.

[Tracy]

Even at a beach party.

[Maggie]

Well, wear it right side. Like, what's wrong with wearing it normal?

[Jen]

Yeah, because wearing it upside down says I'm a little bit rebellious and I'm kind of a bad boy.

[Maggie]

What about backwards and upside down?

[Tracy]

Well, you gotta shade the back of your neck when you're at night.

[Phil]

You would be.

[Tracy]

Yeah, at a party.

[Jen]

And it's upside down because he's dyslexic.

[Tracy]

I don't know.

[Maggie]

Along the same lines. Cutting off the sleeves of your T shirt does not mean you have big muscles. I, yeah, I never thought that, I never thought that was a good look for a guy to have to cut off sleeves. And then it, the, the, you know.

[Phil]

Once they cut the sleeves off the shirt shows.

[Maggie]

I mean, it's just, it's just so redneck.

[Phil]

It comes way down too far where you can kind of see the gut on the side. That's not pretty. It's redneck.

[Maggie]

It is never okay to give a woman a high five just because she thinks she's hot.

[Phil]

Who high five?

[Tracy]

Where did that happen?

[Maggie]

This happened. This happened. Night. This guy walks out of. This guy walks by my friend Maggie, looks her up and down and then goes like, you know, sticks his hand up in the air like, oh, I look like what I see. So give me a high five. I was like, are you kidding me? It is not okay to throw your hands in the air like this and rock out to a guy in the corner doing covers of Bryan Adams. Like, that's not a good look.

[Phil]

When is it ever a good look to do that?

[Tracy]

The rock out to do kind of.

[Jen]

The split finger thing in a rock. The devil horns are like, you know, if you're at an Aussie show, go for it.

[Announcer]

Right?

[Phil]

And that's it.

[Jen]

If you're at a. I mean, if you're at a hardcore, you know, one of our sister station rock bands. Classic rock, whatever. Go for it.

[Maggie]

But a small venue, regardless of Michael Bolton.

[Tracy]

Yeah. Yeah. It's gotta be, like, you have to be, like, in your 40s and there for lover boy or something to be doing something like that. Head down.

[Maggie]

Yeah. No.

[Phil]

Or you've got to be in high school hanging out the top of a limo for prom. Yeah.

[Maggie]

But then afterwards, he tried to justify it. Like, that's the best song ever written right there, man. Like, dude, you're the only guy, like, rocking out. It's Bryan Adams, and it's not even the real guy.

[Phil]

Yeah. Not hot. That right there, not hot.

[Maggie]

Okay, this goes back to the beach party. Please be very careful with the sandals you choose, because those can go from beachy to dorky really quickly.

[Phil]

Oh, my God.

[Tracy]

Jen and Jeff have said the same thing. Like, I wear sandals every day in work, and it drives them crazy.

[Phil]

No, it doesn't drive me crazy. Cause you kind of got the California thing going on. But a friend of mine will not date a guy who wears mandals. She calls them mandals. Cause they're man sandals.

[Tracy]

These are mandles.

[Maggie]

Here's a really good tip. If they have a buckle on them, it's not okay.

[Phil]

Yeah, a buckle makes it a mandal.

[Jen]

Or I think more than two straps. Like, flip flops are okay. And then maybe if you're gonna do a sandal and you have a basic one, and maybe it goes behind the heel, but even I have an issue with that. Like, if you're wearing sandals, you better be the Lord and Savior.

[Tracy]

You better be walking across the desert.

[Phil]

Sure.

[Jen]

No walking desert, no water. Yes.

[Phil]

Like, I think flip flops. Okay. As long as they are, like, event appropriate. And as long as they aren't, like, 25 years old. Like Michael Checkaways that are basically, like, skinnier than a penny because it's been so long.

[Jen]

He goes to Walmart every season and stacks up on new ones.

[Phil]

All right.

[Maggie]

Don't.

[Announcer]

Dude, no. Shut up. These are J.

[Jen]

Crew, dude.

[Tracy]

Stop talking about me on the radio. I'm never gonna have sex again. No, you are never gonna have sex anyway.

[Jen]

Not the radio, son.

[Maggie]

Don't sculpt your sideburns. Like, if you're gonna have sideburns, fine. But if you shape them, like, that's bad.

[Tracy]

People are still doing that. Like, that whole.

[Phil]

Now, wait, wait. Phil, do this for a while. Where he had, like, the Backstreet Boys chin thing going on. Like, where he had, like, the hair along, like, from the sides of the line. Right.

[Maggie]

To define his jawline.

[Phil]

Yeah, to define the jawline because he was afraid of the little double situation happening.

[Maggie]

Well, I saw two guys that had it, so it almost, like, defined their cheekbone to where, like, it came down like this. And, like, there was, like, a pe. Like, it, like, went all the way to, like, right here.

[Jen]

That's bad.

[Maggie]

Don't shape them. Like, if you're gonna have them, fine. And be really, really careful not to look like Dylan from nine. Like, that's a little too long at that point. Creative facial hair. Not good for a guy.

[Announcer]

Yeah.

[Jen]

That's not a place to get creative with the art.

[Maggie]

Yeah. And 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? Like, that's not a good look.

[Tracy]

Weren't you saying at the Buckhead beach party? Also, this wasn't necessarily a cheese factor, but, like, when guys bring other girls, like, friends with them, like, you're never sure as a girl if you should approach them or not.

[Maggie]

It's not even. You don't know if you should approach them. Like, 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. So, like, if you're a single guy and you're going out with your best friend and his girlfriend, and the three of you are standing there talking, 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 and kind of look at you. So it's just kind of the intimidation factor. So if you're not willing to walk out and talk to other girls, don't just stand there with any other female in your group.

[Phil]

And there's a deciphering factor. Like, okay, which one is she with?

[Jen]

Right.

[Phil]

Right. Like, 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.

[Tracy]

If you want to make a million dollars and you're a woman, it just dawns on me. You know what? Get, like, a. A whole group of really cool women together that guys can hire to come over your house right before you leave to go out and tell you what you're doing right and what you're doing wrong. Dating coaches, a dating coach and go out with you for a couple of hours just to hang with you and tell you what you're doing right and tell you what you're doing wrong.

[Phil]

Uh oh, look at creative facial hair just walked in.

[Tracy]

Hey Jebediah, what's going on? 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 either.

[Maggie]

You'Ve high fived a good looking woman because she's hot.

[Tracy]

Yes, I bought a visor two weeks ago. I'm wearing flip flops today. I am wearing the flip. I'm wearing bad facial hair today. Everything on this list I have done. Or oh, cut off the sleeves on a shirt.

[Phil]

Been there, done it cause he's redneck.

[Tracy]

I thought it would be funny and it kind of backfired on me. It was at the bowling thing that we did. You know what we need to do is we need to put a picture of a fill up on the website doing every offense you just mentioned all at the same time and stick it up there on Friday and say if you're doing any one of these things with like little arrows pointed to all the offenses, then chances are pretty good you're not going to do so great this weekend.

[Maggie]

Can I give you one more and see if Phil does it?

[Tracy]

Yeah.

[Maggie]

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.

[Tracy]

My name's George, but my friends call me G. I think when.

[Jen]

No, see that's. I think that's acceptable.

[Maggie]

No, his name wasn't George. It didn't even start with a G. It was like, I don't know, John or something. But my friends call me G. I.

[Jen]

Think the problem is. Hi, my name's George, but I like to call myself G. You can call me that too.

[Tracy]

The edge. You have yourself a nickname. Oh no, dude. What's my.

[Announcer]

What's.

[Tracy]

Oh, I can't say that, but G Dog, I've gone out and been G dog before. You are one walking cheese offense. You are G dog 655.

[Announcer]

Gotta get kicked in.

[Tracy]

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[Announcer]

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