Vault: He needs help approaching women

Summary

The Bert Show: Vault – He Needs Help Approaching Women

Date: June 17, 2026
Main Guests: Bert (Host), Intern Brandon, Jen, Yvette, “Wingman/Coach” Dolvett, Callers

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Episode Overview

This episode of The Bert Show centers around intern Brandon, a young man who admits to having little experience with dating and approaching women. The cast and guest “wingman/coach” Dolvett band together to offer Brandon advice, encouragement, and practical steps to improve his confidence and skills in social interactions with women. The conversation is light-hearted, supportive, and full of humor, with input from both the cast and audience members.

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Key Discussion Points & Insights

Brandon’s Story and Challenges

• Background: Brandon, age 21, has only had one serious girlfriend in high school and hasn’t dated much since, primarily due to focusing on baseball. (02:00)
• Limited Experience: He openly admits he’s never approached a woman in a bar or club and is unsure how to even start a conversation. (04:03)
• Self-Awareness: Brandon often helps his friends with advice but struggles to apply it himself, describing a kind of “watch, but not act” mentality. (03:04)

Panel Reactions and Advice

Step-by-Step Guidance

• Introduce Yourself:
  Jen: "First thing you say, just introduce yourself. Say, hi, I’m Brandon. Just say your name. That way it automatically... you’ve identified yourself." (09:05)

• Confidence Comes from Within:
  Dolvett: "I think it comes from inside. I think confidence, regardless of what’s on the outside... it’s from the inside out is where confidence comes from." (05:58)

• Be Yourself:
  Yvette: "Don’t try so hard when it comes to—I have to—you know, just be yourself. You have all the tools, obviously." (10:22)

Practice and Perspective

• Switching Mindset:
  Brandon shares that he’s confident at events because “most of these people I’ll never see again, so what do I care what they think about me?” The cast encourages him to apply that mindset at bars. (10:32)
• Coaching by Experience:
  The plan is for Brandon to go out with Dolvett (the “Mr. Miyagi” of dating confidence), so he’ll be "forced" into conversations in a supportive, real-world setting. (04:44, 11:46)
• “Leftovers” Practice:
  Host jokes about how if Dolvett attracts a crowd, Brandon can gain practice by talking to women who approach their group but aren’t interested in Dolvett. (12:17)

Looks vs. Confidence

• Do Good Looks Equal Good Game?
  Panel debates whether good-looking people naturally have more confidence. Yvette and Jen note that looks help get attention, but true confidence is magnetic and comes from within. (06:09, 06:38)
• Callers’ Perspective:
  A listener, Edward, emphasizes how looks can make things easier but agrees with Jen that confidence is often more important:
  "You make me believe what you believe in based on what comes out of your spirit." (13:59)

Practical Role-Playing and Humor

• Mock Approaches:
  Brandon, prodded by the group, awkwardly practices on Jen and Wendy, met with laughter. They encourage him not to overthink it and keep things simple. (08:01–08:45)

• Bert’s Admission:
  Bert confesses he used to make up fake names at bars because he was self-conscious about "Bert." (09:31)

• Memorable Quotes:

  • Wingman/Coach: "You just gotta practice it." (11:30)
  • Ricky (Listener): "Cocky, sensitive, and funny—you get those three things in the first 15 minutes, she’s yours." (11:02)
  • Yvette: "You never lose because you have nothing to lose." (10:55)

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Notable Quotes & Memorable Moments

• “I check my shirt to make sure I don’t have a stain on it, because that’s probably why she’s looking at me.”
  — Brandon (03:36)

• “All eyes on Dolvett. He just has an attitude and a charisma and he’s a good-looking guy.”
  — Bert (05:10)

• “Don’t try so hard... just be yourself.”
  — Jen (10:22)

• "You just gotta practice it."
  — Wingman/Coach (11:30)

• "He's like BP [batting practice] with the Braves."
  — Brandon (15:42; comparing his upcoming "training" with Dolvett to sports practice)

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Important Timestamps

• [02:00] – Brandon explains his lack of dating experience.
• [03:29] – Theoretical scenario: what does Brandon do if a woman gives him “the look?”
• [04:17] – Brandon admits needing "the pocket manual" for dating.
• [05:10] – Discussion about Dolvett’s charisma and confidence.
• [06:09] – Panelists discuss the source of confidence: looks or personality?
• [09:05] – Jen gives concrete advice: just introduce yourself by name.
• [10:22] – Yvette and Jen encourage Brandon to be himself and not try too hard.
• [11:02] – Ricky calls in with his advice on being "cocky, sensitive, and funny."
• [11:46] – Plan revealed: Brandon will be coached out in the field by Dolvett.
• [13:52] – Debate about the importance of looks versus confidence.
• [15:42] – Sports/dating analogy as Brandon prepares for real-world practice with the team.

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Episode Wrap-Up

The show wraps with plans to help Brandon get real-life social "reps" by going out with more experienced friends, learning through practice—not overthinking, but simply building his confidence muscle. The cast is supportive, the mood playful, and the advice both practical and encouraging: be authentic, introduce yourself with confidence, and remember—everyone is working on something.

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The Bert Show cast reminds listeners that being real, vulnerable, and willing to learn is a strength—and that even the most daunting social skills can be developed with the right support and a bit of practice.

Transcript

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[Brandon (Intern)]

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[Host/Interviewer]

Hey, the bird show. Right now we are gonna focus on our intern, Brandon. Now, have you turned 21 yet or

[Brandon (Intern)]

you are turning 20? I turned 21 last June.

[Host/Interviewer]

You did? And you're a guy that doesn't drink much?

[Brandon (Intern)]

No. One night I had way too many Jager bombs not drinking that much ever.

[Host/Interviewer]

And it just took one night for

[Brandon (Intern)]

you to realize it took one night?

[Wingman/Coach]

Yeah, that's it.

[Brandon (Intern)]

Yeah.

[Host/Interviewer]

I wish I'd learned that lesson when I was 21, dude. And Brandon told us that off the air that, you know, he just doesn't have a whole bunch of experience when it comes to women.

[Brandon (Intern)]

Yeah, yeah. You know, I played baseball for most of my life, so that's been my love you know, that's what I focus on all growing up. So while most of my friends were out chasing women, I was playing baseball.

[Female Commentator]

Have you ever had serious girlfriends or dated a lot?

[Brandon (Intern)]

Yeah, I had one serious girlfriend senior year of high school. But before that it was just like normal school relationships, you know, nothing serious.

[Wingman/Coach]

Where you hold hands and you're quote unquote going out.

[Brandon (Intern)]

Yeah, like the check box. Do you like me? Yes. No.

[SpinQuest Promoter (Female)]

Maybe.

[Brandon (Intern)]

You never put the maybe on there because that looks great. Or you have your friend go up and ask her and be like, hey, do you like him? That kind of stuff. In eighth grade, ninth grade.

[Host/Interviewer]

That's cool when you're 12, but not so much when you're 21.

[Brandon (Intern)]

Well, when you're a junior in high school too, Right? I'm just saying.

[Host/Interviewer]

So now from high school to now, how many women have you dated?

[Jen (Female Commentator)]

One.

[Host/Interviewer]

One? Yeah. Long term relationship years.

[Brandon (Intern)]

Yeah. And I didn't ask her to move in and fear that she was going to live with some guy. Yeah, you know.

[Host/Interviewer]

So have you gone on many dates but just not relationships or is it pretty much just that one girl and that's it?

[Brandon (Intern)]

Well, yeah, pretty much that one girl and that was it. You know, like all my friends come to me for advice because I'm more of the type to sit back and watch our other people react and then be able to help with that. But rather than implementing it myself, I can't do that. So.

[Host/Interviewer]

So what happens normally? Let's say we are at Havana Club now, right? And you're in the lounge by yourself or with a couple of dudes and there's a hottie across the bar.

[Caller/Listener]

Okay.

[Host/Interviewer]

And she sort of gives you that.

[Brandon (Intern)]

The look.

[Host/Interviewer]

Just the look, you know, it's just.

[Wingman/Coach]

She flips her hair a little bit.

[Host/Interviewer]

It's the look. What do you do?

[Brandon (Intern)]

I check my shirt to make sure I don't have a stain on it because that's probably why she's looking at me. What is he wearing? You know, I'm checking him like. So lie on the wall. No.

[Host/Interviewer]

Are you confident? Do you want my friend? Is it my friend you're looking at?

[Brandon (Intern)]

No, I'm not. I don't me.

[Spanish Commercial Announcer]

Him.

[Female Commentator]

Him?

[Brandon (Intern)]

Yeah, it's like him pointing back and forth. I don't know.

[Host/Interviewer]

You must have some kind of experience like approaching a woman in a bar though.

[Brandon (Intern)]

No, none.

[Wingman/Coach]

Never? You've never just walked up to a girl and tried to start a conversation?

[Brandon (Intern)]

No, I never pulled the hey, how you doing? You know any of that? No.

[Wingman/Coach]

Okay, step by Step help on how to do that.

[Brandon (Intern)]

Basically, I need, like, the Pocket Manual.

[Host/Interviewer]

Okay, well, I'm glad you said that because I think we have him here today.

[Wingman/Coach]

Yeah, that's his name actually on Twitter.

[Brandon (Intern)]

Pocketmanual Dating.

[Wingman/Coach]

Pocket Manual.

[Host/Interviewer]

This is one of my best friends, Dolvett, here, and we are in very different parts of our life right now. But if I was a single guy, this is the dude right here that I want as my wingman every night that I go out.

[Wingman/Coach]

He's your Mr. Miyagi.

[Host/Interviewer]

He should be right here, man. So really our hope today, Dolvett, was that Brandon here in a weekend coming up, could just sort of hang with us when we go out one weekend. Mostly. You, us, us. Well, we'll all go out and get our drink on and stuff. But, I mean, you are. You're gonna be his Mr. Miyagi.

[Caller/Listener]

Okay.

[Jen (Female Commentator)]

Daniel's son, Danielson wax on.

[Host/Interviewer]

Wax on. But I was trying to think, like yesterday we started talking about this and let me pose this to the women in the room again. And I'm not exactly sure how to phrase it. Like, I've seen you in clubs and I've seen you in bars when Dolvette walks into a place. This is one of the things about Dolvett that I really admire. Like, all eyes on Dolvett. He just has an attitude and a charisma and he's a good looking guy.

[Jen (Female Commentator)]

So I paid him so much money

[Brandon (Intern)]

to say that, I swear to God,

[Host/Interviewer]

it's all eyes on Dolve.

[SpinQuest Promoter]

All right.

[Host/Interviewer]

We joke that if we go out in Atlanta, I'm Vince from Entourage, but if we go out anywhere else, all eyes are on Dolvett and I don't get any attention at all all night long.

[Wingman/Coach]

Well, he's a confident guy.

[Host/Interviewer]

Well, this is what I want to ask. Like, does the confidence, does the game and the confidence come because he's a good looking guy, or would he. Would he have that if he was an average looking dude?

[Wingman/Coach]

I think it comes from inside. I think confidence, regardless of what's on the outside. I mean, Dolvett is a really good looking guy and he takes good care of himself. But. But I think it's from the inside out is where confidence comes from.

[Yvette (Female Commentator)]

I think good looking people have an edge. I do agree with Jen. I do think average looking people probably have to build that a little more than good looking people. I think naturally good looking people, they get a point, have an edge. They have an edge because they get attention even without doing Anything. I've seen this. I've seen this.

[Host/Interviewer]

Like really good looking dudes have zero games, stumbling all over themselves, acting stupid and still end up with the girl at the end of the night. Cause they're hot.

[Yvette (Female Commentator)]

But then they may not keep her, you know, or you know, like it can only take them so far. But I do think, you know, good

[Jen (Female Commentator)]

looking people, people are insecure. I mean, first and foremost, make no mistake about it, because they, they're looking at themselves all the time, so to speak, like trying to find that perfect.

[Host/Interviewer]

Are you talking from experience here?

[Jen (Female Commentator)]

Yeah, yeah,

[Wingman/Coach]

but Brandon's a good looking guy.

[Jen (Female Commentator)]

Problems getting women. He'll attract a lot of women. I think once that confidence bar raises in terms of who he is, like Jen said, inside, what he has to offer, he'll be fine.

[Host/Interviewer]

And you got, I mean, you're not a bad looking dude.

[Brandon (Intern)]

Thank you. Quality of yourself.

[Wingman/Coach]

You're a cute guy.

[Host/Interviewer]

I don't think you're a hot piece of ass.

[Caller/Listener]

I think what it is is he

[Wingman/Coach]

doesn't have the experience.

[Brandon (Intern)]

You hear that, Alana?

[Wingman/Coach]

He doesn't have the experience of going up to a girl. So he doesn't know how it's gonna go, how it's supposed to go. So it's like the nervousness of approaching any new thing that any of us. I've never done fill in the blank before. You're nervous about it before. You've never, you know, before you've ever done it. Then once you get some practice at it, you're like, oh, I can do this.

[Jen (Female Commentator)]

Let's practice real quick. Brandon, practice on Jen real quick.

[Narrator/Advertiser]

What would you say?

[Wingman/Coach]

His boss. That's weird. Practice on Wendy before you practice.

[Yvette (Female Commentator)]

I do want to also commend you. I do think it takes a little confidence to come forward and be honest. Like, I think there's so many guys that would have never come on and said, you know what? I've been with one girl, you know, seriously, I haven't really dated outside of that. And I just want to, I want help. So many guys would have never said that. So I do think that you have that seat of confidence that we can build on.

[Brandon (Intern)]

Thank you.

[Host/Interviewer]

I wouldn't use it.

[Brandon (Intern)]

Hey, guess what?

[Narrator/Advertiser]

Guess what?

[Host/Interviewer]

You're the first girl I've ever approached in a bar.

[Jen (Female Commentator)]

Isn't this great?

[Yvette (Female Commentator)]

You will be the second girl I ever French kissed. It's gonna be so exciting. I'm just kidding.

[Host/Interviewer]

So what would you say? Okay, here's Wendy.

[Brandon (Intern)]

I've kissed at least three truth or dare in the Back of the bus counts in this situation. Spin the bottle yet? Seven minutes in heaven. At least I thought it was a girl. I don't know.

[Host/Interviewer]

So you're in a bar. There's Wendy. What's your. I mean, theoretically. What's your opening line?

[Brandon (Intern)]

I mean, I don't know. That's the problem. I don't know. Like, for me, like, I go, how you doing? That's. And I said. But mostly it's just the fact that you say, how you doing? I'm from New York. That's how I like. Then the attention turns to the fact that you say, how you doing? Weird.

[Female Commentator]

But that's good, though. I mean, that sparks conversation right away, even if you say it different.

[Host/Interviewer]

Icebreaker.

[Wingman/Coach]

Yeah.

[Female Commentator]

It doesn't matter how you say it. It just sparks some sort of interest in who you are. And she's gonna get to know you that way.

[Host/Interviewer]

What's he gotta do?

[Jen (Female Commentator)]

Dhalvette, first thing you say, just introduce yourself. Say, hi, I'm Brandon. Just say your name that way. It automatically. That's the first thing you say, you know? I mean, you're not. You're not, hi, how you doing? And then waiting for her to say something, she might say, I'm fine, and walk away. You say, brandon. Now, you identified yourself. You're hoping that she's gonna respond by saying her name. Now Brandon meets Wendy. And now Wendy and Brandon have a relation or a conversation about the spark. You know what I mean?

[Wingman/Coach]

It's so simple, but it's so true.

[Host/Interviewer]

And you don't have a name that you have to hide from. Like, I used to, like, make up another name because I didn't want to say, hi, I'm Burt. I used to have to say, like, hi, I'm Ian.

[Spanish Commercial Announcer]

Are you serious?

[Wingman/Coach]

That was a cool name.

[Host/Interviewer]

That was hilarious.

[Brandon (Intern)]

Because no one wants to hang out with a Bert.

[Yvette (Female Commentator)]

I want to ask Yvette a question about Brandon, too, because now Brandon, you know, I have been at events with him that I've hosted in social, events in which he's not trying to approach women. And he comes across as confident. Very entertaining. He gains attention without really having to do anything. Like, he naturally is a great.

[Jen (Female Commentator)]

Charismatic.

[Yvette (Female Commentator)]

Very charismatic and has a great personality. Do you think he overthinks when it comes to, oh, I gotta approach a girl now? Do you think he freezes himself out? What advice would you give him on taking that I'm not trying confidence into the I'm trying confidence?

[Jen (Female Commentator)]

You just said it. The key is, don't try. Don't try so hard when it comes to. I have to, you know, just be yourself. You have all the tools, obviously. You know what I mean? Just. Just be yourself.

[Brandon (Intern)]

Well, for me, at events, it's just like a switch goes on. Because my philosophy going in events, like, half these people I'll never see again. Most of these people I'll never see again, so what do I care what they think about me?

[Host/Interviewer]

Same thing in a bar.

[Female Commentator]

Same thing in a bar.

[Jen (Female Commentator)]

Just be yourself. I mean, don't, you know, confidence shouldn't be cocky. Confidence should be you just being relaxed. And, you know, you never lose because you have nothing to lose.

[Brandon (Intern)]

Yeah.

[Jen (Female Commentator)]

You know what I mean?

[Brandon (Intern)]

Yeah.

[Jen (Female Commentator)]

Just be yourself and you always win.

[Host/Interviewer]

Here's Ricky. Hey, Ricky. Good morning. You have some. Some advice for our intern, Brandon here?

[Ricky (Male Commentator)]

I do indeed. And Brandon, I think you've gotten great advice, but I've been listening to you. You have everything I was going to suggest. And Dolvett, I'm sorry to disagree with you. I think cocky and arrogance are two different things. Cocky to me, is a little bit of self. You make fun of yourself a little bit and you have a good time because you're confident. So I say cocky, sensitive, and funny. You get those three things in the first 15 minutes, she's yours.

[Host/Interviewer]

You got them all, dude. You got them all. You are funny.

[Brandon (Intern)]

Thank you.

[Jen (Female Commentator)]

You're good.

[Host/Interviewer]

You got them all. You're gonna be fine.

[Wingman/Coach]

You just gotta practice it.

[Brandon (Intern)]

That's the. How do you go and practice? Like, I can't look at myself in the mirror and work on a line.

[Jen (Female Commentator)]

Cause you gotta develop that muscle, so to speak.

[SpinQuest Promoter (Female)]

You can't help. Get out there.

[Wingman/Coach]

Trial and error.

[Host/Interviewer]

Like a trainer.

[Wingman/Coach]

Yes.

[Jen (Female Commentator)]

Who's a trainer in this room?

[Yvette (Female Commentator)]

Who said that?

[Host/Interviewer]

Here's the thing that will happen when you go out with Delve, and I'm serious about this, is that you're forced in a conversation with women. Because, honestly, I'm speaking for him, so he doesn't sound arrogant. So many women come up to him that if you don't engage with them when they come up, you look like an idiot. So. Which will be great for you because you'll be forced into conversation from his leftovers, which is fine. You want to practice on the leftovers, man, the runoff. That's where you want to be.

[Brandon (Intern)]

That sounds.

[Narrator/Advertiser]

Yeah.

[Yvette (Female Commentator)]

You're like the gutter to his roof.

[Safeway/Albertsons Announcer]

Yeah.

[Brandon (Intern)]

It's a vital part to the building.

[Wingman/Coach]

But I just put myself in the wives shoes, like your wife and all of your buddy's wives going Wait, what? Who are you talking to when I'm just.

[Host/Interviewer]

I'm just forced into talking to the leftovers, honey.

[Ricky (Male Commentator)]

That's it.

[Jen (Female Commentator)]

Wow.

[Brandon (Intern)]

Wow is right.

[Jen (Female Commentator)]

That's all I got.

[Wingman/Coach]

What do you say to that?

[Caller/Listener]

Wow.

[Host/Interviewer]

Hey, Edward, what's going on? You're on Q100.

[Caller/Listener]

Oh, what's going on, man? I'm just listening. First of all, I love you guys, man. You guys are triple. Thank you. But it is. It is rough out there. If you're not good. Look, if you're not so called good looking, especially in this society, man, you. You have to work twice or three times as hard, man, just. Just to get anything from the job to the female. And then. Why am I stuttering? This is my first time on the radio

[Jen (Female Commentator)]

at home.

[Caller/Listener]

Just to touch on. Oh, my goodness. I'm still stuttering.

[Yvette (Female Commentator)]

Just start singing. Nobody stutters what I'm saying.

[Caller/Listener]

Look, you just have to work too hard, man. It sucks. It honestly sucks. And it's just. You can't just approach a female these days neither. That's something y' all were talking about a while ago. I just believe it just isn't no more old school.

[Ricky (Male Commentator)]

It isn't.

[Caller/Listener]

Hey, how you doing? My name is Such and Such. You know, they either holding out their hand or they judging you off the rip.

[Ricky (Male Commentator)]

Say that.

[Host/Interviewer]

The one thing he is saying here, which I think is true, is when a guy like Dolvett approaches you and you're already physically attracted to the guy, it is way easier for Dolvett than if it's going to be for somebody that's not Dolvett. Someone like, if I was single, it's gonna be different.

[Jen (Female Commentator)]

I disagree. I disagree from the perspective of. Cause you don't know what Jen said.

[Host/Interviewer]

You don't know what it's like to be ugly.

[Jen (Female Commentator)]

Don't judge me if you have confidence. Honestly, no matter how you look or I don't think it's about looks' cause I've. I know guys that aren't the most handsome guys or women that aren't the most beautiful to look at aesthetically. But that confidence goes so far. You make me believe what you believe in based on what comes out of your spirit.

[Wingman/Coach]

Yeah, I agree with that. Absolutely.

[Female Commentator]

And all women are approachable. For him to say, you can't approach a woman, any guy who approaches you in general is confident guy, because that takes a lot of guts just to start a conversation. So, yeah, no matter what.

[Jen (Female Commentator)]

That's Brandon. I already gave him a nickname already.

[Yvette (Female Commentator)]

And if you go to a woman and say, hey, my name is Brandon. No woman's going to be offended by that. Especially in a bar. No woman's going to be offended. I'm being approached because that's one of the reasons she's there. Right?

[Jen (Female Commentator)]

You know, as opposed to hi, how are you doing? You don't want to do that. I don't introduce yourself. You're that confident that you want to give that attractive woman your name?

[Host/Interviewer]

Hey, Anna, good morning. You're on Q100.

[Caller/Listener]

Good morning. I love you guys. I just want to ask Dovette can he make an itune and I can just download his voice to my

[Host/Interviewer]

see how the rich get richer man.

[Yvette (Female Commentator)]

I want you to know too, what I love, I love doing because when he gets on the radio, then all of a sudden his voice gets, you know, and part of that game.

[Brandon (Intern)]

He also channel my dairy white.

[Jen (Female Commentator)]

This is my Denzel right here.

[Host/Interviewer]

So sometime over the next couple of weeks, our assignment is to take Brandon out and he's just. I mean, he's going to be your wingman for a night. Okay?

[Brandon (Intern)]

No jer bombs. That's just my no y practice makes perfect.

[Host/Interviewer]

Using a baseball analogy, now you are like going to the batting kit. You are playing in a game with Chipper Jones.

[Brandon (Intern)]

Okay? Yeah. He's like BP with the Braves.

[Wingman/Coach]

You need real confidence, not liquid confidence. Because these two, they're gonna pretend to drink and they're gonna have club sodas in their hand all night.

[Host/Interviewer]

Okay?

[Jen (Female Commentator)]

Don't tell them the tricks. Don't tell them the trick.

[Host/Interviewer]

The first show.

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