Vault: Is she really out of his league?

Summary

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The Bert Show – Episode Summary

"Vault: Is She Really Out of His League?" (June 5, 2026)

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Overview

In this episode, The Bert Show tackles a classic dating dilemma: What should you do when you want to ask someone out who you feel is "out of your league"? Listener Jesse calls in for advice on whether—and how—to approach a woman from his class who he describes as "way hotter" than himself. The Bert Show cast (Bert, Kristin, Abby, Cassie, Tommy, and others) offer their trademark blend of humor and heartfelt advice, breaking down insecurities, practical tips, and the realities of first impressions in dating.

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Key Discussion Points & Insights

1. Jesse’s Dilemma and Self-Perception

• Jesse describes himself as "about a four" on the looks scale, while rating his crush a "15" (01:22).
  • "I'm about a four on the scale and she's about a 15." – Jesse (01:22)
• Admits to limited interaction: just about three minutes of conversation, mostly about commuting and class (02:10).
• The cast encourages Jesse to consider what he brings to the table besides looks—namely, personality and smarts (01:33).

2. The Role of Looks, Confidence, and Personality

• Bert and the cast agree that while physical attraction is a factor, confidence and personality weigh heavily once initial impressions pass.
  • "A lot of this whole dating thing is based on looks, especially first impressions, right?" – Bert (02:31)
  • "If you can overweight the looks with your confidence and your personality, I think that definitely outweighs..." – Advisor (02:39)
• Humor is repeatedly touted as a key trait that can outlast superficial good looks.

3. Practical Advice: Take it Slow and Build Rapport

• The team strongly suggests Jesse avoid immediately asking her out. Instead, they advise building a connection through casual conversation centered on class, shared experiences, or a possible study session (03:03).
  • "You've got to warm her up with other conversations...maybe a study thing where she can get to know you a little bit better." – Cast Member (03:25)
• Study sessions and innocent icebreakers are pitched as non-threatening ways for Jesse to become more familiar to her and display his personality (03:40).
• The importance of timing and not rushing things is emphasized (04:46).

4. Movie Scenarios and the “Friend Zone”

• Bert notes that sometimes, taking the “long route”—building a friendship—can lead to a romantic relationship, much like a movie trope (05:04).
  • "You pretend to be her friend for a long period of time and then she suddenly realizes...oh my God, he’s right in front of me." – Bert (05:04)
• They joke about the “friend zone” and how sometimes patience pays off, using themselves as examples.

5. Next Steps: Specific Icebreaker Strategies

• The cast brainstorms first conversation topics, recommending Jesse ask for help with class notes or clarification on a concept (06:04).
  • "Hey, I missed what he said last week about blah, blah, blah, like, could I borrow your notes...?" – Cast Member (06:04)
• The idea of using a study date as the first informal "date" is solidified by multiple show members (06:40).
  • "Hey, let's go get some coffee and study. And then boom, that's like date number one." – Caller (06:40)

6. Homework for Jesse: Make a Move (in Moderation)

• Bert gives Jesse a clear assignment: initiate a small, casual interaction about something in class—keep it simple, don’t push for a date yet (07:17).
  • "Your homework assignment...bring up something in class you’re just a little bit confused about. Maybe she can clear it up for you. It's just a little icebreaker today." – Bert (07:17)

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Notable Quotes & Memorable Moments

• Jesse: "I'm about a four on the scale and she's about a 15." (01:22)
• Advisor: "If you can overweight the looks with your confidence and your personality, I think that definitely outweighs..." (02:39)
• Bert: "What you're trying to do is the opposite here. You're trying to build for sort of long term..." (03:58)
• Bert: "It could happen. Dude, I held on for a long time with some women. Years. Be their friend, like nine years, some cases." (05:19)
• Caller: "Let's go get some coffee and study. And then boom, that's like date number one." (06:40)
• Bert: "Your homework...just a little icebreaker today. That's it." (07:17)
• Show Cast (playfully): “Boom, boom, bada boom, bada bing. You got an A on the test.” (07:03)

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Segment Timestamps

• Jesse Introduced & Explains Situation: 01:02 – 02:22
• Debate on Looks vs. Personality: 02:27 – 03:03
• Advice to Take It Slow, Build Rapport: 03:03 – 04:55
• Long-Game/Friendship Route Discussed: 05:04 – 05:28
• First Conversation/Study Date Ideas: 05:55 – 06:40
• Jesse Gets His “Homework”: 07:14 – 07:37
• Wrap-Up and Reflection: 07:42 – 08:00

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Conclusion

This episode authentically explores the anxiety and hope that come with asking out a crush, especially when self-doubt kicks in. The cast delivers a mix of playful banter and sincere advice: take it slow, be genuine, and use shared context (like class) to initiate interaction. Jesse leaves the call with a clear strategy—start with small talk about class, and let his personality shine through.

Listeners are left cheering for Jesse, with the cast promising to follow up on his progress in future episodes.

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Transcript

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[Car Buyer 1]

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[Car Buyer 2 / Bert]

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[Car Buyer 1]

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[Car Buyer 2 / Bert]

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[Car Buyer 1]

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[Car Buyer 2 / Bert]

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[Car Buyer 1]

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[Car Buyer 2 / Bert]

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[Car Buyer 1]

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[Car Buyer 2 / Bert]

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[Car Buyer 1]

I think your kid is walking up the slide.

[Car Buyer 2 / Bert]

Kyle.

[Advisor 1]

Again?

[Lady Luck]

Really?

[Car Buyer 2 / Bert]

Auto trader. Buy your car online? Really?

[Spinquest Announcer]

You're on the vert show.

[Host / Bert]

Here is Jesse, who's looking for a little advice here. Jesse, you want to be on the voice disguiser or no?

[Jesse]

No, that's cool, man.

[Advisor 2]

Okay, only if he's a Chargers fan.

[Host / Bert]

So you're about to ask a woman out that you consider totally out of your league.

[Jesse]

Oh, yeah. Oh, yeah.

[Host / Bert]

In what way? Like, she's just way, way, way hotter. She's a hotter woman than you are a guy?

[Jesse]

Well, let's put it like this. I'm about a four on the scale and she's about a 15.

[Host / Bert]

So now what makes you a four?

[Jesse]

You know, I'm just not one of those very attractive guys. You know, I've got a great personality, some decent amount of smarts, but I'm just not all that good looking.

[Car Buyer 2 / Bert]

How do you know this woman?

[Jesse]

School.

[Advisor 3]

School.

[Jesse]

She's in my class.

[Car Buyer 2 / Bert]

And have you guys worked on projects together or would you just be like a random classmate walking up to her?

[Jesse]

Random classmate? We just started. We just came back and she's in my econ class, so.

[Host / Bert]

So how much conversation have you had with her?

[Jesse]

Honestly, about three minutes worth.

[Car Buyer 2 / Bert]

What was it about?

[Jesse]

Basically, where we lived, we were talking about gas mileage and different things, and she's like, oh, I've got an hour drive. And it's like, oh, really? I do too.

[Advisor 1]

So do you guys live in the same area?

[Jesse]

Sort of. I'm in Cartersville, she's in Canton.

[Host / Bert]

Here's the thing. Let's talk real for just one second, okay?

[Jesse]

Okay. Go for it.

[Host / Bert]

Because I mean a lot of this whole dating thing is based on looks, especially first impressions. Right?

[Jesse]

Right.

[Advisor 1]

Kind of.

[Host / Bert]

So what do you mean?

[Advisor 1]

I mean, you can meet somebody and they may not be all that attractive, but I think what makes a person attractive is their confidence and the way they communicate. And the initial thing is looks. But I think if you can overweight the looks with your confidence and your personality, I think that definitely outweighs humor. Absolutely.

[Car Buyer 2 / Bert]

Women like funny guys.

[Host / Bert]

So let's go with this. So let's go with this for a second here. Okay?

[Jesse]

Okay.

[Host / Bert]

Based on what he's saying, she's way hotter than he is. So maybe if, probably most likely at first look, this is not a guy that she would be interested in looks wise. So would the best advice to be don't ask her out just yet. Sort of cozy up to her and let her get to know you a little bit more before you go for the asking out?

[Car Buyer 2 / Bert]

Yes, I would say that for sure. I mean, I think that you've got to warm her up with other conversations. Maybe start talking about the class or how, how she's doing in the class, whatever. And I think if you ask her out, it needs to be like based on what you've already talked about, which is the class. So like, I mean like, I think like a study thing where she can get to know you a little bit better, get to know your personality, you can be funny, laugh, ha ha, like study together at a coffee shop or whatever for like an hour. Like that's going to be a less threatening way to sort of like get to know her better and kind of work your way in.

[Host / Bert]

I think, you know, there's some guys, you know, that it's the other way around where they've got such great looks but such awful personalities. But they will get the initial date. They will get the initial date because they're so good looking and they may not get the second. Whereas what you're trying to do is the opposite here. You're trying to build for sort of long term here. She's not initially.

[Car Buyer 2 / Bert]

Then ask for the date.

[Host / Bert]

Right.

[Advisor 2]

Sometimes though, the great looking guy will get, you know, 10 dates out of it just because the women will keep. Well, you know what? He just hasn't opened up to me yet.

[Host / Bert]

Right.

[Advisor 2]

Look at his abs. Just hasn't opened up. You know what, that's why it stays like this, where I'm proud to be a man, where this superficial, shallow, nothing but a body attitude doesn't affect us at all.

[Host / Bert]

Is there any rush on why? You have to ask her out now?

[Jesse]

No, not really.

[Car Buyer 2 / Bert]

Do you know if she has a boyfriend or not?

[Jesse]

That is unknown.

[Car Buyer 2 / Bert]

Okay, that'd be a good thing to find out. Yeah, I think the more you talk to her and the more that you guys have like little, you know, chit chat conversations or whatever, I think you'll be able to learn a little bit more.

[Host / Bert]

Look, you may have to go the really long route here where you pretend to be her friend for a long period of time and then she suddenly realizes after one day, you know, after like hanging out for a year, that, oh my God, he's right in front of me.

[Jesse]

You know how it happens in the movie scenario?

[Host / Bert]

It could happen. Dude, I held on for a long time with some women. Years. Be their friend, like nine years, some cases.

[Car Buyer 2 / Bert]

I think the next thing we need to help him with is like, how does he spark up another conversation?

[Advisor 1]

Well, that's easy. They're in the same class.

[Car Buyer 2 / Bert]

So what do you think it should be about?

[Advisor 2]

Do you think? Do you think I'm good looking?

[Car Buyer 2 / Bert]

No. Do you think I'm gonna go with no on Jeff's idea?

[Host / Bert]

There's gotta be something there, man. I mean, you're in the same vicinity as she is every single day.

[Car Buyer 2 / Bert]

Right?

[Host / Bert]

There's gotta be a moving forward line or something.

[Advisor 3]

Okay. Okay.

[Host / Bert]

Do women dig it when guys come to him with something that they, they aren't sure of? Like something in class that he needs an answer on just to break the ice?

[Car Buyer 2 / Bert]

I think she'd be happy to probably be the expert. Like, hey, I missed, you know, what he said last week about blah, blah, blah, like, you know, could I borrow your notes or something like that?

[Jesse]

Okay.

[Host / Bert]

Can you do that?

[Jesse]

I can do that.

[Host / Bert]

Do you get all nervous and stuff around to where you can't talk and.

[Jesse]

No.

[Host / Bert]

Okay.

[Car Buyer 2 / Bert]

Throat gets dry and you're like swallowing

[Advisor 2]

really loudly sometimes to yourself a little bit. If she does say that, you can use her notes. You should ask her to put her notes up her shirt and ask her then if you can go get them.

[Jesse]

I can do that. No, no, don't do that.

[Host / Bert]

Hey, Jason, good Morning. You're on Q1.

[Advisor 1]

Hey.

[Advisor 3]

I definitely think the dude needs to get a study date going because, I mean, it's real easy. You know, you need to study. So it's like, hey, let's go get some coffee and study. And then boom, that's like date number one.

[Car Buyer 2 / Bert]

Boom. Then you're in there.

[Advisor 2]

Boom, you're in.

[Car Buyer 2 / Bert]

Boom.

[Advisor 2]

Once you say the boom. There you go.

[Advisor 3]

That's right.

[Advisor 2]

Invite her over for lasagna.

[Car Buyer 2 / Bert]

Boom, boom, bada boom, bada bing. You got a A on the test.

[Advisor 3]

She got a A.

[Car Buyer 2 / Bert]

Then you're in there.

[Advisor 1]

Hey, I feel like I'm on an episode of Jersey.

[Host / Bert]

Jesse, are you gonna see this girl today?

[Jesse]

Oh, yeah.

[Car Buyer 2 / Bert]

Awesome.

[Host / Bert]

Okay, so your homework assignment for today from the bird show is bring up something in class that you're just a little bit confused about. Maybe she can clear it up for you. It's just a little icebreaker today. That's it. You're just trying to get a little interaction, and then we'll work on something a little bit more advanced, like next week.

[Jesse]

Sounds good to me.

[Host / Bert]

Okay, dude.

[Advisor 3]

All righty, man.

[Host / Bert]

Godspeed, Jesse.

[Jesse]

Hey, thanks, Bert.

[Host / Bert]

All right, we'll talk to you tomorrow morning.

[Jesse]

All right, bye.

[Car Buyer 2 / Bert]

Bye.

[Host / Bert]

Man, that walk up to her when you know she's so out of your league is so nerve wracking.

[Car Buyer 2 / Bert]

Aww.

[Host / Bert]

It's the worst.

[Advisor 1]

He's got the N. He's got the N. They're in the same class. He's got an in. He's fine.

[Host / Bert]

All he's got to do is say, look, there's something I'm a little confused about. Just a little icebreaker today.

[Car Buyer 2 / Bert]

I think this is gonna be fun to follow. It will be, especially if it works.

[Bluff]

Listen, it's the vert show.

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