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Caleb Pressley

This Past Weekend w/ Theo Von

September 30, 2026

Caleb Pressley is an interviewer, content creator and host of the show “Sundae Conversation”. Caleb returns to talk about why he lives in a Florida retirement community, the ascension of Glenny Balls, and what went on behind the scenes at their Stagecoach DJ set.

Speakers Theo Von, Caleb Pressley

TopicsComedy

Theo Von (0:00)

He's a content catalyst, he's the interview assassin. You know him from his show, Sundae Conversation, with his cohort, Mr. Glenny Balls. I'm grateful for his return to the show. It's my friend, Caleb Pressley.

Bro, you kind of, I don't even need to say this in a negative way at all.

Caleb Pressley (0:35)

Don't say it.

Theo Von (0:37)

Okay.

Caleb Pressley (0:37)

What are you gonna say?

Theo Von (0:38)

But do you want to know it or not?

Caleb Pressley (0:40)

Well, obviously I want to know it now.

Theo Von (0:42)

Okay, I think they're used sometimes.

Resembles sometimes a trafficked woman. Nope.

Caleb Pressley (0:50)

Nope. Would have rather you not say it. Oh, I knew it.

Theo Von (0:54)

I knew it, dude. What we need to find is somebody who, when we want to say something, there's a mediator. There's almost like an escrow account.

Caleb Pressley (1:04)

You can put it in?

Theo Von (1:04)

Yeah.

Caleb Pressley (1:05)

Yes.

Theo Von (1:05)

It's like we say something like, I put a little, let me tell Terrence first and see what he...

Caleb Pressley (1:10)

Well, that way you can get out of your own body. Because I know you have a hard time sometimes holding stuff in.

Theo Von (1:14)

Well, yeah. I've had some mild nightly ejaculatory issues, okay?

I went on a run with the hand recently. Really? Yeah.

SPEAKER_3 (1:26)

What the?

Theo Von (1:29)

I'm a bot, homie. I have not been looking at pornography, so I am 52 days off of looking at porno.

Caleb Pressley (1:37)

Is that better or worse?

Theo Von (1:38)

Oh, it's good.

Caleb Pressley (1:40)

But to be on that large of a run.

Theo Von (1:42)

Oh, do you mean to still be doing pleasure myself or whatever?

Caleb Pressley (1:47)

Yeah, like what are you?

Theo Von (1:48)

Well, I'm jerking off.

Caleb Pressley (1:49)

Yeah, but like what are you thinking about?

Theo Von (1:52)

Oh, I'm thinking about women.

Caleb Pressley (1:54)

All the time, every time?

Theo Von (1:56)

Okay, I mean, look, I will say this. Every now and then you will see a guy kind of run by in the back of the fantasy, I will say that, but I don't know what he's doing and I don't know him.

Caleb Pressley (2:04)

You just get bored, it's like the big rock stars or whatever, they have a heart, after they just had sex with so many women, they're not even like gay, they just, eventually you get tired of women. And you jerked off so many times.

I mean, that's a good point, dude.

Theo Von (2:18)

Bro, jerking off is the gayest thing really because it's also ego, first of all, you're jerking a dude off, right?

Caleb Pressley (2:25)

Facts.

Theo Von (2:25)

Yeah, it's you. Facts.

But still.

Caleb Pressley (2:28)

You're a fat dude sometimes. Yeah.

Theo Von (2:33)

So I don't know, I got to look into it.

Caleb Pressley (2:35)

Dude, you're going to do something crazy about being a fat dude. This morning, I was in the shower.

Theo Von (2:39)

And are you feeling fat just to?

Caleb Pressley (2:41)

No.

Theo Von (2:41)

Okay.

Caleb Pressley (2:43)

I mean, if you did the math or whatever, if you did the scale or whatever. But I don't feel fat, I feel normal. It's probably a problem, I feel very not fat.

Theo Von (2:53)

Okay.

Caleb Pressley (2:53)

I still feel like normal, but every once in a while, I will catch a glimpse of myself, which this morning, I was in the shower, and my buddy FaceTimed me, and I had the phone playing music. And so I have a little stand on the back of my phone, so it kind of stands up. And you know how FaceTime, when it comes on, it shows you, it automatically pops up the screen of yourself.

Like if you pick up a FaceTime, you see yourself.

Theo Von (3:14)

Yeah.

Caleb Pressley (3:15)

And so I was in the shower, and I saw I was getting FaceTime. So I moved in the shower, and I noticed that the phone is still, it's not moving, but the screen followed me in the shower through like the shower window or whatever, had steam and all this type of shit on it, and it followed me all the way across, and I kept walking back and forth trying to get away from it, and it was just following me, the camera.

Theo Von (3:36)

So what do you see on like your screen's a gay dude or whatever?

Caleb Pressley (3:38)

Dude, the screens are just, they're on first of all, all the time. So you can just assume that if your phone's there, it's on you, and then it's, not only can you just like have it like this looking at you, you can point it like this, and it will still side eye you like this.

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