Holmes Returns Again
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How did Caleb and Holmes turn a hotel night into an unforgettable Pride dance floor story?
Wave.
A lot of people were like, oh, I do feel non-binary. And this has been a thing for like thousands of years, like a third gender. And I'm noticing this because I'm not being under the gaze of a really patriarchal, dominant society for a second. I'm understanding this. And then a lot of them did feel like I have to take this back because not only is it being teased a lot, it's being like truly like put in danger by our government.
Yeah. I think there's just boys and girls.
Yeah.
Are we rolling? Oh, oh, oh.
She's like... Of course we're rolling, Holmes.
That's you going to the club the other day. What? When you got us in somewhere really, really long and I'd never seen it. You hate this.
You were... Yeah, yeah, yeah.
You were really weird about this. I had never seen it. You were like...
People have no idea what you're talking about. Do you want to explain?
Yes. Well, so I get in from filming Overcompensating Season 2. Kayla was so fucking sweet. Not usual for him looking at the camera. Just kidding. Oh, there it is. He's waiting at my hotel with like a bunch of sweets and weed. It really meant the world to me. And then I was like, I just want to stay in the hotel forever. I just want to lay down. And then at 11 p.m., I had a second wind.
The whole day you were like, I'm not leaving the hotel. We're not doing anything tonight. Don't plan on it. I was like, okay, we won't do anything tonight.
I knew it. He did this new technique. Because normally... You did.
You did a new technique. I'm finding new trickery in ways around Holmes' boundaries.
It actually worked really, really well. It did. It was crazy because I really felt like I had gotten past you kind of tricking me in new little sneak ways. And I was like, new technique. And he kept being like, I don't know what you are calling this new technique.
They were like, I'm setting a hard boundary. My energy is such that I just, I can't go out tonight. I'm not leaving the hotel. I was like, sounds good. We'll sit in the hotel. Yeah, yeah, yeah.
He was like, we'll be in the hotel. He was like, I don't even want to go dancing, really. Not worries. But then you would have a teeny, a teeny, teeny one. Yes. And so then all of a sudden... 11 p.m.
strikes and what happens?
Well, and you did something really, really sneaky too, which is what kind of weed did you bring me? A perfect sativa. A perfect sativa. So I have a little sativa. I brought you goofy weed. I'm like, I have to take a shower. And then all of a sudden I come out. Aiden and Caleb are there. I go, let's go dancing. And we had a second wind. Huge. But it was the last weekend of Pride. And so it's funny because I like telling them the story. It's the last weekend of Pride. And so we try to go dancing. And first we go to a beauty bar. And it's like there's a huge line outside the dance floor. It's like so crowded. There's no way.
There's a line to get on the dance floor that's like...
metered by a security guard i was like what what happened to new york city wait but then do you remember what happened we were like we there's a screen and we're like oh that must be where people are dancing but everyone was standing really really still and we're like i guess not and then all of a sudden it was yeah why there was a cctv screen we were like that must be on the dance floor but no one's moving i wonder if it's frozen and then immediately people started doing the ymca but they were like so jam-packed so it was like anyway so then i was like fuck we might not be able to go dancing which i won't replace and we tried We go there and it's like, the line is so long and I'm thinking like, you know.
We'll bleep the name of the place.
We'll bleep the name of the second place.
Oh, bleep it, totally. Bleep it. And then, yeah, bleep a couple things throughout. And then, I'm so happy to be here. Okay. And then basically, oh, I was like, we won't be able to go. Let's just go eat or whatever. And then Caleb like makes eye contact from afar with like one of the bouncers and is like. puts up the number three and then all of a sudden we're walking in and I was like, I'm like soaking wet.
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Chapters
7 chapters
1
How did Caleb and Holmes turn a hotel night into an unforgettable Pride dance floor story?
0:01–5:59
2
What fan interactions and boundary moments do they describe from late-night outings?
5:59–34:12
3
How did a week of silence, flowers, and a tense voice memo reveal friendship dynamics?
34:12–47:02
4
How do Holmes and Caleb debate AI’s real-world harms and uses?
47:02–50:45
5
What do they reveal about gender identity and being non-binary?
50:45–53:54
6
Why are the hosts concerned about anti-trans laws and how can allies help?
53:54–1:01:55
7
What is the ‘gooby girl’ idea and why are they launching a festival to protect it?
1:01:55–1:26:38