That Awkward Moment | Romantic First Dates | Love Love

Romance Rendezvous
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2 Video Views·Oct 29, 2025
# RomanticDates
Oh, look who's here. Glad you could make it.
Got to tell you, I'm really excited about this cover, guys.
Oh, hey.
Okay.
Hey. Holy ----.
Everyone, how's it going?
Good, good.
So, do you want to tell us a little bit about your approach with this cover?
Yeah, I'd love a little explanation.
It is what it is.
It is what it is? That's what you say when you get a parking ticket.
I know.
Looks to me like the guy here wants to escape.
Hmm. Does he?
And we want him to stay. That's the fantasy of men in this city.
It seems like she'll bring him home in the bag, totally trusting him.
And then after they sleep together, he'll prove to be too much of an asshole to actually stick around for a couple of hours.
So, tell me, Jason, why wouldn't the guy stay?
Hmm?
I thought you were a hooker.
What?
A hooker.
Why?
There were hooker signs.
What's a hooker sign?
You had on hooker boots.
Lots of people have them.
There were tons of condoms.
Did you ever think they might be there because I'm not having a ton of sex?
No. I thought they were a hooker sign.
What's a hooker sign?
What about the story of O?
It was research for a book.
There were envelopes full of cash.
I pay my landlord in cash so that he can commit tax fraud.
How long have you lived in New York?
An hour.
Wait, can I make it up to you?
Let me make it up to you.
You want to make it up to me.
Can I?
I don't know.
You can have my number.
And, uh, maybe you can.
Yeah, dude, everybody knows you can't call a girl a hooker.
Even hookers hate being called hookers.
I'm going to bring Ellie around.
No, you're not. No, you're not.
I'm going to get her on the roster.
Wait, a roster?
Yeah, a roster.
It's a group of girls that you're hooking up with that keeps you from sending the wrong message.
Which is what?
That you want to date one of them.
Right. You've got to start building a roster.
Yeah, it'll help ease the transition.
No, no, no, no, no. I do not need a roster.
Yes, you do.
Okay, I can't keep one girl.
What makes you think I can handle a bunch of them?
You just keep a bunch of them for a short period of time,
and then you send them out into the world to flourish.
Like college kids?
Yes, or like capitalism.
And then you replenish the team.
Think of a roster like a spiritual and physical...
Mostly physical.
...rejuvenation of the male soul.
Which you guys clearly don't ******* have.
Think of it like a spa.
A spa?
For your cock.
A cock spa?
Yep.
You just got to use whatever skills that you have available to you.
Girls love personalization.
Guys are idiots.
You're an idiot.
Darren.
Look, I'm sorry to barge in on you.
What are you doing here?
Okay, look.
I know that this is an awkward thing to do, but...
I have been having some pain.
And I just...
I don't know...
You came because you needed my help.
I came to apologize. I did.
You came because you needed my help.
Mikey...
I just...
I've been thinking about you.
It really was just a simple misunderstanding.
It was like, what kind of a girl would I be if I didn't eventually find it funny?
You'd be probably every other girl in the world, I think.
I'm really sorry.
But I'm not every other girl in the world.
No.
I guess you're not.
And then I kind of developed my own style, I guess.
And now you...
Design book covers, amongst other things.
Well, I guess you get people to believe in something.
Like, enough to want to buy it.
I get people to believe in the surface.
To do the one thing your parents told you not to do.
To judge a book by its cover.
Exactly.
Oh, we weren't supposed to do that.
You weren't supposed to do that.
See? I was encouraged.
Another example of just plain awful parenting.
But, like, the job that you have right now.
Like, is this something that you actually want to be doing?
You know what? It can be fun.
But do I love it?
You don't.
No.
Don't you want to love something?
Like, do you love what you do?
I started this new lecture series.
And authors can come along and they can talk about their work.
That's awesome.
Yeah, it's so great.
And people come?
No.
No?
No.
But I...
It's okay.
I mean, I figure that if I keep doing it, it could be a really, really amazing thing.
You should come along to one of them if you're around.
Oh, I don't know.
I can't really tell if it's important to you.
Sorry, it was a weird laugh.
This is my favorite place in the city.
Yeah, it's beautiful.
I know that I'm romanticizing the idea, but...
Come on.
That's kind of my dream.
You know, to have the key to Gramercy Park.
New York's charm is you're surrounded by things you can't have.
New York's charm is it makes you think you can have them.
You know, I'd love to look inside before we buy.
Me too.
In the meantime, we can go back to my place.
It's very similar, actually.
Except for everything about it.
I gotta get home.
Okay, yours it is.
You're one hell of a negotiator.
This kind of stuff just rolls off your tongue, doesn't it?
I'm just trying to make you laugh.
I don't like how well it's working.
