Season 1, Episode 9: Starved For Attention

Episodes May 18, 2026

I've got a group of guys who meet for drinks at happy hour once a week, and we alternate picking up the tab. And the victim having to pay for everybody picks the place.

My usual choice is a Cuban bar not too far from the house called Bolero. It's a very cool upscale dive that a friend and former client of mine put together essentially as a knockoff of a famous Cuban bar in New York that didn't survive Bill DeBlasio. Terry went up there and saw the place, fell in love and swore he'd make a bar just like it. Then he started his place down here in 2019. I helped him get it off the ground, and then COVID hit and he managed to hang on for dear life.

I lost him as a client, because he just couldn't afford me. But we stayed friends and I'm a loyal customer anyway. And while his place is awesome, he's still not killing it business-wise. Bolero does a decent little private-party business and once in a while he'll have a good crowd, but it's not really consistent enough that you'd say it's a happening place.

I could help him make it that way, but I'm not going to do it for free. And my experience working with bars and restaurants has given me the firm conviction that I absolutely do not want to be an investor in one, which Terry has floated the possibility of.

So anyway, I left Amber alone with the first of what I'm sure would be an interminable number of Amazon packages, and I left for Bolero where I was due to host Mike, Theo and Drew for our happy-hour get together. Getting there a little early gave me a chance to flirt with Diana, who was the best thing about Bolero.

Before, I mentioned that I'd be perfectly happy with a friendly, honest and reasonably hot 20-something bartender rather than a society chick. That wasn't a hypothetical. Diana was the one I had in mind when I said that. I'd wife her up in a New York minute, except she was probably out of my league.

Diana wasn't a gold-digger, but it's like the song goes. She ain't hanging with no...well, you know the rest of the verse. I needed a bigger uptick in my business' growth before I'd be able to escape the friend zone with her.

But it's not like we didn't get along.

"Hey, Oscar. What's going on?"

"Howdy, ma'am. I have my three assclown friends coming, so we're gonna get a table. Can I get started with one of your ridiculously awesome mojitos?"

"You may. Coming right up!"

"How are things with whatshisname?"

"With Jasper? Oh, that didn't last."

"I thought you were getting serious with him."

"Jasper isn't a serious guy. No thank you."

"I agree. You need somebody older, who has his act together and can handle himself..."

"And has a big house and a boat."

"Right."

She just laughed and delivered my drink. And then one by one in quick succession the others in my group showed up.

I decided not to tell them about Amber. That was a conversation I'd rather have with them individually.

--------------------------

Finally, after a couple of hours with the guys and then a few minutes longer of half-assed flirting with Diana as I paid the bill, I said goodbye and headed home, only to find someone a little miffed at me at the top of the stairs.

"Oh, look who finally showed up!"

"I said I'd be gone all day. You're not mad at me, are you? And how about that. Totally different hairdo!"

"Well, I got lonely here by myself. "

"You had the dog to play with all day."

"That's true, plus it was workout day. I actually had a lot of fun!"

"Amber, you're such a ham. How long have you sat up there planning to make me feel guilty?"

"Oh, I don't know. Maybe an hour. Oh, wait, I have laundry to do!"

"You're doing it now?"

"Just this load...and the next one."

"So we didn't get a ton of housework done."

"Well, I was going to do the dishes, but I had questions about the pots. So how do I..."

"Yeah, baby? Not tonight. I'm exhausted."

"Wait - you have to let me show you the workout stuff I'm doing. I found all kinds of stuff online. You'll love it!"

"Workout stuff for what? Dolls?"

"Totally. It's like Doll Pilates. First, you..."

"Doll Pilates? Please, please tell me you didn't sign up for a membership or anything that I have to pay for."

"Ummm, no."

"Amber?"

"I swear. So look - first, there's the tennis balls. I have to squeeze on them for 10 minutes straight."

"I'm not going to watch you squeeze tennis balls for 10 minutes."