Season 1, Episode 14: The Old And The New

Episodes May 19, 2026

The waiter had brought Erica's salad but not my burger. I noticed that as I got back to the table after a trip to the restroom.

"So anyway," I said, catching her sneaking a bite, "I'm pretty bummed out about this. Keegan's inventory management system is perfect for Dixie's Chicken, and they would have been far and away our biggest client, and I just knew we had 'em. And then this morning I find out they're going with RDS. Heartbreaking."

Erica just smiled at me.

"What?" I said.

"You have so much passion for your business! It's kinda wild to see it. When we dated you were...different."

"What, you mean I was a drunk college kid?"

"Well, sort of. I mean, you didn't really have it together. But you were so young!"

"I was older than you."

"Not really. Like, what? Four years older?"

"Well, that was enough of a difference that I should have had my shit together. And all this time later I'm still busting my ass and just can't seem to hit that home run that changes the game."

"You will. I know you will."

"That's mighty nice of you. But... and I don't want this to come out wrong, because I'm really delighted that we're having lunch, Erica, what are we doing?"

"What do you mean?"

"I mean it was like three years and I never even saw you, and then all of a sudden there's Sasha's party and now a few days later and you're inviting me to lunch."

"Because you're one of my favorite people and I want to see you. What's so hard to understand about that?"

"Nothing, really. But it is sort of out of the blue."

"It's like I said. Jim's in Odessa this week and I'm sort of on my own, so why not have some Oscar time?"

"I'm not gonna complain. Even though it feels like... cheating, or something."

"Oh my God, I'm not cheating! Come on."

"Says the chick in the skin tight t-shirt and the leggings lookin' like the MILFiest MILF who ever MILFed."

She just rolled her eyes at me.

“I’ll have you know that I’m going to be a grandmother in like two weeks. Ann Marie’s eight months pregnant. And Stephanie just found out she’s pregnant, too. So this time next year I’m gonna have two grandkids.”

"So... a GILF?"

"You are so mean."

I laughed.

"Look," she said. "I want us to be really honest with each other, all right? Ever since Sasha's party I can't stop thinking about you, and the time we were dating, and..."

She trailed off.

"Spit it out," I said.

"And the robot. And I feel like I'm responsible, in a way."

"Responsible for what?"

"For the fact that you're alone! And... OK, I love my life, right? My kids are amazing, my husband loves me, we've always had money and we've done all these incredible things. Safaris in Africa, and Christmas in Lake Como, and... I know I'm rambling."

"Yes, but I'm certain that you're just about to get to the point."

She giggled.

"You're so funny! What I'm saying is that it's just in my head a little, like what if I'd made different decisions?"

"You didn't make a bad decision, Erica. You married a guy who's practically a robber baron and he's spoiled the shit out of you. What could possibly have been a mistake about that?"

"It'll sound horrible. Maybe I shouldn't say it."

"There goes the honesty part, I guess."

'Stop, OK?"

"I'm just giving you shit because I think I know what's coming."

"Fine. He's old now! All right? Can I say it? He needs back surgery. He's on like seven different medications and he hates taking all of them. And he's over there in Odessa, bunking with all the engineers in that house like he's 30 years younger because he's using work to prove he's not all washed up."

"I thought you said Michael was going to take over the company."

"Well, he is. But Jim can't let go. He's not aging gracefully. It's eating away at him that he can't do the things he wants to anymore."

"What, like sex or something?"

The look she gave me was a pretty clear yes.

"I'm sorry I asked," I said. "It's none of my business."

"It's fine. But yeah, OK? And I'm, like... this is really going to be a part of my life that's over?"

"Erica, you've had four kids by that guy. I think he earned the gold watch. Besides, you made the decision you wanted the old rich dude, and it worked out pretty damned well for you. I don't think you get to do the regret thing now that Jim's past his prime."

“Oh, come on. You know if things had been different, it would have been you.”

“That makes me feel absolutely wonderful. Thanks!”

“Would you stop? I'm just trying to say I like you and I always have.”

“OK, OK. I'll take that win,” I said, when what I really wanted to do was whine about the 30 years she could have spent as Mrs. Oscar.

"But you would have. Hit the home run, I mean."

"If you'd stuck around, you mean."

"It's just, y'know, what I've been thinking about."

"Erica, I was engaged twice after you left. It's not like it's your fault I never got married."

"But now there's this robot? And I didn't say anything at Sasha's party. You know how good I was. But I'm completely freaked out about the robot."

"I already explained this to you, E. There is no reason to lose your mind over Amber."

"I think you're in love with the robot, or something."

"Would you stop, please? Besides, the thing is I think you'd actually like her if you gave her a chance. She's cute as hell and she's really entertaining to have around."

"So you're in love with the robot and it's justified."

"Kim likes her. Kim is coming over tomorrow and she's taking Amber shopping."

"Because Kim likes you, dummy!"

"Ugh. Thank you, no."

"Why? What's wrong with Kim?"

"Oh, you've got to be kidding. Kim? Please."

"What? She's nice, she has a lot of money..."

"You have way more money than she does, Erica."

"But she has that trust, though."

"You mean that charitable trust that she and her mom run? Yeah, that's her 'job.' They get together once a month and write a few checks. Big freakin' deal."

"Well, now she's gonna be pals with the robot and you'll have her around all the time, and you'll eventually fall in love with her and you and Kim and the robot will live happily ever after."

"I think I maybe ought to smack you for sayin' that."

She laughed.

"What's too bad is that it isn't you instead of Kim," I said.

"What do you mean?"

"Being Amber's friend."

"Oh, seriously."

"I am serious. I actually think you'd have fun with her. Besides, she's a total clothes horse. You could do all your fashion magic on her and make her gorgeous."

Erica’s daughter Ann Marie was a total tomboy and didn't get past the flannel shirt stage until after she got married, and it drove Erica crazy that she never could teach Ann Marie any style when she was growing up.

"I know what you're doing," she said. "You're pretty good at it. But I know."

"I'm not doing anything. I'm just stating a fact. It sounds like you could use a project, and I can tell you that Amber would like absolutely nothing more on God's green earth than to be your mini-me."

"OK, enough," she said. "I'll... think about it."

I just smiled at her.

And then, finally, my burger showed up and we were able to eat our lunch.

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

But back at the house...

"Oh my God, I'm so glad that you're home!"

"Oh yeah? Why?"

"Because more stuff came! And I so totally want to show you what I've got!"

"Amber, you've got to be kidding. We can't keep buying clothes for you. We don't have the money, baby!"

"No, it's fine. I'll have you know that I'm a REALLY good shopper, OK? I'm getting these great deals on awesome stuff. You really ought to be proud of me!"

"Oh yeah?"

"Yes! So you go and sit down on the bed, and I'm gonna put on a fashion show for you..."

"Wait, before we do this - you got all the spreadsheets done like I asked you?"

"Ummm, yes! And I emailed them to you already!"

"All right then."

So I sat down on the bed, and...