Season 2, Episode 10: A Winning Streak

Episodes May 22, 2026

It was the Thursday the week before Thanksgiving, and I was having a big day.

That morning, I'd closed a consulting deal that I'd been trying to get since before COVID - Senoritas Mexican Grill, which was a decent-sized regional chain of Mexican restaurants based out of New Orleans. A buddy of mine had moved up to VP of Operations there, and so I finally had a warm contact to get their business.

And I'd done it.

It so happened that day I was due to eat lunch with Ted Loria, an old friend of mine. I didn't get to see Ted as much as I wanted. He was the very personification of a family man - that and he had a job as a lawyer for one of those slave-driving big law firms doing boring contract law. So palling around with bachelors like me wasn't something Ted had a lot of time for.

Ted wasn't having as big a day as I was.

"It didn't happen," he said. "I mean, I always knew it wouldn't, but... passed over for partner again, and I think that's it for me."

"Let me get this straight," I said. "You had your annual review, and they came back with an A-rating on your work product, said you're great, and yet you don't make partner and they're not offering you a raise? Why not?"

"Because I don't bill enough hours, man."

"You work 50 hour weeks for those guys."

"I work 45-hour weeks. They know my kids come first. And they say it's awesome I'm a committed dad and husband, right before they crap on me because of it."

"That's such horseshit," I said. "Reminds me why I refuse to have a boss."

"Yeah, and you refuse to have a wife and kids, too. Oh, by the way, how's the robot?"

"Haha! I almost brought her with me so you could meet her. But she's working."

"Working, like what? Being your maid?"

"Somebody else's maid, actually. She has this job for this company that sends girls in French maid outfits to clean your house for an outright stupid amount of money."

"Dude, Les Servantes? They were talking about that at the office. Old man Saunders has them come and do his place once a week."

"Great. Yeah, that's where Amber works."

"Pimp out that robot, bro! I like it."

I gave him a shitty look and he laughed.

"So you're the consultant at Senoritas now, huh? Can you get them to do something about their margaritas? Nowhere near enough tequila in those."

"I'll put it up the line, Ted."

"But really - congratulations, man. I'm proud of you. I know it's been brutal trying to claw your way back from what COVID did to you, and now you're winning."

"Thanks, buddy. That's really sweet of you!"

"Fuck you," he said with a laugh. "Seriously, though, what you ought to do now that you've got your business going again is get out of that little place you live in."

"I like that little place, Ted. And you absolutely cannot beat that location and that neighborhood. I'm so freaking spoiled over there."

"You have, effectively, one bedroom. And your Robot #2 has taken over your couch. How do you even watch football?"

"How do you? Ashley and those three rugrats of yours don't let you watch the game even in that mansion y'all live in."

He laughed.

"Call my wife and hire her. She's the best realtor in town. Have her find you a house that says you aren't a brokedick."

"I know she is. I need to."

I loved Ted. To me, Ted is a hero. But he's also a walking cautionary tale.

He and I go back to his wedding to Ashley. I knew her before him, and she was the one who introduced us. I was a groomsman in their wedding.

And I knew Ashley through her sister Felicity.

Let me give you a little bit of a back story at this point. After Erica, while I was finishing up my MBA, I dated Felicity for about a year. She was more cute than pretty, but she had this huge, fun personality. There was never a dull moment with her. Felicity was the girl who did everything she could to make you laugh. It was a lot of fun dating her.

And for where I was in my life, which was that I was still in school and tending bar four nights a week, going out with friends practically every night, she was a great fit. Felicity would come and hang out at the bar where I was working and she'd play greeter with everybody else there. It was great.

I really liked her family and they liked me, too. It turned out that Felicity's little sister Ashley, who was 13 when I met her, eight years younger than Felicity was, liked me best of all.

Ashley had a huge crush. Everybody laughed about it.

Everybody but Felicity, that is. And it was strange, because that was the one thing Felicity took seriously. Everything else was a joke but it got to the point where she and her sister were barely talking because Ashley couldn't handle boundaries.

Again, she was 13.

I figured Felicity was going to be The One. I wasn't head over heels in love with her, but she was good for me and we fit. She had a job working retail, and that was really the extent of her professional ambitions. She was waiting for somebody to wife her up.

And yet, when I raised the idea of us tying the knot, she resisted it. She just wanted to have fun, she said. Why mess with things the way they were?

I even did the old-fashioned thing of going to her dad and asking for his blessing. He gave it, but he said it was going to be years before Felicity was mature enough to be wife material. I was 24 at that point and she was 20.

And this mattered, because I was about to graduate from the MBA program at LSU, and I essentially had a choice of either taking a job as a 9 to 5 corporate stooge with the local office of my dad's company, a job that had a solid future to it but not an amazing starting salary, or go and be an account rep for that food service company and hang out with the fun service industry people at all hours of the night.

My dad did the 9 to 5 thing all his life. He carried it off fine. He saved his passion for a couple of things - hunting and his family. And he mastered the art of directing just enough energy to his work to be good at it. So he moved up, made decent money, and he and Mom and my older brother and me did great as a family.

If Felicity wanted to get married, I'd just go down my dad's path. It was comfortable, I knew what it looked like, I had my dad's example and there was an easy plan there - have a couple of kids young, ride out their childhoods as you're climbing the corporate ladder, get them through school and then coast to the finish line with a nice nest egg in tow. Felicity was a perfect wife for a ride like that; she would make it fun.

But if she wasn't going to be on board with the plan, the food service rep job was a better fit for me. I already knew that business; the bar where I worked kept trying to make me the manager, but I didn't have time to do that job while I was in school and they couldn't afford me once I graduated - and I was going to make at least as much money working pretty much on my own schedule.

And I even presented those options at the table one night Felicity's folks had us over for dinner.

She basically froze when I put the choice out there. Her folks were behind Option One. I said I could go either way, but my default was Option 2 because I knew I'd make more money right out of the gate. That pretty much left it in her hands.

Not only couldn't she make a decision, she threw a fit about it. She dragged me into the back yard and read me the riot act about why my life was somehow her responsibility, and how manipulative I was for putting all this on her.

"I'm trying to make a big life decision which could affect you," I said. "Are you really going to be mad at me for including you in it and asking for your input?"

That only made it worse, and Felicity's mom came out to break up the fight.

And it wasn't very fun with Felicity after that.

She ended up moving to Memphis after college, dated a musician who got her into booze at a level I couldn't even touch, and she ended up in rehab and AA. Where she met a corporate stooge who worked for FedEx and they were living happily ever after with a fridge full of non-alcoholic beer.

Meanwhile, Ashley kept up with me. All through high school, all through college and when she moved back home after she graduated. By that point she was dating Ted, and she insisted he and I become friends, which was easy to do, and I was in their wedding. I'd been a friend of the family ever since.

Ashley was the one married-woman friend I had who never tried to set me up with any of her girlfriends. It wasn't a well-kept secret why.

And Ted was one of my fishing buddies, though he was a terrible fisherman. I'd take him out on fishing trips in the Gulf every couple of months, and it was always fun.

Ted was a sufferer. He would take bullets for his family, and pretty much did. When he was a young attorney and they were just squeezing out those kids, he would take time off work to be with them. One time he ran afoul of old man Saunders, the managing partner of that firm, and was denied a promotion he was up for because he left the office to attend a piano recital. It didn't matter that he went back after dinner that night to finish a brief he was working on; Saunders called him in and bitched him out for the "bad optics" of his abandoning his post.

And he limited his hours at that firm so Ashley had some time during the day where she could pursue her career as a realtor. He sacrificed his career for hers and she ended up making more than he did. In a lot of marriages that's a problem. Maybe it was one for Ted and Ashley, but if it was they sure didn't advertise it.

And Ted goes to everything. Little League baseball, ballet practice, piano recitals, travel ball. His life is totally subsumed under that of his wife and kids.

I was in awe of that. And it utterly terrified me. Ted was my Dad on steroids. And the fact that I was completely terrorized at the prospect of living like he did made me think I lacked character. Was I too self-centered to be a man like that?

Or was Ted just a virtue-signaling pussy?

But of course, Ted had Ashley and I didn't, which mattered.

Felicity was more cute than pretty. Ashley, even after pumping out three kids, was a knockout. More than that, she was everything Felicity wasn't. She was funny and engaging but she was also whip-smart, wise, and an absolute rock when it came to being a wife. Ted never shut up about how much validation he got from her, and how without it he couldn't do what he did.

Yeah. They were pretty much my favorite people on earth, even though they intimidated the shit out of me on a couple of levels. Hire Ashley as my realtor? Of course I would.

‐‐----------------------

I was in the office and I could hear that Amber and Katie had made it home. It sounded like they weren't fighting, too, which I regarded as a nice blessing. I was e-mailing back and forth with Michael Stafford, trying to settle on a price for the forensic audit of Stafford Oil and praying he wouldn't ask me about my latest encounter with his mom.

But I wasn't so busy that I didn't have a smile for Amber when she poked her head in.

"Awww, look at you," I said. "You're so cute in your I've-totally-given-up-trying-to-look-hot-anymore outfit."

"Go ahead and make fun of me... again. I'll have you know it's cold out there and I can't really get warmed up, and I'm not allowed to be cold when I'm working, so, y'know... deal."

"Deal? That's all I get?"

"Well, that and my eternal, bottomless love, yeah."

"Awww. Well, I'll have you know that we got the Senoritas account, so a celebration is in order."

"Oh, wow. Really? That's pretty cool. But... what kind of celebration?"

"What kind do you want? And no, getting in bed and cuddling is not going to cut it."

"Rats! Because that's what I would want to say."

"Nah, nah. You have to be Fun Amber for me. I want to go out."

She gave a forced smile. "Okay," she said. "I mean, if that's what you want..."

"I'm having trouble believing these words are leaving my lips, but I'll take you shopping. How about that?"

"Boy, you really are in a good mood. Either that or you've lost your mind."

"What I'd say is I want to celebrate in the worst way, and that's pretty much the worst way I can think of."

"You're funny. OK, but, like, I'm so cold. Can I go and sit in the bathroom for like 15 minutes with the heater on?"

"Yes. If that will make you cease your whining, you can use your little makeshift sauna in there. But after that, you, my dear, are getting dressed and we're going to do something fun."

Her smile wasn't forced this time, and she pranced off to the bathroom where she was going to cook herself warm.

So I went back to my emails, and well more than 15 minutes later...

"Oh my God! Would you close the door?"

"No, baby, sorry. It's time to go. We'll go buy some things we don't need and then you have to go have a drink with me somewhere."

"OK, but..."

"But what?"

"I'm dressing warm."

"Fine! Would you just haul ass, please?"

She stuck her tongue out at me as she passed, and then gave me a peck on the cheek.

And a couple of minutes later, she'd managed to look like a million bucks even with bundling up like it was the Yukon outside.

"See? That wasn't so hard," I said.

"I look good, huh?"

"Yeah. You'll do."

"Are you rich enough yet to buy me a real fur coat? I've kinda decided I want one."

"I'm not really surprised, but I think it might be next winter before we can pull that off," I said.

"OK, honey. I love you anyway."

So we went, and she took it easy on me - actually insisting that we buy some stuff for me rather than her. And then we did dinner and drinks.

I told her that I was probably going to get together with Ashley and start looking for houses.

"Well, that cinches it, then. I'm gonna keep on working."

"I was actually thinking the opposite. You've got like six weeks left in that lease, so my thought was that I'd just cut Stella a check and buy you out of it."

"That's dumb. What would you do that for?"

"Because I don't like the idea of you spending so much time with Dan Cole at his house. And honestly, the Paula thing is off-putting."

"Don't waste your money. I'm good doing this until January, at least. Honestly, honey. So what kind of house are we getting?"

"We need at least three bedrooms. Actually, we need four, because one of them would be an Amber and Katie room, or at least a Katie room, and we should have an actual guest bedroom, and I still need an office."

"And a yard for Rufus so we don't have to walk him."

"But he likes people taking him for walks."

She shrugged. And then she kissed me.

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

Then it was Thanksgiving, and I flew up to Dallas to see Mom and Dad, not to mention Tyler, my older brother, who... we'll leave the Tyler story for another time. I left Amber and Katie in charge of the house and of Rufus, half-expecting to get panicked phone calls reporting some horrific disaster.

But nope. It was all quiet on that front.

And when I got back, Amber told me that I was probably going to be a little disappointed in how much Factory Girl time I was getting.

"We're booked absolutely solid until the week of Christmas, baby," she said. "All these people are getting their houses cleaned for the holidays and the word has gotten out about us."

"Damn," I said. "So what? I'm just on my own until Christmas Eve?"

"I know. I'm sorry. But I can't really bail on Stella. Oh, but wait! So on Saturday while you were gone, she had Katie and I over and she sat us down and asked us about re-upping after the three months were finished. Katie's like, 'Oh, if you're paying me I'm totally in.' And then Stella asked me what I want to do, and I didn't know what to say, so..."

"Well, how did you leave it?"

"I did plant the seed about being her office manager."

"How'd that go?"

"Well, she was kinda insulted, I think. But I said having somebody who does the little things for her, especially with business being as crazy as it is, is just a smart call. I think she's at least thinking about it."

"Well, let her think about it, because if she wants you working for her after January, that's what she's going to get."

"Ooooh. Tough guy Oscar!"

"No. My business is starting to take off, and I want my personal assistant back. And I like you better than Katie."

"She's better at doing paperwork than I am, though."

"But she's not as much fun."

"Well, that's for-sure true!"

"See? That's what I'm talking about."

And then I left to meet Ashley, who had her first house to show me.

"OK, I'm showing you this place not really because I think you should buy it. But I want to see what you think of it so I'll know what we're looking at. It's in the price range you said. So?"

"I don't know. I kinda had it in my head that I'd get an old house. There's a lot of character in a place with some history, you know?"

"Yeah. I know. Those can be real fixer-uppers, though."

"I'm OK with that. In fact, I have this thing in my head that maybe what I'd do is spend the next few years flipping houses - buy one, live in it for a couple of years while fixing it up, then sell it."

"Ted and I have had that same idea! Well, not living in it, but... you know that he worked construction to put himself through school, and he's mentioned that maybe that could be a weekend thing he could do. Fixing places up that we'd sell."

"It'd be a cool project. If I had any money to invest with y'all, I would."

"Oh my God, that would be so much fun!"

"Yep."

All of a sudden there was a strange pause.

"You seem... different."

"I do?"

"Yeah. You're carrying yourself a little... I can't describe it, but you seem more confident, maybe?"

"Well, business is finally going better, so I'm feeling good about that. And, I dunno."

"Ted says you're seeing Erica. That's the one that got away, huh?"

"I don't know if there's anything really going on there. But it's been nice reconnecting with her."

"Hmm."

"What?"

"You look like a married guy. Or a guy in a good long-term relationship. I can tell the difference between guys who are attached and guys who are single. It's almost like an aura. You've got a positive thing about you. Like somebody loves you. It looks good on you. I'm just trying to figure out what that is."

I laughed.

"If I told you it would piss you off," I said.

"Ohhhh. The robot does this for you? It's, what's her name? Amber?"

"I guess. She's the only constant in the mix. That, and I'm not doing the frenemies-with-benefits thing with Peyton anymore."

"Oh, thank God for that. That woman has been such a toxic influence in your life."

I laughed. Ashley straight-up hated Peyton.

The next thing I knew, Ashley was in my personal space.

"Maybe I shouldn't be doing this," she said. "But I feel like I want to show you every house in town. It's kinda like the only way I can get you to myself."

"And why do you want me to yourself?" I asked.

"You know why. You've always known. And now? With this thing you've got going? I don't know, Oscar."

"You're right. Maybe we shouldn't be doing this."