A customer asked: Why would a woman date a loser?

Tony had been a regular for a couple of years. I enjoyed everything about him and lit up when he came to visit at the Penthouse Club. He reminded me of a kid from high school—the short guy on the basketball team who still managed to carry his weight with fast moves, scoring lots of points. The two even had the same look: Italian, with thick, dark hair and a bright smile. As a cheerleader, I paid special attention to him on the court. He was my secret little crush.

Tony used to call me Renaissance Woman, which made me giggle and feel seen. I was interested in everything and Tony appreciated that about me. 

We’d get into philosophical conversations all the time. So it didn’t strike me as odd when he posed a hypothetical: Why would a woman date a loser?

I gave this some thought and said, “Well, I guess when a woman sees a bird with a broken wing, she wants to take it home and nurture it back to health.”

Tony let that sink in for a moment. Then he scoffed, “When I see a bird with a broken wing, I think: that’s an easy lunch.”

I hid my reaction well. Had I expressed what I was feeling—shock, disgust, disappointment—our night would’ve ended right there. But I had money to make. I responded with, “Oh gawd,” and moved the conversation along.

I liked Tony. It hurt to hear him say something so cruel. 

He never treated me cruelly. Tony was respectful and reliable. He was a dream customer, really. If he said he was coming in on a particular night, he was coming in. He never canceled, never made excuses. And he had plenty of legitimate excuses. The man was busy. And often tired. 

One time he showed up at Penthouse just to tell me he was tired and was going back to his hotel to take a nap, but he’d be back in a couple of hours. I thought there was no way he’d be back. Once he went to sleep, he’d stay asleep. But Tony kept his word. 

He was back in about two hours. We went to a pricey private room, and he gave me a generous tip. It meant a lot to me that Tony never canceled. He understood that I was working. I looked forward to his visits for the money just as much as his company.

Tony was from somewhere outside Chicago. I imagined a pristine suburb, like Rye or Greenwich. He worked in private equity and traveled a lot for work, mostly around the U.S., often between Chicago and New York. 

His schedule was brutal. He’d fly somewhere, have meetings all day, then fly home and go straight from the airport to coach his son’s baseball practice. Tony was super type-A: an excellent provider, an involved father, and ripped-abs fit. 

He didn’t understand why his wife “couldn’t handle her job.” He frequently complained that she didn’t run a tight ship at home. The kids “walked all over her.” She didn’t “enforce discipline.” She was always depressed and overwhelmed. Tony came home “in the mood for sex.” She usually wasn’t ready yet. 

Tony felt that it was his job to make the money, her job to run the house, and he couldn’t understand why she struggled with her end of the deal.

Tony wasn’t the only type-A customer who felt this way about his wife. I’d heard this before. 

One night in a private room, Tony shared something with me: his wife was having an affair with the gardener. 

I thought back to that seemingly random question he’d asked a few months earlier. Was the gardener the “loser” Tony couldn’t fathom a woman finding attractive?

I knew a gardener once. I wrote about Louie earlier, in an entirely different context. 

My mother dated him when I was in elementary school. Landscaping was his family’s business. His father was getting old, and Louie was taking over. 

Louie was kind to me. He drove a red pickup truck and let me ride in the back, wind in my hair.

(My entire Gen X childhood would be illegal now.)

The three of us would ride in that truck to his land in Berlin, New York. He owned 100 acres and was building a log cabin on it with his own hands. He and his friends would go there on the weekends to build. My mom and I only visited a couple of times. Maybe even only once. There was no bathroom yet, just an outhouse. But that was fine. 

I loved being out in the woods. I loved cooking on a campfire. 

We walked a path through the woods to a stream on Louie’s property. Louie handed my mom and me each a bota bag, then started filling his. “We can drink this?” I asked, wide-eyed. Louie said we could. 

It was the most delicious water I’d ever tasted. I’d never liked water from the tap. Sometimes it was cloudy and only tolerable with lots of ice. Even then, I’d rather drink juice.

Today, I laugh at that question. Only a human child would have to ask if that water was drinkable. 

Tony’s wife wasn’t the only customer’s wife who’d had an affair with the gardener. I’d heard this story before too. 

Another regular of mine, a general contractor, was always griping that he’d built his dream house in upstate New York, but now his ex-wife was living in it with their former gardener. 

I thought about Tony’s wife’s point of view. She was raising three children, mostly on her own. Her husband was out of town a lot.

I remembered my old boyfriend’s older brother, the commercial director who used to work in LA all the time. James was gone for about two or three weeks a month. That sounds like a lot. But from his point of view, when he was home, he was really home. He was present, fully there, as opposed to other fathers who worked every day and then came home at night tired and not really available.

One day, James' wife told me her point of view. She said that when James came home, he disrupted their routines. Unlike Tony’s wife, James' wife ran the house like a finely tuned machine. When James came home, he messed things up. He disrupted homework routines, bedtime routines, that sort of thing. He’d be home just long enough to destabilize everything. Then he’d go away long enough for her to reestablish patterns. When he returned, the cycle would begin again.

James' wife shared this with me in detail. It enabled me to recognize the pattern when men shared bits of their version of the story. I’d heard this many times.

I thought about Tony’s wife, home alone with the kids, her husband in the sky. And here was this man around the house who was just the opposite.

Present. 

Consistent.

Grounded, literally. 

Maybe he listened to her daily ups and downs with the kids. Maybe he played with them in the yard. Maybe he taught them how to pull weeds or mow the grass. 

Maybe he wasn’t just an employee. Maybe he owned the business. Maybe he ran a busy, lucrative business with lots of wealthy clients. 

Maybe he wasn’t a loser at all. 

Maybe he was a strong man, one who worked with his hands and tended to life. Maybe he nurtured things to vibrant health and protected them from unexpected storms. 

Maybe if he found a bird with a broken wing in the garden, he’d take it home and nurture it back to health. 

Then set it free.