Avg. Saturday Date Night

It was a typical Saturday night in this beautiful, sun-baked, and completely goddamn hopeless armpit they call Tucson. I’m in the last 90-day stretch of my prison sentence here, and I’m feeling… antsy. I told myself I wasn’t after sex. That’s the beautiful, quiet, and completely fraudulent lie every man tells himself right before he puts on a clean shirt. I just wanted to go to this new speakeasy. I wanted some of those bacon-wrapped shrimp I like. I just needed a warm body, a goddamn co-pilot for the evening’s nosedive.

The dating apps out here… Christ. They’re not a “dating pool”; they’re a goddamn toxic swamp. A lineup of the lost, the lonely, and the profoundly, breathtakingly ugly. But I found one. Forty years old. Tall. Dark brown eyes. Lived on the East Side, which is never a good sign. But what the hell.

I told her to meet me in the parking lot. She rolls up in a beat-to-shit Suburban, a real relic. “Car’s broke,” she says. “It’s my dad’s.” A beautiful, perfect, and completely classic opening scene for the tragedy to come. She was tall, nice shape, but with that particular kind of “Tucson” look. Ugly tattoos scattered around like she’d lost a bet with a blind scratcher. Later, she tells me her dad’s best friend gave them to her for free when she was 18. Of course he did.

She’s wearing a white sweater, the kind that exposes the shoulders, kind of attractive in a “trying too hard” sort of way. But she couldn’t make eye contact. A bad sign.

We get into the restaurant. I order her a drink, something strong. The food was good, I got my shrimp, and I started the autopsy. A man has to do his due diligence, doesn’t he?

“So, what’s your story?”

And out it comes. The beautiful, ugly, and completely predictable laundry list of a life lived in the passenger seat of one burning car after another.

She’s forty. She has three kids. Five, seven, and nine. She cleans houses… for an agency. For “very little money.” She’s “going through a divorce,” but the husband, a “druggie” who “lives on the streets,” refuses to sign the papers. Oh, and before that guy? She was living in Mexico with a “cartel guy.”

And after laying out this beautiful, five-car pileup of a life, she looks at me with those sad, brown, and completely honest eyes and says, “I guess I just need to be a better picker of men.”

Christ. I almost choked on my goddamn shrimp. That’s like a skydiver, standing in a field after his chute didn’t open, saying, “I guess I just need to pick a better landing spot.” The beautiful, tragic, and completely hilarious lack of self-awareness was breathtaking.

But I’m a gentleman, in my own fucked-up way. I kept her laughing. We went to the speakeasy. She loved it, of course. She was out of her element, a beautiful, broken little bird in a gilded cage. She had to describe what she wanted, and the bartender, a real artist, made her some pink, frothy thing. She was happy. I was happy. A quiet, successful, and completely fraudulent first act.

We’re walking through town, some DJ at The Congress starts playing some awful, techno-crab-walk bullshit that clears the street. We end up at a dive bar. The final scene. By this time, I’ve stolen a kiss. I’m nursing a beer. I’m calculating the odds. The “no sex” plan is looking a little shaky.

And then her phone rings.

She excuses herself to go to the “bathroom,” which is just a pretty word for “a quiet place to hear the other bomb drop.”

She comes back, and her face has just… collapsed. That nervous, no-eye-contact look from the parking lot is back, but this time it’s got a beautiful, dark, and completely terrified glaze on it.

“He took the kids,” she says, her voice a whisper.

“Who?”

“My husband.” The homeless druggie. The one who won’t sign the papers. “They were at his mom’s house. He went and got them, and now he’s calling Child Protective Services on me… because I’m out with you and not at home.”

And I just… stared. “Wait a minute,” I said. “I thought you were getting full custody?”

“Yeah,” she said, “…after the divorce. We’re not divorced yet.”

A beautiful, ugly, and completely inconvenient little detail.

She was born in Germany, an Army brat, bounced all over the goddamn world, and the music finally stopped here, in this shithole. She told me, with a strange kind of pride, that her kids were “feral,” that the only thing that could control them was an Xbox. This woman wasn’t just a collection of bad decisions; she was a goddamn connoisseur.

And I’m looking at her, and I’m thinking, it’s not just her. It’s this place. It’s Tucson. There’s something in the goddamn water. All the white women here have that same “crack head” aesthetic, that little extra inch of spacing between the eyes. The woman I used to sleep with in Scottsdale, the submissive one, she had it too. It’s a look. The Mexicans are the best-looking ones out here, by a goddamn mile.

I’ve been in this armpit for nine months, and I swear, the dating pool isn’t just a pool; it’s a goddamn lukewarm, shallow swamp of “dead-teen women.” It’s like a strip joint. At night, in the dark, from a distance, with enough booze in you, they look okay. You come back in the daylight? It’s a goddamn horror show. Just trailer-trash, drug-infested, beautiful, ugly, and completely batshit-crazy whack nuts.

So, you ask me what I’m going to do for my last two months in this beautiful, cursed, and completely hopeless town?

I’m retiring from the game. I’m done. I’m going to sit at home and jerk off. It’s cheaper, it’s safer, and it’s a hell of a lot more predictable. Out here, on a simple date, you’ve got a 50/50 shot of catching a new strain of herpes or getting a shiv in your ribs from a homeless, junkie, not-quite-ex-husband.

No, thank you. I’ll take my chances with my own goddamn hand.

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James O

Born behind a Tommy’s Burgers to a mother I had to divorce at thirteen, just to survive. I was homeless in Los Angeles by sixteen, armed with nothing but a backpack full of rage. I clawed my way out through a crooked high school diploma and a failed stint in the Navy that got me ninety days in the brig and a boot back to the street.

I decided the world wasn't going to give me a damn thing, so I took it. I went from the shipyards to drafting rooms to building my own engineering firms. I learned the game, held my ground against the suits, and became a self-made millionaire with an office in Singapore before I was thirty. I chased the American Dream and, for a while, I caught that bastard by the throat.

Then I did the stupidest thing a man can do: I retired at thirty-five. Thought I could buy peace. I built a fortress of money and success on a yuppie ranch in Oregon, a monument to everything I’d survived. But the cage wasn't to keep the world out; it was to keep me in. And the one person I handed the key to, the one I trusted inside my walls? She turned out to be a ghost, wearing the face of the same damn madness I’d spent my whole life trying to outrun.