The Tuesday Challenge

Skyler pushed through the door of The Back Room at 6:40 on a Tuesday, ten minutes early, because showing up late to a first meeting with a man off the internet felt like handing him a win. She was thirty-three and had been through enough first dates to know the small stuff mattered.

She spotted him right away at the bar. Mikey, thirty-four, taller than his photos, wearing a shirt that said he had tried exactly the right amount. He turned his head at the door and their eyes caught for a second. Something in her stomach did a quick little drop, the kind she had not felt in a while, and she thought, well, okay then. The chemistry was not going to be a problem.

"Skyler?" he said, sliding off the stool.

"That's me. You're taller than your pictures."

"You're prettier than yours, so we're even." He gestured at the high-top near the dartboard. "Booth or stool?"

"High-top. I like to be able to escape quickly if you're weird."

He laughed and it was a real laugh, not a polite one. "Fair. I've earned a weird reputation in the chats, I guess."

"You called a burrito a flavor tube. That lives with a person."

They sat and a woman with tired eyes took their orders. Skyler got a pale ale, Mikey got whatever the IPA on tap was, and they clinked glasses without making a thing of it.

"So," he said. "Hair. Do you actually like doing it or is it just a job?"

"I actually like it. People sit in my chair and tell me their whole lives in forty-five minutes. I know who's cheating on who in three zip codes." She took a drink. "What about you, code guy. Do you actually like the computers or is it just a job?"

"I like the solving part. I don't love meetings where eight people discuss whether a button should be blue."

"Is it blue?"

"It was green for two years. Now it's blue. Nobody's happy."

"That's the most relatable thing anyone's ever said to me on a first date, and I want you to know the bar is on the floor."

"Bad dates?" he asked. "Lay one on me."

"Oh, I have inventory. There was the guy who brought his mother."

"To the date?"

"To the date. She ordered for me. Chicken, because she said I looked like a chicken person."

Mikey put his beer down. "No."

"Yes. And she paid, which was somehow worse, because then I felt like I owed them both a thank you card."

"Okay, I can top that. A woman spent forty minutes showing me pictures of her ex's dog. Not her dog. The ex's dog. She still walked it on weekends."

"That's actually kind of sweet in a sad way."

"It would be, except she cried at the end. Over the dog. Then asked if I wanted to split the check by item, like line by line, she had a system."

"Did you order more expensive things because she was paying half?"

"Of course. I got a dessert I didn't even want. I don't even like cheesecake."

Skyler laughed so hard she had to set her glass down. "Okay, we're going to get along horribly, I can tell."

They ate the little basket of pretzels and traded a few more stories, his terrible open mic date, her guy who quizzed her on baseball stats to see if she was "a real fan." It was easy. She kept noticing how easy it was. Two weeks of messages had felt like flirting with a concept. In person he leaned in when she talked and remembered details, like her sister's name, like the town she grew up in.

At some point he glanced at the dartboard on the wall behind them, dark cork with a ring of holes around the bullseye like it had been shot at for decades.

"You play?" he asked.

"I play."

"That was not a confident answer."

"That was an extremely confident answer." She stood and collected the darts from the shelf. "Three darts each, closest to the bull after three rounds buys the next round. Loser also has to admit, out loud, that the winner is better at darts."

"Oh, we're adding speech requirements."

"I'm a hairdresser. I believe in stakes."

He went first. His first dart hit the twenty ring, his second wobbled and stuck low, his third landed just outside the bull. "See, that last one was a statement of intent."

"Uh huh." She shook her arm out, threw. Twenty. Nineteen. Then a dart that landed two inches from the bull. She heard him suck air through his teeth.

Round two he got closer, one dart brushing the wire of the outer bull and bouncing out to the floor, which the whole bar seemed to hear. A guy at the end of the bar said "oof" without turning around.

"That's a bad omen," Mikey said, retrieving it.

"That's a bad throw."

His second round put one dead in the twenty, so close she had to look twice. Then she stepped up, rolled the dart in her fingers the way her old roommate taught her, and let it go. It thunked into the red center and the bar guy said "hey, nice" from his stool.

She turned around slow. "So."

"Nope. One more round. Best of."

"Best of was the original deal. You're amending terms like a middle manager."

"Three darts, winner takes all, loser says the sentence." He was grinning with something competitive under it that she liked a lot. He had seemed so easygoing in the chats. This was better.

He threw first and put two in the twenties and one just outside the ring. Decent. Beatable. She took her time, which she could tell annoyed him, lined up, and put the first dart in the twenty, the second a hair outside the bull, and the third, well. The third she got lucky and she knew it, hit the inner ring off-center, but it counted. Closest wins and closest was hers.

"Say the sentence," she said.

He sighed like a man at a job he didn't love. "Skyler is better at darts than me. And possibly at everything. Unclear. Pending further testing."

"That last part sounded like a compliment and a threat."

"Good. It was both."

They went back to the high-top and he bought the round like a gentleman, two more beers, and they clinked again. The jukebox cycled over to some old song, and the bar had that warm early-evening hum of people pretending Tuesday was fine.

Skyler turned her glass in a slow circle on the coaster and looked at him. Here was the thing she had been turning over for two days. She was competitive in a way her friends teased her about. She kept a list on her phone of new things she had tried, one a month, and this month's slot was empty and it was the twenty-ninth already. And sitting across from this man, she felt safe and interested at the same time, which was a rare combination.

"Okay," she said. "New idea."

"Uh oh."

"Shut up, let me finish." She leaned in on her elbows. "I have a proposal. One new thing. One specific thing neither of us has ever done, we try it tonight, and there are rules."

He set his beer down. "This is either going somewhere very good or very strange and I genuinely can't tell."

"Rules," she said, holding up a finger. "One, we say out loud what the thing is before anything happens, so nobody's surprised. Two, anybody can stop it at any second, no hard feelings, no questions. Three, no expectations past tonight. No follow-up texts we feel weird about, no awkward coffee. We walk in, we do the thing or we don't, we walk out friends who have a story."

"That's a lot of structure for a Tuesday."

"I'm a Capricorn, structure is my whole personality."

"Okay, I'll bite." He was watching her face now, fully, and she could see he was curious and a little excited and trying not to show either. "What's the thing?"

She took a drink, mostly for courage, and put the glass down.

"There's one act I've never done and always been curious about," she said, keeping her voice low, "and I've never trusted anyone enough to just ask for it flat out. But you seem like someone who can follow rules and keep his mouth shut, and honestly you're cute enough that I'd regret not asking."

His eyebrows went up. "Now you have to tell me."

"That's the deal. You agree to the rules first, then I say the thing. All in or nothing."

He drummed his fingers on the table once, twice, thinking, and she watched him decide something.

"All in," he said. "Rules accepted. What's the thing?"

Skyler looked around the bar, at the worn booths and the dartboard and nobody paying them any attention, and leaned in close.

"There's one act I've never done," she said, quiet enough that the guy fiddling with the jukebox couldn't hear it, "and I want to try it with you tonight. I want you to fuck my ass."

Mikey went very still. Then he picked up his beer, took a long drink, and set it down with both hands like it needed steadying.

"Okay," he said. "Wow. Okay. That was not on my bingo card and I mean that in the best possible way."

"You don't have to say yes."

"I know. That's what makes it a good question." He turned his glass a little, matching her habit, and she noticed that and liked it. "Can I be honest about my process here? I need about ninety seconds of staring into the middle distance."

"Take your time." She ate a pretzel. She was calm on the outside and her pulse was doing laps on the inside, but that was fine, that was part of it.

"Okay, process done." He leaned back in. "Yes. I'm in. I've never done it either, for the record, so we'd be two idiots figuring it out together, which honestly sounds better than one expert and one nervous guy."

"That's exactly the spirit I was hoping for."

"But I have questions. Logistics questions. I'm a code guy, I think in logistics."

"Ask."

"Condoms, obviously. And lube. Real lube, not the lotion situation in my bathroom. I