The Boyfriend Bet

By the time I got to the bar, I had already decided that my date with Mark counted as a public service. I had spent two hours listening to him explain how he was “between things,” which turned out to mean between jobs, between apartments, and apparently between the point of ordering food and the point of admitting he had no intention of paying for it.

Ethan was at the end of the booth with a beer and a basket of fries. He took one look at my face and pushed the basket toward me.

“That bad?”

“He asked if I knew anyone hiring.”

“For what?”

“He didn’t specify. I think he was open to a broad range of opportunities.”

Ethan laughed. He had been doing that for four years, usually at the right time and rarely in a way that made me want to throw a drink at him. I slid into the booth and stole a fry.

“Did you at least get dinner?” he asked.

“I got half a burger. He said he wasn’t hungry, then ate most of mine while telling me about his ‘creative process.’”

“That sounds like a date.”

“It was definitely an event that happened to me.”

He leaned back, pleased with himself for a joke I had basically handed him. Ethan was tall enough that the booth looked slightly undersized around him. His brown hair was still damp at the edges from the cold outside, and he’d taken off his jacket and folded it beside him. He’d come straight from work, judging by the button-down shirt and the loosened collar.

I pulled off my own coat and draped it beside me. My feet hurt. I’d been on them since noon, and there was a thin line of restaurant stress still lodged between my shoulders. A drink and Ethan’s fries were the closest I was getting to a recovery plan.

“I have to ask,” he said. “What did you think the creative process was going to produce?”

“A second date, at the time.”

“You said yes to a second date?”

“I said I’d think about it. He heard yes. Men are generous with their interpretations.”

“You could try being clearer.”

“I could also try being less tired, but we all have our limits.”

He gave me a look that said he’d been waiting to have this conversation since I texted him from the sidewalk. It was a familiar look. Ethan had the conversational patience of a man who liked being right and didn’t mind waiting for the evidence to catch up.

“Okay,” I said. “Let’s hear it.”

“Hear what?”

“The theory you’re holding in your face.”

“I don’t have a theory.”

“You’re making your theory face.”

“That’s just my face.”

“It’s not. Your face is usually more annoying.”

He took a sip of beer. “You keep saying there are no decent men left, but I don’t think that’s the actual problem.”

“Here we go.”

“I think you choose badly.”

I reached for another fry, mostly to give myself a second. “That’s a very confident thing to say for someone who has watched me date exactly three men.”

“Four.”

“Who was four?”

“The guy who brought a guitar to a first date.”

“He was a musician.”

“He was a guy who brought a guitar to a first date.”

“He said there might be a piano at the restaurant.”

“There was not.”

“No, there was not.”

Ethan’s smile widened. “You’re proving my point.”

“Your point is that I’ve had dates with men who were bad at dates. That’s not a diagnosis.”

“The one who told you he was ‘not a labels person’ after you’d been seeing him for six weeks?”

“He was very clear about it.”

“After six weeks.”

“I said he was bad at communicating.”

“And the one who vanished for three days every time he had a work trip?”

“He was a consultant. They travel.”

“He lived in Denver.”

“He was consulting remotely.”

“Sabrina.”

“What? I’m not defending him. I’m explaining the situation.”

“That’s usually how defending starts.”

I leaned back against the booth. I could hear the bar around us: glasses being set down, the low scrape of chairs, an argument about the Bears at another table. The window beside us reflected the room more clearly than the street outside, already dark before eight. October in Chicago had made an early evening of the day and seemed unlikely to apologize.

“Fine,” I said. “Maybe I have made a few questionable choices.”

“A few?”

“I’m trying to keep the conversation constructive.”

“You tend to like men who make you work for basic information.”

“I like interesting men.”

“You like a mystery.”

“Those are not mutually exclusive.”

“They’re also not the same thing.”

There was no edge in his voice. That was part of what made it hard to dismiss. Ethan wasn’t trying to win an argument for the pleasure of watching me lose. He was honestly amused by my dating history, and he did think I could do better. He’d watched me make excuses for men in real time, then heard me tell the story later as if the ending had surprised me.

I still didn’t like how certain he sounded.

“And what would you know about my type?” I asked. “You’ve been single for months and you swipe like you’re reviewing restaurant applicants.”

“I’m selective.”

“You’re lazy.”

“I’m efficient.”

“You once rejected a woman because her profile said she liked brunch.”

“It said brunch was her personality.”

“That’s a real thing people enjoy.”

“I’m aware. I’m not trying to date the entire city.”

“Neither am I. I’m trying to find one person who can get through a meal without making it about himself.”

“Then stop choosing people who make a good first impression and not much else.”

I paused with a fry halfway to my mouth. “I don’t choose people based on first impressions.”

His eyebrows went up.

“I choose people based on multiple impressions,” I amended. “The first one, and then several increasingly disappointing ones.”

“That’s what I’m saying.”

“No, you’re saying I have terrible taste.”

“You have a very consistent taste.”

“That sounded worse.”

“It’s not supposed to be an insult.”

“Then you should work on delivery.”

He reached for a fry. “You’re attracted to the guy who’s charming and just out of reach. Then you spend six weeks trying to figure out whether he’s interested, instead of asking why he keeps making it hard to tell.”

“You’re making it sound like I have a type because I’m defective.”

“I didn’t say that.”

“You implied it with your whole sales pitch.”

“I’m saying you pick men who make you guess.”

“Sometimes guessing is part of dating.”

“Sometimes it’s just guessing.”

I looked at him over my glass. “You’ve been saving that one?”

“No. It came to me just now.”

“It shows.”

He smiled, unbothered. “You asked.”

“I did not.”

We fell quiet while a server squeezed past the end of our booth. Ethan moved his glass in without looking, making room, then shifted his elbow so I could set my coat more comfortably. Small adjustments, automatic. We’d had enough dinners and drinks over the years that we had stopped needing to negotiate table space.

I picked up the menu, though I already knew I wanted the grilled cheese. “If my taste is so bad, why don’t you prove it?”

“How?”

“Pick someone. Someone normal. Someone you think I’d actually like. I’ll go out with him.”

“You want me to set you up?”

“I want you to defend your argument with evidence.”

“You know this is a terrible way to choose a date.”

“That’s rich coming from the man who thinks app profiles are a reliable personality test.”

“I don’t think they’re reliable. I think they’re useful.”

“Then use them. Find me a decent man. If you’re right, I’ll admit it.”

“And if I’m wrong?”

“You can admit that too.”

He glanced toward the ceiling like he was considering a contract term. “How many chances do I get?”

“One.”

“That’s not enough data.”

“You get one man, one date. I’m not running a clinical trial.”

“You’re the one proposing an experiment.”

“I’m proposing that you stop being smug about my personal life until you’ve done something useful with your theory.”

“I’m not smug.”

“You have been smug since the guitar.”

“The guitar was hard to ignore.”

I closed the menu. “So? Prove it.”

He set his beer down. For once, his smile went away long enough for me to see he was actually thinking about it. I didn’t need him to make a speech. The challenge was mostly a way to keep him from treating my dates like an ongoing comedy special.

“Okay,” he said. “I’ll prove it.”

I took a drink. “Good. Because if you set me up with a man who calls himself an entrepreneur, I’m billing you for the evening.”

“That seems fair.”

“And I get to judge your performance.”

“You do that anyway.”

“Now it’ll be official.”

“Fine.” He picked up a fry. “We’ll make it official.”

I watched him eat it, waiting for the qualification. There wasn’t one. Ethan had accepted, and suddenly my dating history had become a project he could take personally.