The Rooftop Wager

The heatwave had been sitting on the city for nine days by the time I gave up on dignity. I was twenty-nine, three years out of law school, and I was lying on my kitchen floor in shorts and a sports bra with a box fan aimed at my face, reading the same paragraph of a discovery motion for the fourth time. The paragraph was not that hard. The heat was just winning.

My apartment had a fire escape, which the listing had called "outdoor living space," and which was actually an iron balcony the size of a welcome mat with a view of a brick wall and, if you leaned out, a slice of the harbor. In weather like this the metal held the day's heat until midnight. I sat out there anyway, most nights, with a beer and my phone, and usually Sebastian was on the other end of the phone, which was its own kind of problem.

Sebastian Crowley was twenty-eight, an architect, and my best friend for three years, ever since a law school mixer where neither of us knew anybody and we ended up arguing about whether Brutalism was a style or a personality disorder. I don't even remember who won. I remember he was funny and he paid attention and I thought, well, here's a person, and then I thought, and oh no, here's exactly the person, and I have mostly managed not to think the second thought since.

He saw me the way you see a good recliner. Reliable. There when you sit down. Never once in three years had he looked at me and seen anything you'd take out of the house. He talked to me about other women. He asked my advice about their texts. Once he asked whether a dress made a date look "approachable," and I said yes, and I went home and ate cereal standing up at the counter like a man in a sitcom about divorce.

I want to be fair to him. He was never cruel. He just had me sorted into a box labeled Cassie, Friend, Do Not Open, and the label had been on there so long neither of us questioned it. Meanwhile the box was sitting in the sun and the contents were getting warm, if you follow me, and this summer everyone in the city was getting warm whether they liked it or not.

* * *

That Thursday the temperature hit ninety-six and stayed there past sundown, so I was on the fire escape at ten with a beer sweating in my hand and my feet up on the railing, and Sebastian was climbing up the ladder because his apartment had no cross-breeze and he had decided years ago that my fire escape was communal property.

"I brought chips," he said, hauling himself over the rail. He was in shorts and a wrinkled shirt and he looked like every summer I'd ever had.

"You're a saint. Sit anywhere that isn't my feet."

He sat against the opposite rail and we ate chips and complained about the heat, which is what people in this city do from June to September instead of small talk. Then his phone buzzed and he glanced at it and did the small smile he does, and I knew before he said it.

"Date?" I asked.

"Yeah. Saturday. That woman from the climbing gym."

"The one who sent you the photo of her cat?"

"That's the one." He typed something back. "Cute cat. Decent person. Low effort, which is what I'm after right now."

I took a sip of beer and looked out at the brick wall and asked the question I'd been sitting on for about a month. "Do you ever get tired of it? The parade?"

"It's not a parade. It's like six people a year, spread out." He shrugged. "It works. Nobody gets hurt. Alina and I ended fine, we still grab drinks when she's working."

Alina Clinton, twenty-six, bartends at a rooftop place called The Seventh, dated Sebastian for about two months two years back, and remained on such friendly terms with him that it genuinely seemed to cost her nothing. I had decided long ago that Alina was either emotionally enlightened or a robot, and I had not ruled anything out.

"Sure," I said. "It works. You date like a man ordering takeout."

"What's wrong with takeout?"

"Nothing, if you're hungry. But you're thirty, Sebastian. Twenty-eight. Whatever. You're old enough that the takeout thing should be boring you by now, and it doesn't, and I think that's because you never actually sit down at the table."

He looked at me over his beer. "Is this the talk? Are we doing the talk?"

"We're not doing any talk. I'm making an observation."

"You're doing the thing where you psychoanalyze me because you finished a brief and you're feeling powerful."

That stung, mostly because it was a little true, and I took another drink to cover it. Below us somebody's window unit wheezed. Somewhere down the block a car alarm went off, thought about it, and gave up. I picked at the label on my bottle.

"Fine," I said. "You want an observation? Here's one. You date the way you do because it's easy, and anything with actual stakes, you avoid. Work, dating, whatever. You design buildings you'll never have to defend in a public hearing."

"That's not fair. That's literally my job, defending them."

"You know what I mean."

He was quiet for a second, chewing a chip. "Okay, what's this really about? You've been sitting on something all week. You get a line between your eyebrows."

"I don't get a line."

"You absolutely get a line. Right there." He pointed at his own forehead with a chip.

And I don't know, it was ten o'clock on a fire escape that was nine hundred degrees and I'd had two beers and nine days of heat and three years, at that point, of sitting in the friend box with the lid on, and something in me just tipped over. So I said the thing. I should have said a lot of other things, but the thing I said was this:

"I bet you I can make you jealous in a week."

He blinked. "Jealous."

"Jealous."

"Of what? Of who?"

"Of whoever I decide to use. Doesn't matter. I bet I can do it in seven days."

"Why would I get jealous? You're my friend. You can date whoever you want. I would be happy for you."

"You say that," I said, "with the confidence of a man who has never once considered the alternative."

"Cassie." He set his beer down on the iron between us, and it clinked, and the sound seemed loud after all that quiet. "What is actually going on with you right now?"

And I looked at him, sitting there with his wrinkled shirt and his open face, completely sincere, completely certain that he would be happy for me, and I understood that he meant it, that he truly, honestly believed there was nothing in the world that could make him jealous over Cassie Kepler, and that certainty made me want to break something. So I laughed instead, a bad laugh, a little too loud.

"Nothing's going on. I'm messing with you. It's the heat." I waved a hand. "Forget the bet."

"You just said a bet."

"I unsaid it. It's ninety-six degrees at ten p.m., nobody can be held responsible for what they say out here."

He didn't laugh. He studied me, and for the first time all summer he looked like he was actually seeing something instead of confirming that everything was in its place. "You're serious," he said slowly. "You actually want to do this bet."

I should have dropped it. Any competent adult would have dropped it. Instead I heard myself say, "Fine, yes, let's do it. Seven days. If I can make you jealous before next Thursday, you admit it out loud, that the takeout thing isn't working for you and you're scared of anything with stakes."

"And if you can't?"

"Then I'll drop it. All of it. Whatever this is, whatever you think the line between my eyebrows means, I drop it forever and we go back to chips and dates with climbing women and I never say another word about your love life."

He thought about it. I watched him think about it, which took about four seconds, because Sebastian has never once believed he could lose a bet he didn't understand.

"Deal," he said, and put out his hand.

We shook on it. His hand was warm and rough from the rail, and mine was a little damp, and I held on maybe half a second longer than a handshake requires, testing him, and he noticed nothing. Of course he noticed nothing.

"So who's the target?" he asked, settling back, already amused, already treating it as a game. "You going to download one of the apps?"

"I don't need an app," I said. "I have Ron."

The smile changed on his face. Not much. Just at the corners. "Ron Bartholomew? From your firm? The guy who says 'circling back' in every sentence?"

"He's not that bad."

"Cassie. He wears a tie on casual Friday. He called a paralegal 'sport' in front of a partner."

"He's also genuinely nice to me and he asked me to get drinks two weeks ago and I said I was busy, because I was being an idiot about something. So I'm going to un-busy myself." I took a drink. "And you're going to watch it happen, and we're going to find out what you're made of."

"Ron," Sebastian said again, like the word needed a second pass. "Unbelievable."

"Seven days," I said, and toasted him with my bottle, and he clinked it back, and if there had been even one flake of jealousy in him I'd have sworn I saw it right then. But he just grinned and reached for the chips, and said the words I'd be replaying for the next week.

"This is going to be fun," he said. "For me."

Friday morning I put on the good blouse. Not the nice one, the good one, the one that does things at the collar that HR would call unremarkable and everyone else calls otherwise. I put it on with intent, which is not something I'd done since my second interview, and I checked myself in the break room mirror twice before ten.

Ron found me at my desk at 11:40 with two coffees, which he does anyway, which is part of the problem. He's thirty-two, has a jaw like an ad for something, and says circling back roughly nine times a day. I have spent a year finding this annoying. I now needed to find it charming for seven days. Acting, it turns out, is exhausting.

"Any plans for lunch?" he asked, setting my cup down.

"I was going to grab something near the subway, actually."

"Want company?"

And here is the thing about Ron. He asked. He always asks. He asked two weeks ago about drinks and took no for an answer with actual grace, and then did not make it weird, which is more than I can say for most of the legal profession. Sebastian's impression of him was formed entirely at a holiday party and one deposition. I decided to hold that thought for later examination.

"I'd like that," I said, and smiled the smile from the blouse.

We walked to the subway the long way, the way that goes past the corner with the flower cart, and Ron talked about his weekend plans and I laughed at the right intervals and let my shoulder bump his once on a crowded corner. Once. I'm a lawyer, not a monster. He noticed the bump. I could tell because he stopped talking mid-sentence about his fantasy football league and had to restart the sentence from the top.

At the subway steps he hesitated, and I watched him decide whether to ask, and I saved him the trouble.

"Hey, I'm going to The Seventh tonight with a friend. Rooftop bar. You should come."

"Yeah?" He brightened in a way I pretended not to find endearing. "Yeah, okay. Seven?"

"Seven."

I texted Sebastian from the train platform. A photo, me and Ron, Ron's tie slightly loosened because he'd loosened it for lunch like a man living dangerously, both of us holding coffee cups like they were celebratory. I captioned it: day one.

He replied in under a minute. "He's wearing a tie in the photo. On a Friday." Then: "This is going to be fun. For me." The exact words from the fire escape, repeated, like a man reading lines off a card. I stared at the second text for two blocks and could not tell what it meant, which I decided was a win.

* * *

The Seventh is four floors up on a building that used to be a shipping office, and it has string lights and a wind problem and Alina Clinton behind the bar. Alina is twenty-six, has known me since before she knew Sebastian, and takes one look at my blouse and says, "Oh, we're doing something tonight."

"We're doing a bet," I said.

"Ron's your opening move?" She set down a water she hadn't asked me if I wanted. "Bold. Not good, but bold."

"You knew about Ron?"

"Cassie. He comes here on Thursdays. He tips fine and he talks about a girl at his firm who he thinks doesn't like him." She slid the water closer. "Also I dated Sebastian for two months. I know what a proxy war looks like."

I loved Alina. I should say that plainly, because it matters later. She was the only person in this whole mess who knew every piece of it and thought the whole thing was stupid, and she told me so, and brought me a beer anyway.

Ron arrived at seven. He'd changed shirts, which I noticed, and worn a different tie, which I noticed harder. We got a table at the rail, the good side, harbor side, and he talked and I laughed and at some point his hand rested on the rail about an inch from mine, and I let it, and I posted a second photo, the two of us against the sunset, Ron grinning like someone who had won something he did not know the rules of.

I captioned that one nothing. Let it breathe.

Sebastian did not reply. I checked twice over the rim of my glass. Read nothing, delivered, no dots. Fine. Good, even. That was the point, the silence, the jealousy marinating in the dark somewhere across town.

At eight forty, Alina set a second beer down at our table without being asked, and I looked up, and it wasn't for Ron. It was for the man standing three feet behind Ron with his hands in his pockets, wearing the wrinkled shirt from last night, looking like he'd walked here, which later I confirmed he had, in the heat, ten days into a heatwave, four miles by his own admission.

"Cassie," Sebastian said.

"How did you even know we were here?"

"Your story. Your location tag. You've never used the location tag in your life." He said it flat, no joke in it, which was somehow worse than a joke. "Hey, Ron, right? Sebastian. We met at the holiday thing."

"Right, yeah, Cassie's told me about you," Ron said, and stood, and put his hand out, and they shook, and I watched two men who each thought the other was a prop perform a handshake at the correct level of firmness. Then Sebastian looked at me and tilted his head toward the bar, and it wasn't a question.

Alina, wiping a glass, did not even pretend she wasn't watching.

"I'm working a bet," I said when we got to the far end.

"You're working Ron." He kept his voice low. The bar noise did the rest. "Cassie, the bet is stupid."

"You agreed to the bet."

"I agreed because I thought you were venting. I thought by Friday you'd have forgotten it. This isn't forgetting it. You're doing ops. You used a location tag. You smiled at me in a photo I've seen you take forty times and never post."

"He's nice to me."

"Ron called a paralegal sport in front of Miriam."

"Once. Months ago."

"He circles back, Cassie."

"And what if he does?" I set my bottle down harder than the argument deserved. "What if I date a man who circles back and wears a tie on the wrong day and is, actually, when you subtract your two data points, a good person? What happens to you