Thirty-Six Questions to Fall in Love

Jen was pretty, mostly just “okay,” as boys said in high school, but high school is a world of competitive friendships and acute cruelty. James didn’t do much better as far as his looks, when he was that same age, when he went by Jimmy. In college, when Jen’s cross-country leanness opened to something more suggestive, she’d had as much sex with men or women, sometimes both, as she’d wanted, for four years. She’d done well enough in New York on the apps, had several relationships she thought would become serious but fizzled to fumes. Some time after a breakup, she was ready to “put herself out there again,” as her therapist, whom she met with online, suggested. Her therapist had taught her, in a single guided meditation session, to rest in stillness. “Stillness” was always there, in the background, behind everything, between breaths, a place of calm. Jen could rest in stillness no matter where she was, who she was with, living a life of plentitude or deficiency. In her best moments alongside the stillness she’d say life was beautiful and always would be. 

James had a long-term girlfriend when he was a teenager. They broke up in college, and since he had enjoyed drunken play and hookups into his mid-twenties, a healthy sex life that would have been considered “slutty” if he was female. He remained average in looks, but above average in height, which gave him an advantage. He only used dating apps that allowed him to list his 6’2” height, so he wouldn’t have to write clever answers to the prompts. He met up with several matches, though the ones he liked and followed up with were following up with someone else, and he couldn’t seem to get any connection to conjugate. Then he met Jen. 

Jen had said on her profile that she was looking for someone to do the “Thirty-Six Questions to Fall in Love” with, and James was interested. People ask things on dates all the time, but never with such intense purpose or direction. He looked up the questions and felt anxiety, wondering what answers Jen might want to hear. He assumed they’d do this at a restaurant or bar where he’d have the help of alcohol, so decided it was a problem he’d solve in real time. 

•

Jen wore a light, black coat over a black blouse, and a yellow scarf tied around her neck, her best outfit—and James immediately knew he was attracted to her. She wasn’t sure what she felt towards James—he seemed murkier and less self-assured standing before her, not much data in itself, and she scanned for more red, yellow and green flags.  James thought Jen seemed older and more threadbare in person, which meant wrinkles near her eyes, a widened face—an intrusive thought and one he felt embarrassed to have, as it seemed unfair, misogynistic, unavoidable. 

“Hi?” James said. Jen was hovering nervously, not quite up at the bar, not quite near the door. James had suggested a popular place the internet had suggested to him for a first date, a place he would have wanted to check out anyways, and the kind of place Jen would have only gone for a friend’s birthday, or a date. “James.” They hugged. Jen felt nervous about the impression she was making. James’ anxieties laid more in the question of whether he was wasting someone’s time. He wanted her time to be worth it as a measure of how valuable he was to women in general. 

Jen ordered a vodka soda, James ordered a mid-ABV beer. He paid and left the tab open. They sat at the bar, the last two seats open. 

“Thanks for meeting up. Where were you coming from?” he asked. Easy questions, easy answers.

“Just coming from home. Yeah.” 

“Ah okay. Same. Took the subway.”

“Well, thank you for not asking me to a bar at the corner of your block.” Jen studied his reaction. Asserting appreciation for a boundary he hadn’t known existed was her play, and if the guy pushed back, she knew it would never be worth it. If he filed the information, she saw it as a positive character trait. 

“So what do you do?” he asked. He didn’t think they would go right into the thirty-six questions.

“I nanny part time,” she said. “And work one day a week at a boutique.”

“Oh, cool,” he said. 

“You?” 

“I do digital storytelling, copywriting for websites,” he said. 

“I thought AI was replacing all that.” She lowered her eyelids, a look that made her look a bit like Marilyn Monroe, at least in the eyes. It usually worked. 

“Shit,” he said, laughing. She smiled at him, and took a sip of her drink, and smiled again when she set it down. This is great, he thought. “I do use AI sometimes. I had to write about this family fun park on Long Island. I was looking up why people like go carts and batting cages. AI told me all about it.”

“What did it say?” 

“Simulate dangerous thrills in a safe environment. Convenience, day trip. Versatile attractions. I copped a lot of language.”

“Bravo,” she said. 

“Have you ever been to a place like that?” he asked.

“I’ve been to Coney Island but didn’t go on the rides, or in the water. I drank one of those nutcracker drinks, though.”

“Oh, that’s a dangerous thrill.”

“World class,” she said, sort of making fun of herself, or maybe him. He wasn’t sure. James thought the date was going well. Jen was relieved she hadn’t seen or heard any red flags so far. 

“I wanted to tell you,” he said. “I was so curious about these thirty-six questions you mentioned on your profile. Is that like, your thing?” She winced a bit and looked away, then scratched her arm, crossing it in front of her.

“Not my thing,” she said. “I haven’t done it in a while, it’s hard to get people to do it.”

“I’m down to try?” James wouldn’t have been able to say why he was willing to do the questions, but the truth was that he found comfort in the structured framing of a date. If the conversation was dull, it wasn’t even fifty percent his fault. Jen sipped her drink, tapping her fingers on the side of the wide glass, her other hand now scrolling on her phone. She held her finger up, signaling she would be ready in just a second.

“Okay, here is question one,” she said, setting her phone on the table. He saw the phone browser was open to a website with a large “Women’s Health” banner. “Okay. One: Given the choice of anyone in the world, whom would you want as a dinner guest?” She narrowed in on him with her eyes, play-acting like it was now more serious than it was. He had looked at the first few questions, and this was the only one he had thought about. 

“Jesus Christ,” he said. “Then I’d know he was actually real, also, in my mind I’m present at the last supper.”

“Wow.” She said. “Sure. Are you Christian, or a cannibal? The body of Christ and all that.” 

“I’m neither,” he said, a little defensively. “I could switch answers to the Buddha, I guess.”

“The Buddha definitely is gonna want to go to White Castle.” There was a White Castle across the street, on the corner. Bright lights on. 

“I’d go with the Buddha to White Castle for our meal together.”

“I would, too,” she said. 

“What’s your answer?”

“Buddha to White Castle,” she said. 

“Hmm, seems like cheating.”

“Okay, last supper then. There’s twelve seats, right?”

“Oh, come on,” he said. “Tell me your answer.”

“Mmm, okay. Meryl Streep.”

Jen liked the verbal sparring and hoped to escalate it as the questions went on. She was in control of him and knew she would be the whole night.

“Okay, fine.”

“Two: Would you like to be famous and in what way?” She sucked the straw of her drink. James noticed she was getting low, and gulped on his beer a few times. 

“Um,” he said, searching his mind. He didn’t do anything that he would ever be famous for, as far as hobbies or talents. “I played baseball in school. It would have been cool to have my own baseball card.” Jen’s reaction showed no enthusiasm. 

“Okay,” she said slowly. James knew this wasn’t good. “That’s a little boring, but okay.”

“Okay, well,” James quickly backpedaled, “I’m famously bad at question two.” He felt a little insulted. It was early; if things went bad maybe he could still make something of the night, even if it was just watching TV at home.  

“Okayyy,” she said, singing it in a surrendered tone, adding some upspeak to seem girlish and inoffensive. “Well, there’s over 30 questions left, babe, so don’t worry.” 

James thought he had her interest locked in at this point, if she wanted to ask them all. If he was Jen, and Jen wasn’t having a good time, he would mention she had to work early the next day, as to have an excuse to politely leave after the first drink. Dating was easy in this way: There was a convention for every out. 

“Before making a phone call, do you ever rehearse what you are going to say?” she asked, in a weird game-show voice.

“Oh, man,” he said. 

“I won’t judge your answers anymore,” she said. 

“I practiced a job interview once,” he said. 

“This question might be a little dated. We as a society aren’t talking on the phone much anymore, are we?”

“I’ve typed out a lot of text drafts.”

“Haha, yes,” she said. “The drafts for sure.”

“What about you?”

“I practice breaking up with people. I have a friend for that. Ryan.”

“Oh,” James said. 

“Ryan’s gay but has a high emotional intelligence for how you straight boys behave.”

“Got it,” James said. She seemed a few moves ahead of him. Jen believed the date was going well. James believed it wasn’t going bad, but he was back where he couldn’t be sure at this point. This would have delighted Jen, because she found comfort in advantage. James enjoyed certainty. 

The bartender stopped in front of them and put down two shot glasses, filled them each about three-quarters, then stepped away. Jen had seen this trick before—bartenders did it whenever two people seemed to be on a first date. 

“We must look tense,” Jen said. They clicked the glasses carefully, then drank. The liquor was rank; Jen didn’t like the taste, and didn’t necessarily like being drunk. Tipsy was okay. James associated the strong taste with nights of oblivion and bad hangovers. He loved being drunk, but tonight he wouldn’t get drunk. He didn’t want to embarrass himself.

“Hey, let me ask you the next question,” he said, reaching for her phone. 

“Okay, Mr. Liquid Courage,” she said. 

“ No password on your phone, interesting.”

“I live alone,” she said. 

“Question four: What would constitute a perfect day for you?” 

Jen rested her head against her balled up fist, propped by her elbow. It would have seemed like a pose if she wasn’t earnestly lost in the question, wondering how much to disclose.

“You know,” she said. “At this point, a perfect day, I wake up, I don’t work, I have coffee in bed. I call my parents. I get groceries, have a good breakfast. I clean up breakfast, clean my kitchen. I clean my apartment a bit. Then a man comes over and helps me put on my fitted sheets, then sits with me while I change the pillowcases and make up the bedding.”

“What do you mean a man?” James asked. He wasn’t sure of the implication.

“Any man. You know, just, categorically. Someone who I want to be there.” James was confused; this perfect day seemed so possible. His pint was empty. He had a two-drink limit on dates, but the shot blotted out that judgment. 

“I could come over and sit there, easily enough. I don’t get what’s so perfect about that. You could have a hundred of these perfect days in a year.” Jen looked up at him. James wasn’t being rude, he believed he was being encouraging. 

“Just to sit there,” she said. “I’m on Hinge after all.” James inferred she didn’t have anyone to come over. 

“What about Ryan, your gay friend?” 

“Wouldn’t work,” she said. 

“Okay, well I could come over,” James said. Jen hesitated, realizing she put herself in this corner, where he would ask. She looked at him again. He felt he was offering something important and valuable and should be rewarded for it.

“Okay,” she said. “Come over…” She opened her phone and looked at the weather app. “Come over in two days. It will be sunny, I want the windows to be open. The sun comes into my room in the afternoon around 5 p.m. Come at 5 p.m.”

•

Jen lived in a great neighborhood, near the subway; it was easy for James to get to. She opened the door in a black cut-off T-shirt and jean shorts. Her hair was tied back. This is Jen, James thought. He thought she looked cute, and they would have made a cute couple. 

She asked him to take his shoes off. Fucking shit, thought James. He didn’t anticipate this custom. His socks were old; they were fine. She gave him a cup of water, walked him through the kitchen, then the slight hall to the bedroom. A thin curtain was parted, the only segregation between any of the rooms. He stood in the doorway and looked at her bed. The mattress was on stands, Tupperware with clothes were stored under the bed. He imagined her happy here, lighting candles, cleaning the fridge, texting. 

“Take this,” she said. She stretched out a thin sheet, so he held one edge. They opened and laid it over the bed. She pulled a comforter out of a laundry bag, which smelled wonderfully of cotton and detergent. They laid it over the bed again. Fairy lights were strung where a headboard could have been. But it was daytime and there was no use for them. 

“Okay,” she said. She pulled out two pillows. “These are only regular pillows. But you can still sit down.” James looked down at his two-tone threadbare socks. Jen shimmied the pillows into the cases, first one, then the other. Then she took out two lacey pillowcases, more showy and elegant than the previous two, which she must have actually used for sleeping. 

“Move to that far side,” she said. “Sit at a slant, half your butt on the bed, do you know what I mean?” James got up and walked to where she pointed, his body at a lean. He could see out of one of the windows that out over the quiet world outside Jen’s apartment: parked cars, ailanthus trees, maybe a bicycle, faint wind, music from somewhere. He would love to live here. If he had allergies, spring and summer would be hell, but he didn’t, and thought for the first time, on that June afternoon, that heaven was a place where you had nothing and wanted nothing. You just sat on the bed, and you had what you wanted. 

“Okay, that’s one,” Jen said. She slapped the cushion with a few pat pops, then opened the second pillowcase, got the last cushion, and began working it inside, gently rocking and shaking it until it slipped down. James watched her do this one. This wasn’t for him, though. She looked at him a few times, like someone referencing a live drawing model, then looked back at what she was doing. When the pillow was all the way in the case, she double stacked the cushions two-by-two. After a small adjustment or two she nodded that it was done. She looked up at James.

“Thank you.” She said it quickly. She saw James was looking at her still and thought to say it more meaningfully. “No, really, thank you.” She sat at the edge of the bed now, on her side. James watched the mattress give a little. Now they were both on it, which suggested to James maybe he had come here hoping for sex, or something more than what they said. 

“Do you want to,” James said, and Jen darted her eyes to meet his, “take a picture of me sitting here?”

“Oh!” she said. She ran her hands over her shorts, but her phone wasn’t handy. “You know, could I just like, lay down for a bit? You can stay sitting there.”

“Oh,” James said. “Are you tired, do you want—”

“No, no,” Jen said quickly. “Just let me lay for a bit.”

“Yeah, okay.” James realized this was a bit stranger than he expected. He cast an eye to see if there was a vibrator or anything suggestive nearby, but there wasn’t. 

Jen swung her legs up on the bed and came to a rest, laying face up, her arms crossed over her chest for warmth. She breathed deeply, in and out. 

He studied her room more closely now that she was distracted. She had some jewelry on a table next to the bed, ear plugs, an ashwagandha tincture, phone charger wires. She lived here. People’s lives. James thought it was a bit sad, in the way that sometimes accidentally seeing inside someone’s private business makes you feel a bit sorry for them. An accent wall opposite the bed was painted a light teal, like the ceiling of Grand Central, but without any of the gold figures. 

James looked back out the window, at the empty rooftops, then up at the huge clouds, a church tower and what looked like the Williamsburgh Savings Bank Tower, and the sunlight beyond. 

Jen’s breathing changed slightly, and James thought she had snuck her hands down her pants after all, but realized she was crying. He didn’t know what to do. He wasn’t good with this. 

“I’m sorry,” she said, when she saw he was looking. “Life is really difficult.”

“Nah,” he said. “Hey, don’t worry about it.” He was in over his depth. “Is there something going on?”

“No, no.” She rapidly composed herself. “That was perfect, thank you. Really, I mean it.” She got up and went to the bathroom down the hall. 

James guessed she must be lonely, and, looking around, saw her bookcase, jewelry tree, photos tacked to the wall. He thought about what she said, and thought that life looked at as a solitary endeavor was pretty hard. His too, depressing—roommates, condiments, trash needing to go out. He heard the chime of a Bluetooth speaker, and some pop music began to play. Jen was on her phone, standing now at the doorway, and her mood had markedly shifted, as if the past twenty minutes hadn’t happened.

“Okay, what can I do for you?” Jen said. Her hair was down and she had refreshed her face. She had brought the glass of water she’d poured him into the room and handed it to him.

“Um,” James said. He had nothing. “Yeah, I don’t know, no real domestic fantasies here.” 

“You know, you didn’t answer the fourth question the other night. What constitutes a perfect day for you?”

“Oh!” James felt relieved. “Well that’s easy, doing something new and exciting.” Such a cliché answer, but it was still true. It wasn’t the answer but the content that made it interesting to him. 

“Well, I don’t think I have anything too new and exciting to offer you here. Chili in your coffee?” She laughed a short, busted laugh.

“Nah,” James said. He felt embarrassed for her having to answer for his perfect day; he didn’t think she was indicted.

“Well, if there is something, you could tell me. But I babysit the kid in an hour so…” Intense relief came over James—he really was worried she would try to peg him, or call a friend over, or something—the unknown. But there wouldn’t be time for that.  

“I don’t know,” James said. “I like authentic experiences. Things that can’t be faked. I realized that writing all that web copy. I was like damn, I should ride go-carts sometime.”

Jen laughed. Her eyes were still wet from the tears, but the overall effect of the flush was sympathetic and attractive.   

“Well, thanks for letting me in on your perfect day,” he said.

“Oh, all the thanks to you. You’re giving twenty-something guys not the absolute worst representation. My opinion of them has gone up from ‘terrible’ to just ‘pretty bad.’”

“That’s a crazy compliment,” James said, in good humor.  He didn’t know her age. His settings on the app weren’t firm, so she could have been—he didn’t know. “It’s bad to ask someone how old they are, right?” 

“Yeah, bad. But I can let you in on the secret, I’m thirty-five.”

“Oh.” James felt a panic coming over, only because he hadn’t known, or realized, and might have said all kinds of offensive things. He had never spent time with a woman this old. He had the good sense not to say anything else. “Nice.”

“Nice,” she mocked. “You know what, James? Have you ever been peed on?”

“Hm, peed on?”

“Yeah like, in a cute, intimate way, like, ‘My beloved peed on me, it was intimate and cute.’”

“Yeah, no, no, not that I know of.” James’ mind was racing. He saw himself from a bird’s eye view, in a strange neighborhood, in a stranger’s apartment, with this twist ending to the perfect day.  “That’s part of your perfect day?”

“Oh,” she replied, suddenly becoming repulsed. “God, no.” She waved it off. “You seem heavy on authentic experiences, new things. Experiences.” James processed this. He looked at her from this renewed perspective. She was a beautiful woman, he would have fucked her, and it seemed now she knew something he wanted that he hadn’t even been aware of. 

“But we just made up the bed.”

“Oh, sweetie,” she said. “We do that in the bathroom. You lay down and I squat and go on you.”

That’s just how they did it. James hadn’t been naked in front of someone like this while sober for as long as he could remember. Jen felt comfortable and had hardly any hesitation. She left her shirt on, directing James to get into the tub, too small for him to stretch out, and lay back. He folded his hands behind his head as she carefully stepped over him. She squatted down. He  saw a triangle of public hair and felt himself starting to get erect, but she wasn’t touching him, just hovering. 

“Your pussy, I can smell it.”

“Yeah?” she said, not really asking.

“It smells amazing.”

Jen didn’t respond or acknowledge him, hoping he’d get that that wasn’t what this was about. 

“This isn’t stage fright, I promise.” James realized she couldn’t pee. He had absolutely no script for this. “Well this is no ayahuasca trip to Peru, or bachelor’s in Vegas, but it’s something at least.” 

“Yes,” he said. “Yes, it is.”

“Wait,” she said. “Something’s happening!” A warm trickle of pee rolled down his belly, down his side, into the tub. It lasted for a few seconds. “That’s all I can do, sorry.”

•

Jen walked him out downstairs and unlocked the door to her building. The goodbye was worse than awkward, due to James, who was wrapped up in his own confused thoughts. “Can I hug you?” she finally asked. And they did. She seemed unphased by the entire afternoon. James was rattled, activated, taking his first breath in a new world. 

When he got home, he saw they were no longer matched on the dating app where they had done all their communicating—Jen had deleted him. That was that. Jen and James never saw or spoke of each other again.   

Ben Fama is the author of the poetry collections Fantasy (Ugly Duckling Presse, 2015) and Deathwish (Newest York, 2018). His debut novel If I Close My Eyes was published by SARKA in 2023. He is the editor of Wonder Books and lives in New York City.