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Jack never delivered his drawings to Pulitzer. He had only been taken on because of the point it made to the governor, not because Pulitzer truly wanted to interact every week.
That meant that once a week, Jack Kelly would come to the office and drop the political cartoons off with you to be moved down the production line. As the secretary of one of the richest men in the city - maybe the country - you dealt with a lot of people. Businessmen, the unemployed, important people who needed to be taken down a peg before a meeting - you met them all. Jack was probably your favorite, and it had everything to do with the fact that he was one of the only people who had managed to take Pulitzer down a peg instead.
He had a funny habit of showing you the drawings - something none of the other artists had ever done.
“What’s the point of making a point if nobody is listening?” he had asked, confused, the first time you asked him why he showed you.
“Everybody sees these,” you told him. “It’ll be printed in a few days. Why do you show me earlier?”
His eyes had narrowed, perplexed, but there was something pleasant in it too. “Because I want the opinion of someone who doesn’t have to like it.”
You may not have had to like his work, but you always did. He drew something real, and that made the rest of the world feel fake in comparison. The world looked like smokescreens when Jack Kelly drew, and the pain that came with seeing it was worth the clarity.
Jack’s stomach growled, and the ferocity of it made you raise your eyebrows.
“Mr. Kelly, did you skip breakfast?”
“You can’t skip a meal you don’t eat,” he replied, and set to filling out paperwork permitting the World to release his cartoon.
“You need to eat,” you said, surprised. “You’re starving.”
“I’s saving my money,” he said. His good-natured face closed off, leaving a charming, if impersonal, young man. “I want to buy my own place, but it turns out places ain’t cheap.”
You couldn’t imagine giving up one need to permit another. You couldn’t imagine telling him so, so you didn’t. You pulled your lunch bag out from under your desk, and handed him an apple.
“I can’t take this,” he said.
“Liar.” You pushed it closer, nearly into his chest. “You can, and you will. I have more to eat, and I ate breakfast. I’m at a decided advantage.”
He reluctantly took it, smiling at the savage crunch it gave when he took a bite. “Levelling the playing field?”
“It’s no fun talking to people who can’t keep up. I expect the best from you, Mr. Kelly.”
“Jack,” he said. “We have to level every aspect.”
“Y/N,” you said, and immediately felt foolish. You were wearing a nametag. He had known your name for ages.
“I won’t be taking your food next time.” Jack ate the apple to its core, nipping it as close to the center as possible.
“Because you’ll be eating your own beforehand? I should hope so.”
He smiled ruefully, but the next time he dropped by he swore that his immediate needs had been covered.
You missed a day of work, so sick with the flu that your parents forced you to stay home. When you went back the next day, there was a scrap of paper on your desk.
“Get well soon,” the paper read. Vines of flowers swirled around the margins of the paper, as though the writer had added them as an afterthought. If the handwriting hadn’t given it away, you would have known Jack Kelly’s artistry anywhere.
You carefully pressed the page into your bag so you could pin it on your bedroom wall.
“Why do you work here?” Jack leaned against your table, running his finger along the length of a pencil that you had pushed aside.
“Same reason as you,” you said. “To make a living.”
“Oh, I don’t work here,” he said firmly. “I work for Pulitzer, but I don’t work here. I’m a Newsie.” The distinction fell flat for you, but it was of the utmost importance to him.
“Still? Even now that you have stuff published in the paper?”
“Of course,” he said. He had taken to scribbling trees in the margins of a scrap piece of paper. “The world didn’t stop when the strike did. We’s still working every morning, bright and early.”
“But you don’t have to,” you pointed out. “You have another source of income.”
He shrugged, tossing a meaningless smile your way. “Things happen. Hitting rock bottom on the way out is worse than resting there.”
“Mr. Kelly.” Pulitzer’s voice seeped out of the office like an infection. “If you insist upon distracting my secretary, the least you could do is get work done.”
You gave Jack a pencil and paper, but he didn’t get work done. He drew trees.
(“They’re from California, Y/N. Don’t look at me like that—if you don’t know what the trees there look like, you can’t judge mine.”)
He drew goblins in the sewers.
(“No, they don’t represent anything. Wouldn’t it be neat if they really were down there?”
“I’m pretty sure they are, based on the way you smell.”
“I take it back. These goblins are mean spirited secretaries.”)
He wrote jokes for you, scribbling more flowers in the margins. You hung all of them up at home, ignoring the way your parents side-eyed the steadily depleting wall space.
“Any Valentine’s Day plans?” You scribbled addresses on envelopes for Pulitzer, giving Jack fleeting looks while you waited for his answer.
“Nope.”
“No girls you want to impress?” You grinned at him, light and teasing. “No big dates, or proposals to plan?”
You knew, of course, that Jack wasn’t seeing anybody. You knew that he had no plans for the holiday. You only asked because you expected him to joke back; you hadn’t anticipated his solemn head shake.
“I’s never getting married,” he said matter-of-factly.
“No?” You tried to imagine a Jack Kelly that didn’t want to settle down with somebody, and this wasn’t him. Your Jack loved recklessly, madly, endlessly. Perhaps there was a universe where he ended up alone, wonderfully so, but yours surely ended with him growing old with somebody. Wanting to, at least.
“Never,” he repeated. “I don’t want to ever get married.”
“Huh,” you said, good mood spoiled somewhat. “I wouldn’t have thought it of you.”
He shrugged, leaning his forearms against your desk. “I’ve had a lot of time to think it over, and it’s the only good ending I ever imagine for myself.”
It didn’t sound that good to you, but maybe that had more to do with your future than with his.
The newest addition to your wall art was different—it was in color. Jack had used some of Medda’s paint to give you a paper-sized sunset, and it made your heart twist into knots every time you looked at it.
“That’s quite the collection,” your father said, voice mellow with careful disinterest. “Who’s drawing all of it?”
“A friend from work.”
“Some friend,” he said.
You shrugged, grinning sheepishly. Some friend, indeed.
“When are you getting out of here?” Jack blew at a spare piece of paper, grinning when you clapped a hand over it to keep it from escaping.
“Five,” you said. “You know that.”
“No, I mean out of here entirely. You don’t plan on being a secretary forever, do you?”
You considered. “I guess not. Maybe if I get married I’ll stay home with kids.”
His grin soured a little, and he flicked at your pencil to send it flying. “Huh.”
“Can you really judge?” You rose one brow at Jack, somehow not surprised at all. “I’ll be a stay at home mom. You’ll be single forever, working low-end jobs because you’re worried something higher end won’t work out.”
Jack gave a bitter laugh. “Don’t say it like that. We all have our crosses to bear, right?”
“And yours is squandering potential,” you shot back. “You could have anything you wanted, and I think you know it. You could have a family if you wanted one. You could quit being a Newsie.”
“There’s no quitting,” he scoffed. “There’s only aging out.”
“What’s the difference?”
Jack thoughtfully scrounged through his pockets for a quarter, running his fingertips over the curve of it. “We don’t - there isn’t a future in selling papers. You don’t quit because you want to; you quit because nobody buys from adults. Kids age out, and then they’re left cold and alone in a city that doesn’t want them.”
“I want them,” you said, and the smile he gave you was evidence enough that you had only given him a half truth. “Anyway, that doesn’t explain why you don’t take a chance. Isn’t scraping by worth it if you love what you do?”
“No money, no education, no training in a trade.” Jack flipped the coin and watched it sail high above his head. He caught it with a snap. “Say I marry a girl. Have a kid, maybe. That kid’ll have to sell papers, same as me, just because I can’t support the folks relying on me.”
You watched him flip his coin. He was right. Most people raised in the gutter don’t pull themselves out. That might be fine, if he was the only person who was living on his wages, but if he had others relying on him—
“What if you could be sure of it? That you’d be able to support them, make them happy, all of it.”
“What of it?”
“Would you get married, then?” It was too direct a question, and you both knew it. It had been weeks since the marriage talk. It had been weeks since you should have been imagining Jack with a blushing bride, standing at an alter. Even so, it felt like the question carried weight.
“Maybe,” he allowed. “If I found the right person, you know.”
You smiled then, though you weren’t feeling particularly happy. “You lied. You said that you didn’t ever want to get married, and that’s not true. You want to get married; you just don’t think that you should.”
“Is there a difference?”
The next time he flipped the coin, your hand shot out and caught it before he had the chance. You grinned when you handed it back, his rough hands scraping your smooth ones. “It makes all the difference.”
It was you, this time, giving a drawing. It was nothing good, nothing like he could make, but he loved the flowers nonetheless. You didn’t know it, but he kept it in a box of his most prized possessions.
“‘M thinking of talking to Pulitzer about doing more drawings for the paper,” Jack said, chewing the last of a sandwich.
The two of you were sitting on a bench for your lunch break. He’d never joined you before, but that was as much your fault as it was his. You could always have invited him. You had been chewing a bite of apple, but you paused to look at him. “Really? Do you have time to do more?”
“I’s quitting with the whole Newsie thing soon, I think. Once I get things squared away for me to leave.” He didn’t look at you when he said it, not directly, but you could feel him watching out of the corner of his eye.
You twisted the stem of the apple with more focus than was necessary. “That seems like a risk.”
“Well, you know, sometimes you have to be willing to scrape by for things you love.”
You grinned. “Changing some future plans?”
“A few,” he said. He said nothing more about the future, opting instead to tell you about the first time he saw Bowery performers in their costumes.
A few changes, he’d said. More than one thing. It hadn’t seemed like he had much mapped out, so there were only so many changes he could make. It was difficult not to let your imagination run away with you.
The next time a young man came to the office, it wasn’t the one you were expecting. He came to the desk, polite as can be, and gave the room a cursory glance.
“Things look pretty much the same as last time I came,” he said, thoughtful.
You plastered on your most professional smile. “Can I help you?”
“You weren’t here last time I came,” he added. He smiled back. “I’m here to drop a cartoon off for Jack Kelly. He can’t make it today.”
“Is he okay?”
The boy shrugged. “Sure. He’s busy handling an issue with some of the guys. One of them lost his glasses, but we all know one of the other guys took them as a joke. Jack’s figuring out who.”
Jack had told you about his boys before, and that sounded exactly how you would expect them to act. He had drawn you quick sketches of the Lodge before, lines sharp enough for you to be able to picture the place. You liked imagining him there, but you were disappointed that he hadn’t come.
“Tell him that Y/N says hello,” you said. You put the cartoon in a folder to give Pulitzer, not wanting to examine it in front of a stranger.
The boy grinned. “You’re Y/N. That seems about right.”
“What do you mean?”
“He talks about you all the time. I swear,” the boy said, “he wouldn’t shut up about you if he died.”
The ball of happiness that grew in your chest was too big to adequately express. All you could do was smile, but that seemed like enough for the boy.
He held out a hand. “I’m Davey Jacobs. It’s really good to meet you.”
“He’s talked about you,” you said. His hand was soft when you shook it, but the shake was firm. “All good things.”
“Doubtful.” He glanced at a clock on the wall and grimaced. “I have to go. Maybe I’ll see you around more.”
“Do you think Jack is going to need you to drop things off more?”
“No,” Davey said. “But I wouldn’t be surprised if he started bringing you around.”
“Jack Kelly,” you said.
“Y/N,” he said. He smiled, crooked and unassuming. “You’s in a good mood.”
You weren’t sure what you were, exactly. You were nervous. You were hopeful. You were happy, as usual, to see Jack. Maybe all of that did add up to a good mood, in a weird way.
“So, I met Davey the other day,” you said.
Jack’s smile grew. “And?”
“He was really nice.”
“He’s never been nice to me.” Jack grabbed one of your pencils and started scribbling a building on the back of a receipt. “He must like you.”
You leaned forward in your seat. “Maybe. Not as much as he seems to think you like me.”
Jack’s pencil froze.
“How much do you talk about me, exactly? All good things, I hope.”
“All good things, yeah,” he said, a little strangled.
“Care to tell me why?” You grinned at him. You didn’t bother trying to school your face into something coy—you were all blind hope.
“There’s only good stuff to say.”
“That’s not what I’m asking, and you know it.”
He straightened, sighing. “It’s what guys do, Y/N. Talk about who they like.”
“You like me?” You leaned back, heart a mess of delight. “Jack Kelly, why, I never.”
“Yeah, well, don’t go getting a big head about it.”
“Davey said something else,” you edged.
“Yeah? Must be something terrible.”
You ignored him. “He said that you might be bringing me around the guys more.”
Jack’s cheeks were a shade of read you’d never seen on him. You sort of liked the way he wore it. “For such a smart guy, Davey never learned to keep his mouth shut.”
“Care to elaborate?”
“I was thinking of asking you to dinner,” he mumbled.
You grinned. “If you ever get around to it, I’m thinking of accepting the invitation.”
He scowled, but the edge of his lips ticced up into a smile. “Awful presumptuous of you to think I’s still asking.”
“If I asked, would you say yes?” He would ask, and you knew it. That being said, you would be willing to ask if it meant that dinner happened sooner rather than later.
Jack leaned against the desk again, a smug grin sweeping over his face. “You offering to pay, too?”
“The city would riot,” you said, smiling back.
“You’re folks would turn me away on the spot.”
“Pulitzer would fire you on principle.”
“Davey would beat me with a paper.” Jack straightened his hat, backing toward the door. “Guess I’ll bear that financial burden. Pick you up at five?”
“I’ll see you then,” you said. For the rest of the day, you would find yourself daydreaming instead of working. All of your papers bore borders of flowers and hearts, saying more about your state of mind than you would be vocalizing for months.
“I love you,” the flowering paper said. You didn’t keep that one on your wall; it made more sense to keep it in your pocket. After all, Jack Kelly was usually in your bedroom with you, so he could tell you himself.