Disclaimer: Newsies belongs to Disney.
Jack didn't believe in love at first sight. He wasn't a sap. That kind of stuff was for the same suckers who believed in happy endings. But from the very second Jack laid his eyes on Miss Katherine Plumber, he knew he was already falling hard. Jack could've sworn that she was an angel who had descended from the heavens to save them all.
So he flirted a little. He wasn't at all surprised when she rebuffed him, no. Jack knew from a young age that girls like her wouldn't ever fall for guys like him. However, he was quite shocked to find that she had kept his drawing, or even bothered to look at it. He, of course, acted like it was no big deal, but inside, he felt warm and fuzzy.
Often times, Jack would absentmindedly start sketching her, or staring off into the distance. His behavior didn't go unnoticed by the boys, of course. Every time it happened, they'd start chuckling and nudging each other, nudging Jack, smug grins plastered onto their faces. They all knew their friend was thinking about a certain female reporter. When confronted by Crutchie, Jack politely denied it, and quickly changed the subject. After all, he was Jack Kelly, leader of the Newsboy Strike; he had more important things to think about than love.
When he actually had the opportunity to sleep, Jack found himself dreaming not of colorful sunsets out West, but of the face of none other than Katherine. She was beautiful, definitely. And witty. She could stand up for herself, and man, was the woman brave. There was a lot to admire.
Maybe, Jack thought, when the strike settles down-no, no, that would never work. He could still admire from afar, though, right?
Katherine was in denial. Lately, completely against her will, her thoughts were constantly plagued by the charismatic strike leader, Jack Kelly. She hated herself for it. To think so much about him-it wasn't right. Of course, it's not like she liked him. No way. She so hated that attractive cocky smirk always on his face-what a face he had, by the way-and the way he thought that she was just some airheaded girl who would fall head-over-heels for him with just a few flattering words! How dare him! Still, Katherine sensed there was so much more to Jack. The way he treated his fellow Newsies like family, the passion in his voice when encouraging them, and the drawing…Yes, there was definitely something about that boy.
As soon as she heard that Crutchie had been captured, Katherine was very concerned. Well, firstly, for Crutchie, but next, for the other Newsies. Especially one of them. What had become of Jack? When she had showed them her article in the deli, she was glad that the Newsies were ecstatic. But, she was disappointed that Jack couldn't see it right then, and was worried because no one had seen him since the strike. She'd find him later.
By the end of their encounter on the rooftop, Jack and Katherine had broken down the barrier.
First, the kiss. Both of them could still feel the tingling sensation.
Katherine was nervous. Who knew how Jack actually felt about her, about this?
Jack was unconvinced. How could such a perfect girl like a poor boy such as him?
Unsurely, they both let their feelings loose. They realized they both had something to believe in because they believed in each other. Even if what they had was only for a day, and Jack left tomorrow, the things they shared would be stay with them forever.
Social class, or even Katherine's father, Pulitzer himself, couldn't stop their love for each other. No matter where he went, she would be there, right by his side, no matter where he chose to go.
The strike was now over, and the Newsies got a square deal. And Jack realized that happy endings could exist. Dreams could come true. But Jack's dream wasn't in Santa Fe, but right here, at home, with his family and friends, and a girl who loved him.
"I love you."
"For sure?"
"For sure."