Chapter Six: behind everything simple is a huge tail of complicated

Jack had been looking for Crutchie or Race or one of the older boys (even, perhaps, Davey, though he didn't know how well he'd be able to help Jack with this particular predicament). He wasn't expecting to run into Romeo – sitting on the rooftop, no less. "Hey, Ro," he said warily, wondering if something had happened for him to be up here. Usually Jack and Crutchie were the only ones who came to the roof; occasionally Race as well. That was about it. "What's goin' on?"

"Oh," Romeo jumped slightly, clearly not having anticipated Jack's arrival. "Hey, Jack." He scrambled to his feet. "Sorry, I- I was just-"

"It's fine, calm down," the older boy said with a chuckle. There wasn't some sort of rule that kept newsies from visiting the roof, it was just that no one ever did. Maybe it was out of reverence. Maybe it was out of a fear of heights. "Just wasn't expectin' it, is all. Though, uh- it's pretty cold out here."

Romeo shrugged with an awkward grin. "Guess I just needed the air." He moved to leave, and an idea struck Jack. Yes, he had been looking for Race or Crutchie, but if the self-proclaimed Romance Expert was right in front of him, then...

"Say, while you's up here...I got a bit of a situation I was wonderin' if you could help me out with."

"Oh yeah?" Romeo turned back around, intrigued. "Yeah, what's goin' on?"

"Well, ya know Katherine. Obviously. And I, uh, I wanna impress her with somethin' big, some grand romantic gesture to really show her I cares – but I been thinkin' for a month, and I got nothin'."

Romeo suddenly grinned, walking over to Jack and putting his arm around him (which he had to reach up to do). "Well, well, Mr. Kelly, you've come to the right person."

Jack chuckled again. He'd intended for this conversation to be something more insightful than perhaps the playful and childish Romeo could bring, but why not? He wasn't exactly on a time limit, and he didn't need to make this conversation deeper than it had to be. He didn't have to mention how he saw Katherine almost every day, and how he'd spend time with her often and in the moment think maybe that – the just being there, with her – was enough, but then he'd leave or she'd leave and he'd wonder again how long it might be until they parted ways and did not return to each other. He didn't have to bring up how he'd never had someone that wasn't a newsie stay with him so long before, and a part of him (a larger part than he'd like to admit) was still convinced Katherine was too good to be true. And he certainly wouldn't say how despite them coming up on six months of being together or at least liking each other there were just some things he was scared to talk about with her. How he opened up as best as he could, but for so long being vulnerable with almost anyone only got him in trouble. How for the past month or maybe longer, that feeling that he wasn't doing enough to justify how well she treated him was in the back of his mind, waiting to resurface when he wasn't actively distracted. How he was certain he loved her, but not certain she felt the same.

He wouldn't say any of those things to Romeo because Romeo didn't need to know them.

And who knew? Maybe some lightheartedness was just what Jack needed. Maybe he was thinking too much about this and that's where his problem was.

"So how grand are ya thinkin' here?" Romeo said, starting to pace and snapping Jack from his introspection. "And how romantic? 'Cause y'know, you could always go with the classic 'flowers and candy' or 'dinner and a movin' picture."

Jack stared at him bemusedly, wondering just where Romeo had gotten the idea that he could afford any of that. Most of his money went to the newsies, helping cover their rent and food and even putting away some extra just in case – the strike had drained them financially, and though there was almost no chance of them striking again, who was to say there wouldn't be some other emergency? And he did make more money now, but enough to just casually spend on a decent movie and dinner that wasn't a sandwich at Jacobi's? Not likely.

Romeo seemed to catch onto this, and momentarily stopped his pacing. "...Or, seein' as there might be some...monetary restrictions on the classics – why not play to your strengths? You's a great artist, Jack. You can paint her one of them backdrops you's always makin' for Medda, or draw her a portrait!"

"Ya think I ain't thought of those already?" He wasn't actually upset at all.

"Maybe you could write her a poem? See a show in the park together? Go look at the stars?" Romeo paused. "Okay, so those things ain't exactly grand... but grand ain't always an option, either. Not for guys like us. And- I know you's off makin' money with the big leagues now-" here he did a mock bow, as if Jack making a few more cents an hour had turned him into royalty, "- but if Katherine really loves ya, she ain't gonna expect all the fancy stuff. I think maybe… just the little things is enough."

Though it almost felt odd, coming from Romeo, it sounded like exactly what Katherine would say. And it was true.

Maybe he just needed to hear it from someone that wasn't his easily ignored common sense.

"'Sides," Romeo added with a snort, "she already looks at you like ya hung the moon. Don't think there is much more you could do to impress her." There was something like wistfulness in his voice, and he sat down again.

"You'se probably right, kid," Jack said, sitting beside him with a sigh. "It just feels like-" he began to cut himself off, remembering his internal vow not to share too much, but Romeo beat him to it.

"Like ya can't do enough," he said. "And like if you're just yourself for too long she'll get bored or annoyed. So ya gotta keep doin' more so she don't go find someone else, except ya got no clue what to do so ya just hope you really is enough to keep her there."

Jack, once again surprised to hear this coming from Romeo, turned to look at the younger boy, but he was staring in the distance. Jack wondered if there was anyone specifically Romeo was referring to. He looked uncharacteristically pensive and serious, and it almost took Jack aback.

"Sorry," Romeo began, breaking the silence. "Didn't mean to get all deep and personal. Might not even be what you was feelin'. Sorry, I just-" He moved to leave again.

"Hey," Jack said. Romeo stopped. "You okay?"

"Huh?" He looked, briefly, as though he hadn't been expecting the question, but the expression that had flickered across his face was gone almost as quickly as it had come. "Oh. Yeah. Fine!" He gave Jack a half-hearted smile. He opened his mouth, looking like he'd say something more, but closed it and left the rooftop without a word.

Jack was left alone to wonder just who or what had made his little brother so melancholically ruminative...and why he felt he had to hide it.

A/N: Another short chapter, but a very important one that's referenced later! I've always wanted to explore Romeo's character - and the notion that he's not quite so sunny all the time - so I hope this is the start of me doing that well! Sorry about the impromptu several-month-long break, but hopefully I can get back into writing easily enough! I hope you guys are still enjoying the story, and I'd love a review hearing your opinions!