The pair laughed and talked until they arrived in front of Medda's theatre. As they waited in line for the doors to open, Katherine continually glanced over at Jess, trying to find the right way to form the question she needed to ask her friend. Jess sighed as Katherine glanced over at her for the fifth time. "Alright, spill. What is it? You've been dying to ask me something the entire way over here," Jess laughed. Katherine giggled along with Jess. "Sorry, am I that obvious?" Jess nodded as the line began to move inside the theatre. "Yes. Incredibly obvious." The two found their seats in the top balcony and sat down. Katherine sighed. "I thought I was doing an okay job at it, too." Jess shook her head. "So anyway. Spill it!" Katherine laughed. "Well, I just wanted to know how you like being a newsboy." Jess turned to her confused. "I love it. It's so much better than being with my godfather, but you already know all of this..." Katherine nodded her head and ignored the last part. "Good, good. And I notice that you have a selling partner. How's that going?" Jess glanced at her friend curiously. "Crutchie? He's nice. He does his job well." Katherine nodded. "That's nice. Anything else?" Jess crossed her arms and looked questioningly at Katherine. "Okay. I'm putting an end to this. What're you trying to do?" Katherine threw her hands in the air, exasperated. "Ugh! Do you like Crutchie or not?" she exclaimed. Jess laughed. "Well, yeah! I mean I live with him and Jack! I guess I have to like them, don't I? They're like brothers to me." Katherine groaned. "You know what I mean!" Jess blinked. "You mean romantically? Honestly, I've never really though about it before." Katherine squinted at Jess as she leaned towards her. "Are you sure?" "Positive! I mean, he is really nice and adorable and I love to spend time with him..." she trailed off before slapping her hand to cover her mouth and look at Katherine in surprise. Katherine smiled, satisfied, as she leaned back into her seat. "Sounds like you have thought about it, even if you didn't know it." The lights of the theatre suddenly dimmed and the overture to Medda's show began, but Jess continued to think about what had just happened. Did she really like Crutchie? Did he even like her? What if it didn't work out? Medda walked onstage and Jess let all her worries leave her mind for the time being, but the last thought in her mind continued to ring: should she tell Crutchie of her feelings?
Crutchie climbed up onto the roof with Jack following close behind carrying a bag of sandwiches. The sun was just beginning to set and the sun reflected off of the buildings. Jack passed Crutchie his sandwich and the two sat chewing quietly, watching the sunset. Jack became lost in though as he tried to come up with a way to get his best friend to come clean with his feelings for Jess. He didn't want to let Katherine down and he knew that Crutchie liked Jess a lot. Jack as startled out of his thoughts when Crutchie said, "Hey, Jack? Youse been awfully quiet for the last half hour. Watch thinkin' about?" Jack stumbled for words. "Well...ya see...ah..." Jack blushed red as he realized he didn't know what to say. Crutchie laughed. "It's okay! Youse can tell me." Jack rubbed the back of his neck. "Well, it's kinda complicated." Crutchie looked at him confused. "Then youse can simplify it," he laughed. "Okay, Crutchie. Whaddaya think about Jess?" Crutchie looked taken aback. "Why?! Do youse not want her to stay with us anymore?" he asked in a panic. Jack shook his head quickly. "No, no, no. That's not it at all! Ise just wanted your opinion of her." Crutchie looked relieved. "Oh. Well, she's super nice and caring. And she's pretty good at playing poker. Wipes everyone else out." Jack sighed. "But, Crutch, do youse like her?" Crutchie snorted. "Well of course! Don't youse?" Jack threw up his hands and laughed. "Youse missin' the point here!" Crutchie crossed his arms over his chest and thought. "No I ain't! Youse asked me if I liked her and Ise said..." Realization dawned across his face as he understood Jack's question. The crippled boy began to blush as he said, "Oh..." Jack laughed at the younger boy's expression. "Yeah." Crutchie though for a minute. "Well, I do really like her, but Ise been afraid to say anything to her." Jack smiled knowingly. "Youse should tell her, Crutchie." Crutchie looked at his friend. "But what happens if she doesn't feel the same way?" Jack grinned. "Ise really doubt that."
The two friends sat until a voice broke the comfortable silence. "Hello? Anybody home?" "We's up here, Katherine!" Jack called down. Steps were heard on the ladder as Katherine's head appeared. "Hi," Katherine said to her boyfriend as she gave him a hug. Crutchie got to his feet. "Where's Jess?" he asked. "Here I am!" a voice called out. Crutchie turned back to the ladder as a girl he didn't recognize climbed up onto the roof. Jack let out a low whistle. "Wow, Ace. Youse did a great job! You look great, Jess," Jack said. Jess blushed as Crutchie hobbled over to her. "Jess, youse look amazing." Jess smiled. "Thanks, Crutchie." Katherine glanced at Jack. "Well, Jack, you promised you'd walk me home." Jack nodded and followed Katherine towards the ladder. "Catch youse two later," Jack said, and then they were gone. Silence enveloped the two. Jess picked up the bag Katherine had left and put her newsboy clothes near her mat, along with the extra skirts and blouses Katherine had given her. She glanced over her shoulder at Crutchie. "Would ya mind turning around so I can change?" she asked quietly. Crutchie nodded, and turned to look out over the city. After a few minutes, he head Jess say, "Okay, you can turn back now." He turned to find her out of her nice dress and into a pair of pants and an old t-shirt of Jack's, but she still looked as beautiful as she had when she had gotten back from Medda's. Jess joined Crutchie by the edge of the building and silence once again covered the two as they stared out at the city and the stars. Jess broke the silence first. "If you look in that direction, you'll see Ursa Major," she said, pointing to the sky. Crutchie followed her direction and was surprised to see a bear in the sky. "And over there is Cassiopeia, and over there is Orion, and farther is Draco," she continued. Crutchie looked over at her. "How do ya knows this much about constellations?" Jess smiled as she continued to search the sky. "My father loved astronomy. He used to show me all the constellations when I was younger." They became lost in their own thoughts. Suddenly, a shooting star crossed the sky, causing Crutchie to gasp. "Pretty, isn't it?" Jess asked. "My dad used to say you could wish on those." Crutchie looked into the section of the sky where the star had appeared and made a wish. He glanced towards Jess and took a deep breath. "I have to tell you something," both Jess and Crutchie blurted out at the same time. The two turned and stared at each other in surprise before bursting into laughter. "You first," Jess told Crutchie. He smiled shyly and looked down. "Well, Ise was talking with Jack today and he actually talked to me about you. He wondered how I felt about youse and I told him the truth." Jess glanced over to him. "And that was..?" Crutchie took a deep breath. "That Ise really like you, Jess. I don't know if youse feel the same way, but Jack said Ise should tell you and how Ise felt and..." Crutchie was cut off by a hand touching his own. He looked up at Jess' face and was surprised to see her smiling. "Crutchie, I feel the same way." He let out a sigh of relief and laughed. She laughed with him and watched the sky, still holding hands. "You know..." Jess began. Crutchie turned to face her. "katherine asked me similar questions about you..." Jess began before looking at Crutchie quizzically. Crutchie laughed. "Of course. It was probably all part of her plan to get us together." Jess giggled. "I guess we should be glad she did, then." The two turned back to the stars as they allowed a comfortable silence to envelope them once again.