Author's Note: Hey guys, sorry it has taken me FOREVER to add a new chapter. Hopefully people are still reading. Enjoy!

Chapter 6

Jenny strummed her fingers on the countertop and checked the clock for the fifth time in the last four minutes. She was alone in the loft waiting for Matt to pick her up so they could drive to the penthouse for brunch. Dan had left a little while before, fed up with Jenny's constant pacing, although he claimed it was to make sure everyone was on their best behavior before the couple arrived.

Jenny couldn't believe how nervous she was. There was something unsettling about her life in Chicago crashing so abruptly into her life in New York. Not that she was worried about her family accepting Matt himself. He was one of the most charismatic guys she had ever met. He had this ability to put people at ease which was what drew her to him in the first place…not that she had made it easy.

The first time Jenny met Matt it had been her first day at her new school in Chicago. She arrived a few days before the semester began and was trying to get situated in the dormitory-style room she had been assigned to stay in with a peppy brunette named Amber. Amber was in her second year at the school and had plenty of friends so Jenny was left alone to unpack on her first Friday night in the new city.

She was simultaneously blaring the Ramones, feeling sorry for herself and her pathetic life, and folding sweaters when someone knocked on the door. Before Jenny had a chance to answer, the door swung open, revealing a tall, brown-haired boy wearing a bright green 4-H t-shirt.

"Hey, did you order a pizza? 'Cause there's a guy downstairs demanding $12.50 for a deep-dish pepperoni and there are only a couple of us here, and I've pretty much checked with everyone else so…"

Jenny stared at him incredulously. "Have you ever heard of knocking?" she demanded. She felt all of the tension in her body that had built up over the last few days shooting out of her eyes and directly at the intruder.

Matt gazed at her for a few seconds and then broke out into a huge grin, which only made Jenny angrier.

"Sorry," he said. "Usually I'm worried about someone being naked or having sex when I knock and I've never heard of anyone being in the middle of either of those with music playing that loudly." He kept smiling, clearly amused.

Jenny didn't know which infuriated her more: that this guy she didn't even know had barged into her room, or that he clearly wasn't put-off by her angry look and dark makeup like everyone else she had encountered thus far.

"The volume of my music doesn't give you the right to barge into my room," Jenny bit out. She was quickly becoming unnerved by the way he was staring at her with the same smile on his face. "Besides," she added, "maybe I like having sex to loud music." She delivered this line completely stone-faced. That should do it, she thought, proud of herself.

"Good to know," Matt replied nonchalantly. "So do you want a slice?"

"What?" Jenny asked, confused. He had deflected her sex comment like it was nothing and now she had no idea what he was talking about.

"Do you want a slice?" Matt repeated. "…of pizza. I'm not completely convinced you didn't just order it as a way of getting me to come up here and introduce myself but I'll be the bigger man and foot the bill…just this once."

Jenny could have sworn he actually winked at her as he said this. Was he joking? "That's ridiculous," Jenny said. "I would have had no way of knowing you would even come up here."

"You're right," Matt agreed. "I guess it is a little far-fetched. You're probably more of a salad girl anyway." He turned to leave her room. "Oh and it's Matt by the way," he added.

Jenny looked at him. On one hand, she was seriously considering throwing something at his head, but on the other, she was slightly impressed that a boy with a Midwestern accent would be so unbothered by her bad attitude and ripped fishnets.

"Jenny," she finally said.

"I guess I'll see you around Jenny," Matt said.

"Sure," Jenny replied. "And Matt?" He turned to face her. "The next time you want to say hi, you don't have to make up some lame pizza story to do it."

That made Matt smile, really smile.

Jenny's trip down memory lane was interrupted by a knock at the door. She practically leapt up to answer it. Matt was standing on the other side, giving her that same happy grin he had the first time she met him.

"Am I late?" he asked. "You look kinda annoyed."

Jenny smiled shyly. "Not annoyed," she said. "Just a little nervous."

Matt threw his arm around her shoulders and led her into the hall. "Don't be nervous, I've been going over some of my best jokes. They're going to LOVE me."

Jenny groaned as Matt laced his fingers through hers. This was going to be a long day.

Jenny was relieved that Matt had been kidding about the whole joke thing. Not that it mattered, both Serena and Lily found every word that came out of his mouth to be absolutely hilarious. Even the men seemed to be warming up to him, with the exception of Eric who kept the same hesitant look on his face throughout most of the meal.

Aside from the constant questions from her father, things were going pretty smoothly. Matt explained how he had moved to Chicago from Ohio when his father got a job there. The transition had been rough but it had helped him realize that he had a passion for graphic design, which had led him to the school and consequently, Jenny. Then of course they all wanted to hear how the couple had met, although Jenny gave the paired down version, altogether eliminating the sex comment. They were all stuffed and finishing up with coffee when the topic of conversation changed to their plans for next year.

"So Matt, you and Jenny have both earned enough credits to receive your high school diplomas. What are you going to do next?" Lily asked politely.

"I actually got accepted to SAIC and they have openings this spring. We're really excited," he replied.

"We?" Eric asked suspiciously.

Matt glanced at Jenny who was doing her best examination of the inside of her coffee cup. "Yeah…" he said slowly. "Jenny was accepted too. You told them, right Jen?"

Jenny looked up. "I meant to, I just hadn't yet." She looked at her dad. "I got accepted to the School of the Art Institute of Chicago." She smiled hesitantly. "Surprise!"

"That's great sweetie, congratulations." Rufus smiled but it didn't quite reach his eyes.

"Yeah Jen, that's a great school. We're proud of you." Dan added, squeezing her shoulder from where he was sitting next to her. "But I thought…I mean, I guess we kind of all assumed you would be coming back to New York once you received your diploma."

Jenny didn't know what to say. When she first came back to the city, she had been dreading it. She felt like she had pretty much made up her mind that Chicago was where she wanted to be. But now, being back with her friends and family, she realized that this fit too. She didn't know how to respond in a way that would satisfy everyone she cared about.

"I don't know. SAIC is a really great school and I haven't heard back from Parsons. Spring isn't for a little while anyway so…"

"You applied to Parsons?" Matt asked. This was new information to him as the couple had only ever talked about starting SAIC together.

"Um, yeah." Jenny replied. "I was going to tell you, I just…"

"Why wouldn't she apply there? Parsons is the best design school in the country." Eric interrupted. He could not believe Jenny was actually considering staying in Chicago. Sure they had argued about it over the last few weeks but in the back of his mind he had just thought she was being stubborn and would eventually give in.

"Eric…" Serena interjected. "I'm sure it's not an easy decision. Calm down."

"I am calm," Eric replied defensively. "It just makes sense that Jenny would want to be where all the most important things in her life are."

"And all the worst." Matt added.

The table fell silent. Matt didn't know all of the details of why Jenny left New York but he knew that it was bad enough that she refused to tell him about it when they shared everything else in their lives.

Jenny's head was spinning. This conversation had spiraled out of control. If she was confused about what she was going to do before, she definitely had no clue about what to do now.

"I need some air," she said, excusing herself from the table.

"Jenny, wait." Matt said, standing. "I'm sorry. I shouldn't have—" But Jenny was already out the door.

"I'll check on her." Dan said, following his sister. Matt sat back down, a defeated look on his face.

Jenny sucked in a big gulp of air as her feet touched the sidewalk. Although it was much louder on the busy street, she instantly felt calmer away from the questioning stares and awkward silence of the table. She heard her brother clear his throat behind her. She turned to look at him, expecting a sarcastic remark to break the tension but instead Dan just held out his arms and she walked straight into them. Immediately she started to cry, not a lot, just little sniffles. Dan tightened his grip on her and smoothed her hair. After a few minutes she calmed down, stepping back and wiping the tears off of her face.

"How's my makeup?" she asked.

"A big improvement from last year," Dan replied jokingly. Jenny punched him in the arm. "Ow!" he said, feigning pain. "See if I ever run after you again."

Jenny smiled. Dan always knew how to distract her from her problems.

"What should I do Dan?" She asked. If anyone knew how difficult coming back to New York had been for Jenny it was her big brother. Afterall, he had been the one constantly warning her about the evils of the Upper East Side. If only she had listened.

"I don't know Jen," he said, draping one arm around her shoulders. "But whatever you decide, you know we'll all support you."

"Even Eric?" she asked.

"Maybe after he gives you the silent treatment for the first few months." Dan smiled sympathetically.

"Hey." Matt said softly from behind them as he stepped out of the building.

"Hey." Jenny said, smiling slightly.

"I'll leave you to it." Dan said, kissing Jenny on the forehead and walking back inside.

The two stood in silence for a few minutes. "Look Jenny, I'm really sorry," Matt began. "I shouldn't have said that, about the bad stuff. I'm just a little confused okay? I thought I was coming here to surprise you and we would get to spend some time together and then I find out the girl who invited me has some kind of vendetta against you and now you're not even sure if you're going to come back to Chicago? It's all just a little much."

"I know," Jenny said. She felt tears stinging her eyes again but blinked them away.

Matt stepped forward and lifted her chin. "I'll be honest. The only thing that has gotten me through the past few weeks and you being away is knowing that you'd be coming back. When that became uncertain, I guess I just got defensive."

Jenny met his eyes. "Matt, I know there is a lot that I need to tell you and it isn't fair that you have to be in this situation and dealing with all of my baggage—" her voice cracked.

"Jenny," Matt said, wiping away a stray tear. "I've never asked you to tell me because it doesn't matter what happened before we met. The girl I fell for is the girl I met in Chicago. Whatever happened to get you to that point is just water under the bridge." Jenny smiled, Matt had always been this way with her but it still always felt surprising.

"I want you to do whatever makes you happy. And while I selfishly want you in Chicago with me, I also honestly think that's where you're happiest. I know you were in a dark place at the beginning of the year and you're so different now, and I think that's because you love Chicago."

"And because of you," Jenny added.

Matt smiled sheepishly. "We'll make it work okay? Whatever you decide."

"Okay," Jenny agreed. She didn't have any extra clarity on the situation but she was relieved that she hadn't ruined the one good thing that came out of her running away to Chicago.

"We should go back up so I can say goodbye to your family." Matt said.

"Yeah," Jenny said. "Let's go."

Jenny didn't get back to the loft until 10:30 that night. She had spent the rest of the day after brunch showing Matt around the city and doing her best not to think about the future. He had decided to head back to Chicago in the morning. He didn't come right out and say it but Jenny knew he was cutting the trip short because he didn't want to add any stress to her life by being there. She had tried to convince him to stay for a couple more days but he very sweetly (as usual) declined. He told her he would see her in three weeks, when break was over. Whether or not that would be in Chicago, Jenny wasn't quite sure.

She walked into the kitchen and threw her keys on the counter. There was a note from Dan explaining that he went out for a little bit and would be back later. Normally, she would have just assumed that he was with Blair but he was pretty upset with her since they had spoken at the party and Blair admitted that she invited Matt to New York to humiliate Jenny by telling him all about last year. Of course this didn't happen seeing as Dan had completely ended their friendship that night after she told him and surprisingly, Blair had backed off.

Jenny suddenly felt physically and emotionally exhausted. She changed into a pair of boxer shorts and one of her dad's old Lincoln Hawk t-shirts and plopped down on the couch. She felt like she should wait up for Dan but based on how heavy her eyelids felt, she wasn't sure that would happen. She was starting to drift off when there was a knock on the door.

"Nooooo." Jenny whined. She got up with a sigh, not certain she could take any more surprises. She was relieved when Nate was on the other side of the door.

"Hey," she breathed out. She was really glad to see him after the day she had had.

"Hey," Nate replied. "Are you okay? You look like you don't feel well."

"Thanks," Jenny laughed, stepping aside so he could come in. "Is giving me an ego boost the only reason you're here?" she asked sarcastically.

"I didn't mean it like that." Nate said. "You know I always think you look great." Jenny blushed, caught off-guard by his comment. He quickly changed the subject. "So, uh, how was brunch?"

"Good," Jenny said. "But also a disaster."

"Yeah," Nate said. "I talked to Dan earlier, he filled me in."

"Right," Jenny said. She wondered how Nate had reacted to the possibility of her returning to Chicago, not that he would care.

"Well I'm sick of talking about it. Tell me something to take my mind off of it." She said, returning to her seat on the couch. Nate followed suit, sitting beside her.

"I broke up with Juliet," he said abruptly.

Jenny was shocked by his sudden omission. "Oh. I'm sorry," she said. "I guess a lot has happened since last night for both of us."

"Yeah," Nate smiled. "Especially in our love lives." He was attempting to lighten the mood but the truth was he was surprised and strangely disappointed by the fact that there was a new man in Jenny's life. Not that he had expected her to abstain from dating while in Chicago, but in all the time he had known her, she had really only had one constant love interest…him.

Silence hung between them.

"You should hang out with Matt sometime," Jenny said quietly. "I think you would really like him."

"I bet." Nate said. "Maybe we can do something while he's in town." Jenny was quiet. "Or not," he continued, interpreting her silence negatively. "I mean we don't have to. I'm sure you want to spend as much time with him as possible."

"It's not that," Jenny assured him. "He's actually leaving for Chicago tomorrow morning."

"Oh," Nate said. "He misses deep dish pizza that much, huh?"

Jenny chuckled, "Yeah, something like that. What about Juliet? Why did you guys break up?"

"We just weren't connecting," Nate said. He paused. "Actually that's a lie." Jenny looked at him questioningly. "I broke up with her because I think I have feelings for someone else and it wasn't fair to lead her on." Jenny just stared at him. Nate swallowed, trying to muster all of his courage. "You know how, sometimes, there are people in our lives who we always seem to come back to?" Jenny nodded. "But after a while it seems like things haven't worked out so many times that it would be stupid to take another chance on it?"

"Yeah," Jenny said, smiling slightly. "I do."

"Really?" Nate asked, hopeful.

"Of course." Jenny replied. "Look Nate" she put her hand on his arm, "I think you should tell Serena how you feel."

Nate's face fell.

"I know you two have a long history and she really hurt you last summer but if being with her is what could make you happy then you have to at least try."

"Jenny—"

"That's how it was with me and Matt."

Nate stopped what he was saying and Jenny continued. "Last year I was a mess. With Damien, then throwing myself at you…and Chuck." Jenny's cheeks flushed at the memory. "I had completely sworn off men. But then I met Matt, and while it took a lot of convincing on his part, I opened up to him and took a chance on love again, and it's been great…he's been great. I feel good about myself again, and it's been a while since I could say that."

Nate was quiet. Jenny had completely misinterpreted what he was trying to say. Her eyes had lit up when she was talking about Matt in a way he had only ever seen when she was with him. He should have been happy for her as a friend, that she had finally moved on. But he only felt utterly dejected.

"You're right Jenny," Nate lied. "Maybe I will tell her. Listen I've got to go okay?" he said standing up.

"Sure," Jenny said, walking him to the door. The stopped in front of it and Jenny got up on her tip-toes to kiss his cheek. "Any girl would be lucky to have you," she said. "Remember that, okay?"

"Okay," Nate said "Goodnight Jenny."

"Goodnight," she said, closing the door behind him.

Nate stood outside the loft staring at the closed door for a few seconds. Then he shoved his hands in his pockets, preparing for the cold walk home.