Author's Note: New chapter! Review if you feel so led. Thanks for reading :) I hope you like it.

Chapter 5

Blair tapped her foot impatiently against the metal leg of the corner table she was sitting at. Nothing annoyed her more than lateness…that and the fact that the person she was waiting on was Dan Humphrey. There was a time when the thought of meeting Dan anywhere, much less in a public place, would have made her skin crawl. Lately, however, a strange thing had been happening. Although it took her a while to admit it, Dan was actually an asset to have at the magazine. Worse than that, she found herself seeking out his company over things non-business related. They had less than nothing in common, save for a love of movies, and his very lifestyle disgusted her. Nevertheless, she couldn't bring herself to distance herself from their unlikely friendship, which was why she was sitting in this Manhattan coffee shop…fuming.

Checking her watch again, Blair let out a loud sigh. The young couple at the table next to her glanced over but she ignored them. Any couple in matching plaid shirts clearly didn't merit her attention. She contemplated leaving, and then decided on calling Dan with a final warning.

She was rummaging through her bag for her blackberry when she noticed a familiar couple outside the window. At first she assumed it was Nate and Juliet but then the blonde he was with threw her head back in laughter and Blair recognized her…Jenny Humphrey.

Her eyes narrowed. Jenny and Nate were walking down the sidewalk, oblivious to anything going on around them. Nate had his hand on the small of Jenny's back and was whispering something to her. Jenny was laughing hysterically and shoved Nate away from her playfully. Blair watched them carry on this way until they stepped into a small café further down the block.

Blair was revolted. She was of course over Nate, had been for a while now, but even she felt he deserved better than that weasely little wannabe. What was he thinking? He couldn't really have forgotten everything she had done last year— she had made fools out of all of them.

Her thoughts were interrupted when Dan rushed in, out of breath.

"Sorry I'm late, I overslept and then I couldn't find my shoes and, well, things really just went downhill from there…" Dan trailed off, noticing the look of death on Blair's face. "C'mon Blair, it's only fifteen minutes," he said shrugging.

"Don't flatter yourself Humphrey," Blair said, rolling her eyes. "I practically forgot we were even meeting."

"Good to know," Dan said pulling out a chair.

"Anyway!" Blair said, ignoring his comment. "The real reason I'm upset is that my eyes are still burning from a repulsive PDA session I just witnessed between Nate and your little sister."

"Nate and Jenny are here?" Dan said looking around.

"They were outside," Blair said. "Although you would think they were in a hotel room from how they were acting." She took a sip of her soy latte.

"Okay, Blair," Dan said, "There is nothing going on between Nate and Jenny. Besides," he continued, raising his eyebrows, "Would it matter if they were?" He looked at her questioningly.

"Of course it would!" Blair said loudly. "Jenny ruined my life; the last thing she deserves is to be happy with another one of my exes."

"Your life isn't ruined Blair," Dan sighed. "In fact, I would say it's been going pretty well lately." He stared at her.

Blair broke his gaze, taking another sip of her latte. "If you're referring to our little movie dates, you can get over yourself Humphrey. And speaking of dates, how is Serena?"

"She broke up with me." Dan said matter-of-factly.

Blair sputtered, shocked by both his statement and its delivery. "What? Why? When did this happen?"

Dan attempted to flag down the waitress, "A few days ago. She said she didn't think we were 'meant to be,' whatever that means." He gave up, clearly not making any progress, and turned his attention back to the brunette across from him. "It's not a big deal. We've broken up before."

"Right," Blair said hesitantly. She couldn't help but fear that all the time she had been spending with Dan may have had something to do with this. "I suppose it was only a matter of time anyway. After all, she's uptown and you're Brooklyn," Blair said smirking.

"Thanks for putting it into perspective," Dan said sarcastically. Suddenly he became serious, "Really though Blair, you have to get over your issues with Jenny." He reached out and placed his hand over hers. "I'm glad we're friends Blair, I never thought I would say that but I am. But Jenny's my sister and we can't be friends if you try to make trouble for her."

Blair snatched her hand away, ruining the moment, "I'm a mature working woman now Humphrey. I've graduated from all of that high school drama." She smiled but inside her head the wheels were turning. Jenny had stolen Blair's happiness last year and now it was time to return the favor. First there was just the matter of digging up enough dirt to get the job done.

Jenny was in a foul mood. Tomorrow was her birthday and somehow Lily had talked her into throwing a party tonight to celebrate. It had started out small but now there was a guest list a mile long and the location had to be moved from the penthouse to the grand ballroom of the downtown Hyatt. It wasn't so much the details of the party that were bothering her however. It was also the fact that she hadn't heard from some of her friends back in Chicago, one in particular, who she was sure would have called her by now for her birthday. She also had to deal with the fact that Dan had convinced her to invite Blair, who he was sure had had a change of heart in recent weeks. And to top it off, she was standing in the middle of Bergdorf's, being fitted for a beautiful dress which she had no desire to wear…ever.

"C'mon Jen," Eric said sympathetically. "You look great."

He was right. The dress was stunning and it fit Jenny like it was made for her, but with all the things that had been going wrong, she felt anything but pretty.

"Fine. Can I take it off now?" Jenny asked the seamstress. She didn't want to seem ungrateful. In fact, the only reason she was going along with all of this in the first place was because it was important to Lily. Lily had been so good to her, even during all of her bad behavior last year, so she figured this was the least she could do.

Eric was waiting for her after she changed.

"Want to grab lunch?" he asked. "My treat…to celebrate."

Jenny smiled. Eric loved birthdays. Why wouldn't you when you had grown up doing them as big as all of the van der Woodsens did.

"Come on," he said, putting an arm around his best friend's shoulders. "It'll be fun. I'll be there and mom, Rufus, Dan, Nate…"

"It's okay Eric," Jenny said. "You don't have to convince me. I'm sure it will be fun." Jenny glanced down at her phone. "I've just been feeling a little out of sorts lately, that's all."

"Well, get in sorts!" Eric said enthusiastically. "You're going to need your energy up. After all, it wouldn't be an Upper East Side party without some fights, hook-ups, and shocking secrets coming to light." He jokingly clutched his chest and Jenny laughed.

"Good thing I don't have any shocking secrets."

Jenny tried going into the night with an open mind and Eric had been right, she was having fun! Although there were A LOT of people at the party, Lily had done her best to keep it casual. There was lots of delicious food (all of which Jenny could pronounce), dancing, and even a slideshow of her younger years which was embarrassing but made her feel very loved.

There had been two major highlights of the evening: first, a three-way dance off between Dan, Nate and Eric which left Jenny's stomach sore from all the laughing. Second, aside from a cordial greeting at the beginning of the night, she had successfully avoided Blair for the duration of the party.

Jenny was trying to appease a group of high society well-wishers when Nate made his way over, stealing her away, for which she was grateful.

"I haven't officially wished you a happy birthday," Nate said smiling at her. "Happy Birthday Jenny." He leaned in and kissed her gently on the cheek, lingering just a moment before pulling away.

Jenny made a face, wiping a hand down her neck. "Yuck! You are sooooo sweaty," she laughed. Her smile showed she really didn't mind. Nate smiled back.

"You're just jealous of my moves," he said, breaking into an awkward little two-step. Jenny threw her head back in laughter which only encouraged him. Nate grabbed her hand and twirled her around in front of him. She was laughing so hard that she wasn't prepared to stop and slammed clumsily into him, but Nate steadied her. Jenny took a deep breath, her cheeks flushed and a smile still on her face. Nate brushed a piece of hair out of her eyes. They began to sway to a soft song that was playing.

Jenny wrapped her arms around Nate's neck. "I'm sorry Juliet couldn't make it," she said.

Nate shrugged, lacing his fingers behind Jenny's back. "It's not a big deal; we really haven't been spending much time together lately. She's been really busy."

Jenny tilted her head to the side, "It sounds like you just need to work a little harder, that's all…if she's important to you."

Nate looked down, "Actually, I wanted to talk to you about that."

"About what?" Jenny asked.

"About, uh—" Nate was interrupted as Lily and Rufus wheeled out a giant pink birthday cake. The duo separated.

"Happy Birthday sweetie," Rufus said kissing Jenny on the top of the head and wrapping her up in a big hug.

"Thanks dad," Jenny replied.

All the guests gathered around and sang "Happy Birthday" as Jenny blew out the candles. The caterers began serving the cake but Jenny wasn't that hungry so she settled for stealing bites of Eric's piece.

"You could get your own you know, there's a whole cake over there," Eric said, feigning annoyance at the third bite Jenny stole.

"I don't want my own piece," she countered. "I just want to share yours," she said sweetly, batting her eyes as Eric tried to shield his plate from her.

Nate chuckled at the two.

"Has anyone seen Blair?" Dan asked, joining the group.

"Not since earlier," Eric said.

At just that moment, the music cut-out and Blair's voice came over the sound system. She was standing in the center of the room holding a microphone.

"Before everyone leaves for the evening, we have one more surprise for the birthday girl."

Jenny swallowed. This could not be good. Dan had already begun making his way towards Blair but she continued, "Here is a special surprise from all of your friends in Chicago!" She gestured towards the door but all anyone could see was a young man with brown hair and a shy smile making his way into the room.

It took a second for Jenny to make out what Blair was pointing to but when she saw him a huge smile spread across her face. "Matt?"

The boy smiled wider, finally seeing Jenny and rushed towards her. Jenny did the same and he swept her into his arms, twirling. Jenny laughed out loud as he spun her. He set her feet back on the ground and before anyone had a chance to ask what was going on, he kissed her.

The room was silent. Dan, Rufus and Eric had no idea what was going on. Rufus didn't like that some strange guy was kissing his daughter and Nate didn't like that Jenny was kissing him back. What was she doing? Who was this guy? Nate blamed the anger he was feeling on his protective side but deep down he knew his feelings weren't exactly brotherly.

Jenny had gotten so caught up in the moment that she forgot where she was or more importantly how many other people were there. She broke away from Matt but he was still grinning like an idiot which made her smile back—it was contagious. However, the smile didn't last when the embarrassment and confusion began to set in. Jenny pulled Matt aside and was relieved when the music came back on and people began to disperse.

"Happy Birthday," Matt said touching the side of Jenny's face. She closed her eyes momentarily, reveling in how much she had missed him before snapping back to reality.

"Matt. What are you doing here?" she asked. Chicago was too far away for this to be a chance visit.

"Your friend Blair invited me," he explained. "She thought it would be a fun surprise."

Jenny grimaced. She had already forgotten that Blair had been the one who had announced Matt's arrival, who had set this all in motion. But how had she found out about him? Jenny hadn't even told Dan about Matt. And what was her angle? It wasn't like bringing Jenny's super cute friend/boyfriend/acquaintance-of-an-undefined-manner to town was really the most devastating thing Blair could cook up.

Matt noticed the change in her demeanor. "It is okay that I'm here right? I mean your friend said—"

"She's not exactly my friend…" Jenny interrupted. She really did not want to go into her history with Blair right now considering she hadn't told Matt about anything that happened last year. In fact, she had pretty much only told him the bare essentials of her life in New York. Suddenly, she was seized with panic. What had Blair told him? Was that what this was all about? Airing her dirty laundry in front of the most important person in her "new life."

"Jen?" Matt asked. Now he was the one who was confused. "What's going on?"

Before Jenny had time to answer, or think of an answer, Rufus walked over. Her was followed closely by Dan, Nate, Eric and Lily.

"Jenny, who is this?" Rufus asked. Eric had that guard dog look on his face again and Nate…well Nate had a look on his face that Jenny couldn't quite figure out but she didn't have time to worry about that right now.

"Dad, this is my, um…this is Matt," Jenny said stumbling over her words. She suddenly felt like she was a six-year-old about to be reprimanded by her father. She was reassured by Matt stepping forward, placing one hand on the small of her back and extending the other towards Rufus.

"It's nice to meet you Mr. Humphrey," he said, shaking Rufus's hand. "I've heard a lot about you."

"That's ironic, we've heard nothing about you," Dan quipped.

Jenny shot him a look, "Matt, this is my brother Dan. I've told you about how he can be." Dan made an offended face but Jenny continued down the line. "And this is my best friend, or well step-brother Eric. And my step-mother Lily. And this is Nate." Jenny wasn't sure why she didn't give him a label like the others. "Everyone, this is Matt. We go to school together in Chicago."

"It's a pleasure to meet you Matt," Lily said, always the picture of class. "Chicago is quite a ways away; I hope your trip went well."

"Very well," Matt said, looking down at Jenny. "Time flew by." Jenny blushed. Nate shifted uncomfortably.

"What brings you to New York so unannounced?" Rufus asked, clearly still wary of Matt.

"I wanted to surprise Jenny for her birthday," Matt explained.

"So," Eric finally spoke up, and gave a voice to what everyone was thinking, "Are you two like, dating?" He was annoyed that this information had been kept from him.

"Okay," Jenny broke in. "That's enough with the questions for now. It's late, I'm sure Matt is tired," she said turning to him. "Maybe we should call it a night and we can all talk more tomorrow." She desperately wanted time to debrief him before he faced the firing squad.

"Just a minute," Rufus said sternly. "He will not be staying at the loft, I don't think so."

Jenny rolled her eyes but before she could make a bratty comment Matt spoke up, "Actually, I have a friend who lives in the Soho area so I'm going to stay with him while I'm in town. I have a rental car, can I give you a ride home first?" he asked Jenny.

"Yes," Jenny smiled. "I'm beat anyway," she said turning to Lily and Rufus. "Thank you for the party. It was great." She hugged them both. "I'll be fine," she said pulling away from Rufus.

"Call me as soon as you're home," Rufus said. "And Matt, we'll see you tomorrow morning for breakfast." This was really more of a demand than a question.

"Sounds great," Matt said. He was always an optimist, that or just really dense. Either way, it was something that had first attracted Jenny to him. "It was nice meeting all of you," he said.

"Dan, do you want to come with?" Jenny asked her brother.

"No. I, uh, need to have a conversation with Blair," he said, rubbing the back of his neck. Jenny gave her brother a sympathetic smile. She had tried to warn him but a part of her felt bad for Dan. He really had believed the best in Blair.

"Okay. Love you all," Jenny said as Matt took her hand and led her towards the door. She mouthed "I'll call you later" to Eric as he shot her an incredulous look. They were about halfway to the door when Jenny stopped.

"Shoot!" She said. "I forgot something. Meet you outside?" she asked.

"Sure," Matt said, kissing her on the cheek. "I'll pull the car around."

Jenny smiled as he left. She didn't have the heart to explain that everyone around here used valet. She turned and scanned the room, spotting Nate alone at a table at the other end of the room.

"Hey," Jenny said, walking up and making him jump. He had clearly been lost in thought.

"Hey," Nate said. "I thought you left."

"I am…we are," she said glancing in the direction Matt had gone. "But I didn't want to leave without talking to you first."

Nate raised his eyebrows. "Talking to me?" he asked.

"Yeah," Jenny explained. "Earlier you said you needed to talk to me about something."

"Oh yeah," Nate said, understanding what she was referencing even though she really didn't. "I, um, just wanted to say, uh…happy birthday."

Jenny smiled, "You already said that."

"Right," Nate said smiling back. "Well I really mean it." He paused before continuing, "You're really important to me Jenny."

Jenny lost her smile. Suddenly the moment felt much more serious. "You're important to me too Nate," she said. She stepped towards him, enveloping him in a hug. Nate lowered his face to the crook of her neck, breathing in her scent. All too quickly, Jenny pulled away. She smiled at Nate. "I'll talk to you tomorrow, okay?"

"Yeah, talk to you then," Nate replied, forcing a smile which he held until Jenny had reached the door and disappeared outside. Then he slumped back down in his chair.

"I hate Upper East Side parties."