Author's note: This is how I envisioned Season 4, and Jenny Humphrey's return, playing out. I'm not sure how long this story will be yet, I'm going to wait and see what people think of it.


Chapter 1

Jenny took a deep breath, filling her lungs with crisp autumn air as she stepped off the train and onto the bustling platform. While there was a big part of her that immediately felt at home being back in the city, a bigger part had to remind her to breathe in order to keep her anxiety at bay. It had been almost a year since she left the Upper East Side, her old life, and the giant mess it had become. She had spent the last several months in Chicago at an innovative design school that allowed her to finish high school while prepping for a career in design. She loved Chicago, every part of it. It was so different there. It took a while, but for the first time in a long time she felt like she belonged somewhere. She had real friends and she wasn't suspicious of their motives or afraid they would turn on her for wearing the wrong shoes. She wished she was back there now. But instead, she was back in New York with a long fall break ahead of her.


She recognized Dan's voice. Glancing down the terminal, she saw her brother and father heading towards her, huge smiles on their faces. She smiled back and made her way towards them. They were the one thing she had missed about home. Well, and Eric of course.

"Oh sweetheart, I've missed you," Rufus said enveloping her in a big hug. He stepped back, not letting go of her shoulders. "Let me look at you. I barely even recognize you."

It was true. Jenny did look a lot different. The change had been gradual, but as things in her life had become lighter, more carefree, so had her look. Her hair was shorter, just past her shoulders, and a darker more natural looking blonde. Her face had barely any makeup, save for some concealer and mascara. Her outfit consisted of a long loose gray sweater over dark skinny jeans and navy Keds. She suddenly felt strangely simplistic compared to all of the edgy commuters in the busy train station.

"You do look great Jen," Dan said stepping forward for his turn. When he hugged her, Jenny squeezed him tightly, taking in his scent. She had missed her big brother more than she realized.

"You too Dan. Protesting barbershops I see," Jenny said when they broke apart.

"Very funny. I'll have you know longer hair is very in right now." Jenny and Rufus both shot Dan a quizzical look. "Nevermind."

"Okay, you two," Rufus interjected. "As much as I've missed your banter, the van der Woodsens are waiting for us so let's get your bags and get out of here."

"Sounds good," Jenny replied. She tried to sound excited but she could feel her anxiety rising.

Dan, seemingly hearing her thoughts, reassuringly grasped her hand as they headed towards the luggage area. At least distance hadn't dulled their psychic link, Jenny thought, as she clung to his hand like a lifeline.

"Just promise you won't leave again, okay?" Eric mumbled, his face pressed into Jenny's shoulder. He had been hugging her for close to three minutes now and his death grip was making Jenny lightheaded.

"Okay Eric. I promise, alright? Can you let go now?" Jenny responded, pain in her voice. Eric shook his head.

"Alright Eric that's enough. Give Jenny some breathing room won't you?" Lily said wearily.

Eric finally relinquished his grip and Jenny let out an exaggerated breath. She planned on looking annoyed but after months of phone calls and letters she couldn't keep the joy of being reunited with her best friend off her face. "I've missed you too," she said ruffling Eric's hair.

"Okay, watch the 'do," he responded stepping out of her each and smoothing a hand over his head.

Rufus and Dan chuckled. "It is wonderful to have you back Jenny," Lily said smiling warmly.

"It's wonderful to be back," Jenny lied. "Oh well," she thought. "No one will know." Dan tossed her a knowing glance. Well, almost no one.

Just then, the elevator dinged and Serena stepped out. She stopped when she saw Jenny. "Jenny, I forgot you were getting in today," she said. Her voice was neither warm nor cold, it just sort of…was.

"Hi Serena," Jenny said. An uncomfortable silence fell over the room.

"Well," Lily broke in, "I could use some help in the kitchen getting dinner together. Boys?"

"Don't you have a full-time chef?" Dan asked. Lily shot him a stern look. "I mean, I would love to help!" he said walking briskly out of the room followed by Rufus.

Eric didn't budge, his eyes darting between Jenny and Serena.

"Eric?" Lily asked.

"I'm good," he responded, now staring fixedly at Serena, doing his best impersonation of a guard dog.

"It's fine Eric," Jenny said, gently nudging him. He glanced at her, then back at Serena, before slowly turning and following Lily to the kitchen.

For a few seconds, silence hung between the two blondes. It was almost hard for Jenny to believe they were step-sisters and even harder to believe they had at one time been friends.

"Look, um, Serena, I'm really sorry about last year and how I treated you," Jenny said. "I really messed things up and I understand that you're probably less than enthused about my being back. I know I can't take it back and I don't expect us to be friends again or for you to even like me but I just need you to know that I am really really sorry."

Serena looked at the younger girl and smiled slightly. "It's okay Jenny. I mean sisters never really like each other right?"

Jenny smiled at Serena's attempt at diffusing the situation. She remembered why it had been so easy for her to like Serena in the first place. "Right," she said.

"Why is it so quiet in there? Is Jenny still breathing?" Eric shouted from the next room.

Serena rolled her eyes, "Now that you're back you can take my tactful little brother off my hands for a while," she said.

Jenny laughed as Eric and Dan walked in.

"What?" Eric asked.

"Nothing," Serena said. "I've got to get going, I'm meeting Blair for dinner."

"But I've prepared a celebratory dinner for Jenny," Lily said joining the group in the living room. "It's almost ready."

"You prepared it?" Eric asked, raising his eyebrows. Dan tried to suppress his laugh. Lily glared at her son.

"And…" Lily continued, "The charity gala is this evening and I'd like us to go together, as a family. It will be a great way to let our friends know Jenny is back home."

"Actually Lily, that was really nice of you but I'm beat. I think I'd just like to unpack and relax a little bit," Jenny replied. There was nothing she would like less than going to an Upper East Side gala on her first night back in town.

Lily was about to protest when Rufus stepped in. "That's understandable sweetie. I put your bags upstairs in your new room. Do you want some help unpacking?"

"Actually," Jenny began, "I wanted to talk to you about that." This was a moment she couldn't put off any longer. "The penthouse looks great and everything—"

"Thank you," Lily said, "Just wait until you see the size of your new closet."

"But," Jenny continued, "I was thinking I would actually rather stay at the loft with Dan."


"Jenny…I don't think that's a good idea," Rufus said warily.

"Look, dad, I know I wasn't exactly responsible last year but you don't have to worry about that this time, okay? I just—I just don't…" Jenny trailed off. She couldn't exactly articulate that being around all of this high society stuff was toxic for her. Like being an alcoholic living above a bar. A bar with free booze.

Dan interjected, "I would be fine with me. Really fine actually. It would be nice to have to company…and someone to make me a sandwich every now and then."

Jenny elbowed her brother in the stomach and Rufus let out a small laugh. "Okay," he said uneasily. "We can give it a try. Tentatively."

"Thanks dad!" Jenny said hugging her father. "You won't regret it." She was so relieved.

"Jenny, are you sure I can't convince you to come to the gala?" Lily asked.

"Maybe the next one mom." Eric answered for her. "It's not like we have shortage of them around here."

Jenny paced around the loft. She had finished unpacking two hours ago, Dan had left for the gala one hour ago, and Eric hadn't called to check on her in a solid thirty minutes.

The loft was exactly how she remembered it. Records lining the living room wall, the smell of countless cups of coffee hanging in the air. In a huff of restlessness, Jenny threw herself down on the couch and stretched out. She wasn't exactly bored, just unsettled. She couldn't believe she was back here. Had it really been less than a year? It seemed like a lifetime ago. A lifetime that she would rather forget. The great thing about her school in Chicago was that there were always people around. Seldom was she left alone with her thoughts like she was now. These moments were when the darkness started to creep back in. When she felt that loneliness and self-loathing for the person she had become and the things she had done last year. She had told herself she was different now but she knew that wasn't how everyone else would feel. And what if they were right?


Jenny's thoughts were interrupted by her stomach. In all the unpacking (and self-deprecating) she had forgotten to eat something. She stood up and walked to the fridge, opening the heavy door. Cheese, a half-eaten sandwich, and hot sauce were all that greeted her.

"Great Dan," she said, slamming the door shut. "Welcome back to living with a boy."

She grabbed her wallet and coat and headed out the door. At least she had an excuse for eating some junk food.

The walk to her favorite Thai place was chilly. She forgot how the temperature could change from day to night in the city. She picked up a steaming bowl of chicken pad thai and tipped the cook. She pushed the door open with her back a spun onto sidewalk. She walked a few steps, focusing on putting her change back into her wallet, when she slammed into someone, spilling coins everywhere.

"I'm so sorry," she said, not glancing up. "I wasn't watching where—"


Jenny froze. She knew that voice but wasn't ready to hear it quite yet.

"Nate. H-h-hi. Sorry I didn't see you." She stood up and they faced each other awkwardly.

"Dan told me you were coming home for the holidays," Nate said, rubbing the back of his neck. "When did you get in?"

"Today," Jenny said, "Just a few hours ago actually." Nate nodded.

It would have been easy to ask how he was, listen to his answer and then reply with something about her food getting cold and make a quick escape but Jenny knew that wasn't the right thing to do.

"Listen Nate, I never apologized to you for last year," Jenny began.

"Jenny, you don't have to—"

"No, I do. You were my friend, a good friend, and I took advantage of that. I'm really sorry…about everything," Jenny said meeting his eyes for the first time since they bumped into each other. They were just as bright and clear as ever.

"It's okay Jenny," Nate replied.

"No it's not, but thanks for saying that," Jenny said.

They stared at each other for a moment. Nate was taken aback by how normal she looked, like the Jenny he had spent the night talking to years ago, on Blair's birthday. It made him wonder how different he looked now, from the boy he was.

Jenny broke the silence, "Well, I should get going before my food gets cold. I'll see you around Nate." She said turning to leave.

"Wait, aren't you going to Lily's gala?" Nate asked.

Jenny looked down at her outfit, now complete with a pad thai stain, and smiled. "No, that's not really my thing."

Nate looked at her, confused. "Since when?" he asked.

"Since ever," Jenny replied. "It just took me a while to realize it." She smiled and walked away.

Nate stayed still for a beat watching her go before pulling his coat tighter and heading the opposite way.