To Jenny Humphrey…

I want you. I want to be with you. I really care about you. I don't know what to do.

-Nate

Being in a state of chronic stress was leaving Nate Archibald frazzled and emotionally injured. He had never felt more vulnerable. The world that had given him the most loyal of best friends, a plethora of privilege, and an out right genetic jackpot had now come to deliver to him a lifetime of misery that he had previously been spared from.

He had just been kicked out of the Humphrey household and the hiatus of anxiety he had been feeling had abruptly ended. There was a miniscule time frame where he was happy again; comfortable- even hopeful. The knowledge that he had betrayed Dan made Nate wince inside because he knew that Humphrey had showed him true selfless compassion.

Despite the issues it caused though, he simply couldn't make himself regret the brief moments he had with Jenny. For a year, Nate had run around in circles after different girls. His feelings were always intense but they had a tendency to hop from woman to woman. Somehow, dipping into the possibility of having something with Jenny rang different than anything else he had experienced before.

Serena held the seduction of a fantasy almost grasped in reality. He had harboured a secret attraction to her for years but in the end there had been nothing there but friendship and lust.

Blair was the first person Nate loved. She was the dependable one at his side through everything. But once they both woke up from the façade of perfection the relationship emitted, it became clear that people can't just go through life settling for just stability.

Vanessa was Nate's saviour from the drudging mess that was the Upper East side. She was refreshing and their relationship was playful and easy…but he hadn't felt anything real from it. It was a fling that cleared his mind from his messy break-up but it offered no possibility of something long-term. He couldn't honestly see himself falling in love with her.

Every other girl had caught his eye almost immediately. Every one of them had embedded in him a prick of interest. They were all in a sense pre-planned, pre-considered. Jenny wasn't in the slightest.

She was the innocent underling of his girlfriend. She was the little sister of a friend of his. She was adorable and witty, interesting and sincere. But she was just Little J.

It isn't that a two year age difference bothered Nate- the gap was slight and he certainly would not have said that dating a sophomore was out of the question. He just never thought about the girl that way. He had always been protective of her, concerned. He had seen in her a girl he could trust and someone he could be completely himself around. When he moved in with the Humphrey's, he wasn't allowed to just see her as a little girl any more. She was beautiful and boldly mature. And he cared about her intensely in a way that had him fiercely wanting to have some claim to her.

When she asked him why the hell he cared so much, the question woke him up. She was right. He wasn't her brother, he wasn't her boyfriend… And one day he realized with a jolt that it wasn't just brotherly concern he had for her. When he walked in on her shirtless and dancing in front of some sleazy photographer- he didn't want to save her because she was young and needed protecting; he made her leave because he couldn't bear to see her taken advantage of. He was jealous of every guy that could see her in that light, that could have her affection.

And then she kissed him and he just had to wonder why the hell couldn't he be with her?

It was a ridiculously bad time for a relationship. He was living with her thanks to her older brother's hospitality. He was homeless, penniless, and at the mercy of the very protective Humphrey men. She was breaking free from her submissive role as the good daughter who did just as she was told and experiencing raw high-stakes drama for the first time in her life. There was precious little time to even think about something like this…

It had felt amazing to see her face filled with undiluted glee as she jumped into his arms and pressed her lips against his after her successful guerrilla fashion show. The moment was all the two would have. In his muddled state, Nate had forgotten about one other important issue in why he and Jenny shouldn't be together- his ex was one of her best friends.

From the look on Vanessa's face, Nate knew she wasn't over him. From the look on Jenny's, he also knew Jenny wasn't Chuck and she would not be able to choose a love interest over the feelings of a close friend.

Knocked on his ass, Nate had nothing else to do but lay low. It hardly seemed like anyone even gave a crap about him.

In his vulnerability, it still stung like nothing else when Jenny ignored his multiple paged letter. He had opened his heart out and told her every shameless feeling in the hope that she would not shut down the possibility of them before it even had a chance to grow. He had told her how much he cared, he had told her how lost he felt. And she had left him lost.

At the end of the day, he had to forcibly swallow the fact that she had probably just harboured a shallow crush on him and didn't want anything more from him. She was busy, she had troubles of her own… she didn't have time and she probably didn't even care that much.

So at the end of the day, he did what he always did. He shrugged off the disappointment and accepted the first girl who expressed interest. This was what he did. He licked his wounds by diving headlong into something new with another woman. Smiling at Vanessa's hesitant attempt to tell him she still cared, he did what he did best- accepted an unchangeable fact (that Jenny wasn't interested anymore) and walked through the new door that had been opened for him.

He had jumped from Blair to Serena, back to Blair, from Blair to Vanessa, and from Vanessa to Catherine and back to Vanessa. It was who he was. It was what he did. But as he watched Vanessa walk away grinning after he asked her out again, he couldn't help but think that he had left Vanessa twice for a reason. Shoving thoughts of Jenny out of his head, he walked back into his newly restored house. A lost cause was a lost cause.

xXx

Hold your breath
'Cause it's all you get
To see this through
While i try my best
To get over you

xXx

On the other side of town, Jenny laughed with her family, completely carefree for the first time in months. She was home, she was loved, she was happy. But a tiny part of her feelings fell when she thought about the fact that Nate had just walked out without a word; that he hadn't tried to contact her after she ran after Vanessa. Maybe he was only interested in her because it was convenient and she made it inconvenient- making him move on. Truth was, she had been liked him just a little ever since he kissed her that night last year at Blair's masquerade ball. Truth was, she had wanted to feel his lips on hers ever since.

Truth was, Nate was the first guy Jenny had ever kissed. And she was everything she could have asked for. But she was fifteen… who was she kidding? He had been with women, not girls. Women who were gorgeous and experienced.

She would move on. He seemed to.

xXx

On the other side of Jenny's table, Vanessa smiled at the girl as she pushed Nate's love letter further into her purse. So what if stealing it was wrong? He had asked her out just a few hours ago, so clearly he couldn't care that much about Jenny and Jenny didn't even seem to care about him. Vanessa had held feelings for him for months. She ignored the fact that Nate's letter directly proved he cared about Jenny quite a lot. Swallowing the pain and the guilt and the jealously, Vanessa feigned friendship as she did the first truly treacherous thing in her life.

xXx

One day soon, Nate and Jenny would run into each other again.

On that day he would tell her that it was okay that she didn't answer his letter.

On that day, she would tell him that she had only just moved back into her house after being moved out for weeks.

On that day, she would tell him she never received his letter.

On that day, Nate would softly tell her what the letter said.

On that day, Vanessa would crumble again because Jenny would tell him that she feels everything he feels for her and more.

And he would take her hand and know that for the first time in his life, he couldn't move on quite as easily as he always used to. And she would lean into the kiss he initiated and think about how purely glad she was that neither were nearly as flippant as they tried to believe.


AN: Hey all, this is my first Gossip Girl fic. I've always been interested in Jenny/Nate and I was really giddy when the show started steering in that direction. Since I have the vague feeling it could be a while (if ever) for us to get some real Jenny/Nate romance on the show, I wrote this. I just watched 2.11 and had to do it. Haha this ship and that episode actually brought me out of fanfiction writing hibernation- I haven't written anything in months.

I love reviews! Let me know if you guys think I should continue this or if you'd be interested in reading more about Nate/Jenny :)