An alternate ending to season three.

Chapter 1

Jenny hurried into Nate's apartment suite at the Empire Hotel. This was it- rock bottom. Her own father wanted to kick her out of the house. She had worked so hard to fit in on the Upper East Side, she ended up loosing herself, and now she had nothing to show for it.

The only thing that kept her going was the hope that her earlier scheme had finally put an end to Serena and Nate's already stumbling relationship, and she imagined finding Nate in need of comfort, which she would be more than happy to give.

Unfortunately, she only spotted Chuck hastily filling a suitcase with a colorful array of clothes. His usually styled hair was messy, chaotically falling into his face, which held an expression Jenny was unable to read. Hurt? Anger? Confusion? Surely Chuck Bass was incapable of these mere mortal emotions. Quietly moving behind a column to avoid being seen, Jenny watched the man who she had always held a strange fascination for. Chuck Bass was a character surrounded by myth, and very few people, maybe only Blair, Jenny guessed, actually knew what he was really like. This gave her an odd sense of intrusion as she observed him with his guard down, but still she found herself unable to look away, and before she even realized it she had moved away from her hiding place, and was walking towards her subject of interest.

"Humphrey?" Chuck looked up, not exactly surprised to see the girl who seemed to have taken up residency in his suite, but caught off guard by the mere fact that he was so focused on packing in order to get the hell out of New York after a devastating rejection from Blair, he had momentarily forgotten that other people existed.

"Hey," she let out nervously. Rarely did she feel so intimidated, but Chuck just had that sort of presence, which was magnified by the dark shadows that fell upon his angular face.

"If your looking for Nate, he's not here," Chuck stated while continuing the task at hand.

"Oh. Do you know when he'll be back?"

"I don't have the slightest idea," he said keeping his voice devoid of any emotion. He hated the idea of anyone seeing him so torn up and heart broken. He had a reputation to maintain after all.

Jenny felt that she should probably leave, but then remembered that she had nowhere else to go. "Ok, I can just wait in his room."

"If you want to make yourself a drink while you wait, your welcome to." Chuck worked to regain his composure, before studying the girl. He could tell that she was in a bad place, and figured they both could use an adult beverage. It was only polite.

Normally this offer would have been politely shut down, but Jenny thought that today of all days she needed a drink. "Sure," she replied, before she made her way to the bar.

"Here, allow me," he stated getting up to get her a drink.

"Umm, I'll take a rum and coke," she said, deciding that it was best to just let Chuck help her, to which he let out an smirk, but Jenny could sense that there was more than just a hint of sadness behind his typically devious smile.

Chuck made her her drink, and poured a glass of scotch for himself, before they both leaned up against the bar to watch the sun begin to set on the New York skyline. They drank in silence, but for whatever reason it didn't feel awkward.

"Where are you going?" Jenny asked, breaking the noiselessness of the room.

"I'm not really sure yet," was Chuck's sullen response.

"It must be nice to be able to just pack up and leave." she said feeling more comfortable with her company.

Chuck nodded. "New York doesn't seem to be offering me anything anymore." Chuck thought of his failed relationship with Blair, and his lack of family ties, and for the first time it really dawned on him that he might never becoming back. Usually when he ran away it was to blow off steam, but he always knew in his heart that it was New York where he truly belong. There was always something calling him back, be it his fathers engagement, or a confession of love. Now he didn't know where he belonged.

"I know what you mean," Jenny said, reflecting on her own situation.

"Refill?" Chuck asked noticing Jenny's empty cup.

"Sure."

As the last of the sunlight disappeared from the city, Jenny realized that now might be a good time for her to disappear from the city as well. Blair was right, everyone hated her, and she had no business showing her face in Manhattan anymore.

"Take me with you." The words sprung out from her mouth with out much thought as she was beginning to feel a bit tipsy. It was a last minute plea, and although she knew Chuck probably wouldn't want his little stepsister, or whatever she was, tagging along on his travels, she still felt the chance of escape worth a shot.

"What?" he replied, truly taken back by her request.

"I need to leave."

"I'm not going to take you with me."

"Why? I'm not just that naive little girl anymore. I'll be able to handle whatever you do."

"I never said you where naïve, in fact I find you to be quite clever for a girl from Brooklyn."

"Then take me with you," Jenny begged.

Chuck took a good look at the girl. She had proven herself to be intelligent and cunning, maybe she would make a good partner in crime, but she always let her desperation ruin her, and she would never be able to keep up with his debauched ways. Still he wouldn't mind having company, and in the back of his mind he could think of no better company to get back at Blair for breaking his heart.

"I'm leaving in less than an hour. You don't have time to pack. We will just have to buy you stuff when we get there. I'm thinking Prague."

Jenny nodded. She had no idea what she was about to get herself into.

Tell me what you think.