Set during S04E09 episode The Witches of Bushwick. Nate mistakenly kisses Jenny for the second time at a masquerade party, thinking she is Serena. Only this time, he knows better.
Part 1
Something was wrong, Nate could tell. She looked like Serena and she smelled like Serena, but it didn't feel like her. It felt like...
"Jenny!" Nate called. The girl paused for a split second before continuing to walk away from him. Their whole plan would be ruined if she gave away who she was. She needed this to work; she needed to come back to New York City.
She did her best not to look behind her, which is why she didn't know he was too close until it was too late: he'd turned her around and ripped off her mask before she could even realise it was happening.
Nate looked at her, confused, then quickly looked around to make sure no one had seen her. He gave her the mask back and she put it on before a dragged her away to the elevator. As soon as she saw where they were headed, Jenny stopped. Nate pulled on her arm, but she resisted.
"Please, Nate, I can't go up there," she talked quietly with desperation in her voice. Nate had seen her be many things, but desperate had never been one of them. She could be defiant, vulnerable, angry, sad, or scheming, but desperate? He didn't know how to feel about that, but a voice in his head reminded him of everything she'd done recently, and he didn't know if she deserved his compassion.
"You want to do this here in front of everybody? That's fine with me! What are you doing here, Jenny?" Nate asked.
She looked down, unable to answer him. She knew if she did, she would end up spilling everything to him and she couldn't do that to Vanessa and Juliet.
"Are you in the middle of some kind of plan again? I swear Jenny, if you are..."
"So what if I am? What am I, some kind of doormat? People can hurt me, ban me out of this town but I can't do anything about it? Do you know what this has been like for me, Nate, the hell that I've been going through? I can't come visit my family, my mother doesn't really want me to be there, and I lost some of my best friends, including you, by the way. And for what? Because I felt so alone and abandoned that I slept with Chuck? Tell me, what's so unforgivable about that?"
Nate felt like she'd punched him in the chest and he'd run out of air. He knew, of course, that Jenny and Chuck had slept together, all of the Upper East Side did. But hearing her say it out loud like that, it did things to him he hadn't expected. When he didn't say anything, Jenny turned around to walk away. He grabbed her arm again to keep her from leaving, but it was different this time, more gentle. She looked back at him but Nate couldn't tell what she was feeling because he couldn't see her face with that stupid mask on.
"Let's talk about this. Like adults. Just please, call off whatever you're planning," Nate begged, and Jenny sighed.
"I can't, Nate, it's too late. Besides, I'm not sure I want to," Jenny said.
"If it's going to hurt my friends, Jenny, it'll hurt me too. Please, do it for me."
She looked down again and took out her cell phone. She texted both Juliet and Vanessa.
"I can't guarantee what happens from now on," she said.
"I know," Nate replied, "but thanks. Let's go somewhere we can talk more privately, now." He tugged at her arm again to take her to the elevators, but she resisted.
"I can't go up there, I told you," she said, referring to Chuck and Nate's penthouse. Nate ran his hand through his hair, feeling like a jerk for offering to take her to the place that held such an awful memory for her.
"Come on," he said, and he led them outside. There was a cab waiting there and Nate opened the door, gesturing for Jenny to get in first. Nate told the driver the address of his apartment and they rode in silence for a while.
"Can't you take your mask off, please?" Nate asked. He wanted to see her face, see her eyes, to know what she was feeling. Jenny took the mask off slowly, and Nate noticed she didn't have on any of the heavy makeup she usually did. Her natural beauty always did something to him, something he couldn't define. He liked her most when she was bared of all those useless accessories, which was one of the reasons why he had loved living with the Humphreys for that little while. He got to see her first thing in the morning, when there was still sleep in her eyes and her defences weren't up yet. She was just Jenny, a daughter, a sister, a friend. She laughed more easily when she didn't have makeup on, he noticed. He knew it was weird, but that was Jenny.
Jenny didn't know how to feel anymore. One of the reasons she regretted leaving the Upper East Side so much was that she didn't get to hang out with Nate anymore. Even during the times when they weren't close, she would at least get to run into him every once in a while. And now, sitting in that cab, her senses were overwhelmed by him. His smell, the feel of his leg pressed against hers, the sound of his breathing. She burned the moment in her memory knowing that whatever would happen, she and Nate would never be together. He could never have feelings for her after what she had done.
She thought, after she slept with Chuck, that she would be able to forget about Nate. Not because she had any feelings for Chuck, but because it meant that Nate would never forgive her. She figured if she trashed all her chances with him, she'd be able to convince herself to move on because she had no choice. However, it turned out she'd been wrong. Sleeping with Chuck had only made her feeling for Nate stronger. She realised how much it hurt her to hurt him, and it proved impossible for her to accept that she had no chance of ever being with him again. She had thought just being his friend was too difficult, but she had no idea then how much it hurt not to be in his life at all. Now she knew, and it seemed to be all she thought about. When she would lie awake at night she'd relive all their precious moments together, and even though it seemed like it hurt more every day, she couldn't bring herself to forget about him and move on. His mark on her heart was indelible, and she was slowly beginning to accept that she'd never be over him.
They didn't speak for the rest of the cab ride.
