Author's Note: This chapter is a set up for upcoming chapters. Yeah, I know longest filler chapter in history

Chapter 6: Owner of a lonely heart

Dan walked through the city streets after leaving Serena's place haunted by a familiar feeling: he'd taught himself to live outside of his emotions unless it had to do with his writing. In a span of a month, he'd started to feel those emotions creeping back and he was struggling with how to deal with the pain and hurt and frustration he felt which he avoided for years. Ten years later, he was breaking his vow of exposing himself to the pain he felt the first time he lost Serena and it was ripping him up inside. Dan could hardly believe he'd allowed himself to get sucked in once again. What was he thinking? He should have kept everything strictly professional because with Serena things were never uncomplicated. Dan sat on a bench in the park and just looked around him trying not to relive the past.

Dan watched her, as he stood on that stage poised and ready to wax poetic about his years at St. Jude's. The two schools had decided to do a joint ceremony, but his words felt empty. Later as his classmates posed with friends and family he stood there in the courtyard watching her, debating whether he should go up and speak to her. It had been 3 months since they had broken up and 2 months since they had last spoken. All he wanted was to go up to her and shake her and beg her not do this; not to give up on them. Instead he just stood there and watched as she posed for a picture with Blair. Her smile was bright and somehow things had gone back to the beginning. He was lonely boy again and Serena was the IT girl surrounded by her friends. If it hadn't been for the fact that their parents were dating it would be like the last two years had never happened.

"Stop pouting Dan. You should be happy,"Jenny said as she tugged on his arm.

"Where are you taking me?"

"Time for you to smile for the camera and be the dutiful son again,"she said.

Dan sighed and followed his sister to where his parents stood. Rufus had his arm around lily and Alison stood next to them stiffly. Dan could only imagine how awkward the whole experience was for her.

"There he is. My son the graduate, "Alison beamed as she hugged him. Dan hugged her back. He was happy that she was hear, but he felt disconnected to the woman who had raised him. In fact, he felt disconnected from everything lately. All he wanted to do was fast track through the next few months. At college, he could reinvent himself. All Dan wanted was a fresh start. Dan posed for pictures that he would probably never look at again and waited for this torture to come to an end. He was standing between Lily and his father when he saw her approaching them. His heart nearly stopped. She was beautiful and all he wanted to do was wrap his arms around her.

"There you are, Serena. Come on get in the picture, "Lily insisted.

Serena smiled and stood next to her mother as Jenny took a picture of the foursome.

"Jenny, give me the camera. Dan stand beside Serena. Time for a picture of the graduates," Rufus said. Dan could hardly believe this. How oblivious could one person be to the pain he caused. Wasn't it bad enough that he was the reason that he wasn't speaking to Serena?

They stood together with painfully awkward smiles on their faces. Dan knew this was his chance to say something, but every time he tried to open his mouth the words refuse to come. For the first time in his life he was speechless.

Nate sat on Eric's grey couch wringing his hands. He had no idea how to say what it was he wanted, no needed to say. He finally looked up at Eric. He didn't really know him and it was more than a little awkward for him to be coming to him with this info, but he really didn't know who else to go to.

"I know this will sound a little weird and you're probably wondering why I'm coming to you with this."

"What is it, Nate?"Eric asked softly.

"I think I might be gay."

"Wow! So, not what I was expecting,"Eric said.

"I'm sorry. I just didn't know who else to talk to. I'm just so confused."

Eric smiled and said, "you want some coffee because I need some coffee."

"Sure,"Nate said ad he smiled at him. He ran an errant hand through his hair and wondered how his life had shifted so quickly.

"So, why don't you start from the top and I promise not to judge you. I understand the turmoil you must be going through. I also remember how it felt when I had no say in my coming out. If you don't want to say anything thats fine. Take your time and don't worry I won't tell anybody about this. You can trust me Nate.

Serena was really starting to wear out her collection of dvds since Dan had re-entered her life. His words earlier that day were still haunting her. She knew she should have been honest with him, but everything seemed to just get out of control and it was easier for her to keep up the pretence. It wasn't her wisest decision, but Dan had this way of frying her brain and making logic and common sense fly out the window. She was trying so hard to keep a professional distance from him that she managed to create even more drama.

"But, he was still an asshole," she thought to herself. She just wanted to go back to her quiet ordered life that didn't include Dan Humphrey. Serena wanted him to leave her alone, even though a part of her sough him out and wondered if they could ever work again.

"Don't be stupid,"she chided herself.

"You know talking to yourself is never a good sign,"Casey said as he leaned in the doorway.

"Hey,"she said as she smiled up at him.

He walked over to her and joined her on her plush sofa. He picked up her legs, removed her shoes and held her feet in his lap. As he massaged her feet, he asked "So, how's lover boy?"

"He's not my lover." she said as she lay her head back on the cushions.

"But, he was and will be again. I saw the way you two were looking at each other. Not even your fake marriage could stop the sparks that lit up that room."

"Well, he knows now and lets just say he wasn't too happy," she muttered.

"So, he's a drama queen too. Obviously, you're a match made in heaven or hell. I haven't decided which one yet," he said as he teased her.

Casey debated asking her about Nate. He wasn't exactly somebody she talked about. She'd made a passing reference to him, but he didn't seem like someone she knew that well with the exception of fuzzy memories from her teen years. He made a face and saw her studying him.

"What's on your mind case?

"Nothing."

"Stop lying. I know that face. It's the I wanna ask her something but I don't know if I should look."

"You know me entirely too well. What do you know about Dan's friend Nate."

Serena knew that another one had fallen under Nate's spell, but he was barking up the wrong tree. "Oh hun. He's straight."

"Are you sure about that? Maybe he doesn't know he's gay yet. I mean once you go Casey you just don't go back."

Serena's eyes bugged out. No, this could not be happening. "Are you sayin what I think you're saying."

"Maybe, I am. Now get off me bitch and give me the remote," he said as he flashed her a smile.

Dan was sitting in his loft later that afternoon still licking his wounds from earlier that day and the fact that Serena had lied to him again. He didn't know why it was bothering him so much, but it felt as though an old wound had been ripped open like it was fresh. He'd even managed to avoid all of his calls and the flashing sign that indicated that there was a message waiting for him. But, eventually he pressed the button and was surprised to hear the voice on the other end.

"Hey slut, how's it going? I heard you dumped your latest victim. I'm coming to town next month. I thought I'd drop you a line. In case you've forgotten who I am among your parade of whores its Jill. Beep."

Dan smiled and deleted the message. He'd call her back later. It had been years since he'd last seen her even though she had a bad habit of annoying him with random messages every few months. A part of him still regretted not being able to give her what she so desperately wanted. He knew now more than ever that there was only one person who would have that part of him.

October 2011, New Haven

Dan was sitting in the courtyard in the middle of the Old campus trying to finish his readings for philosophy class when a tall redhead with shiny curls came bouncing up to him. Her hair was nearly as vibrant as her personality from what he could tell. She was in his English lit class and they'd chatted a few times. He really had no desire to get involved with anyone. A year later and he was still licking his wounds from his last breakup with Serena. He had no idea how to get over a heartbreak that affected him so thoroughly. He felt emotionally retarded. He no longer had any idea how to deal with the opposite sex.

"Hey Humphrey. What are you reading?"

"Nietzche."

"How depressing. Do you ever do anything besides studying. You're whole emo boy act is really starting to get old."

"You barely know me Jill."

"Exactly. Get to it. Develop a personality, I know you know how to crack a joke or two."

"Are you always so forward."

"Yes."

"And you enjoy being pushy?"

"Like you enjoy being emo,"she quipped.

"Okay, I had that one coming. What do you have in mind?" he asked as he put his book away.

"Lets start with coffee and then you can pick me up tonight and take me to this kegger,"she said as she passed him a flyer.

"Uh I don't do frat boy bullshit."

"Don't be a downer Dan. Time to live it up," she said.

New Haven 2012

Jill was waiting for him in his dorm room. They'd been dating for nearly 6 months and she had snuck into his room to surprise him. She was setting the room up when she found the picture. It was still frame and was hidden in a door. She had a found it while she was looking for something to light a match with. He'd told her the sad tale about him and Serena and the minute she saw that picture she knew that had to be her. She was gorgeous and Jill hated her even more for this. So, she sat on his bed with tears rolling down her face when he came in.

"Jill? What's wrong? Why are you crying?"he asked as he kneeled before her.

She looked at him through tear-soaked eyes and flipped over the picture frame. It was a picture of him and Serena at the debutante ball. "Is this her?"she asked.

Dan was like a deer caught in the headlights. He really was trying to move on with his life, but he was over taken by anger. She had been digging through his things.

"What the fuck? Have you been looking through my things?"he asked sharply.

"I was looking for, no don't you dare turn this around on me."

"Jesus Jill. You were looking through my shit. We're going out, we're not married. I mean what are you even doing here?"he asked feeling the walls closing in on him. He knew in that moment that he could not do what she needed, wanted him to do. She wanted reassurances that everything would be alright that Serena was simply a part of his past, but he couldn't lie to her.

"Say something. Don't just stand their like a petrified idiot."

"I'm not afraid. I just, I don't know what you want me to say."

"Say something. Say you don't love her anymore. Say that you're over her. Say that I'm not wasting my fucking time. Tell me why you are stil have this stupid picture. She's always there. Atleast i can put a face to the name now,"she said in an angry diatribe.

Dan just stood there stunned. He was unable to do what she asked. He couldn't do what she asked because the truth would hurt so much more than silence he chose not to say anything.

Jill was seething. How was she supposed to compete with a girl he refused to let go of. She was like an enigma that haunted them both. Her anger was boiling to the surface and all she wanted to do was inflict pain.

"Fuck you. Fuck her. Fuck you both,"she said as she threw the frame across the room.

Dan was visibly stunned he bent down to pick up the shards of glasses and salvage what was left of his memories. He was seething. She had no right to try and destroy something that was his. She was saying something, but he couldn't hear her or he must have tuned her out minutes ago. Dan looked up at her silently and said, "Get out! Get out!"he screamed as he watched her storm out. He vowed in that moment that he'd never let anyone come close enough to destroy his memories ever again.