Author's Note: I know it's been awhile since I've updated this fic, but let's just say I got my mojo back. I've got quite a journey planned for the Humphrey's. I know this is an AU verse. DS is still very much canon and sort of mirrors what you saw in the show (at least the first season) with my own additions to the story. But Brad's journey is kind of a risk and I've always wanted to write D with a brother. I still love J and she's one of my favorite characters, but this is an AU verse. It also affects the version of Dan that you will see. He still has his confidence, but he is still very much a younger brother. Now that I've bored you with this insanely long author's note, here is the latest chapter.

The Lesser Humphrey

Chapter 6:

Dan was standing in front of the bathroom mirror dabbing the spots where he'd nicked himself with the razor when his brother came barging in. Brad closed the door and lit up a cigarette. Dan grimaced and said, "Can't you do that somewhere else."

"Nope."

"It's a disgusting habit."

"So is your face."

Dan rolled his eyes and went back to examining his face. He could feel Brad simmering quietly. Dan was used to the drill. His brother with sit there silently pouting and he'd ask how he was doing, but he just wanted to get ready for his date with Serena.

"What is it?"

Brad took another drag from his cigarette and said, "me? There's nothing wrong."

Dan pulled the cigarette from his mouth and put it out. "First you only smoke when you're upset. You're also sitting there doing that silent pouting thing that you do. So, I know you want to talk about it, so spill."

"It's been a week dude. It was one comment. Don't you think she's over-reacting?"

Dan looked at his brother with confusion. "Who are you talking about?"

"Vanessa"

Dan looked at him and smirked. "You like her?"

"I do not like her. I just think she's being unreasonable."

Dan started to laugh. "Brad Humphrey, Ladies man likes Vanessa Abrams."

Brad rolled his eyes. "I'm not having this conversation anymore. It's totally unproductive."

Dan followed his brother out of the bathroom and into his bedroom. This was a moment he wasn't going to pass off especially after years of him ribbing about Vanessa's crush on him. "So when? When did this happen?"

"I have no idea what you are talking about. You're over-reacting dude. You're making too much of this."

"hmm so why is her silence bugging you so much?"

"It's just, it's unreasonable."

Dan laid a hand on his shoulder. "If you say so, but if its bothering you so much go talk to her. Anyways, I gotta go Serena is waiting for me."

Brad watched the smile on his brother face and patted him on the back. "So have you made past first base yet?"

"Shut up."

"I knew it. You're doomed to be a virgin forever."

"And you're doomed to be an asshole forever."

Brad stood on the street facing Vanessa's building and stuffed his hands in his pockets. He couldn't remember the last time he'd been over here. She lived here with her sister who spent most of the time on tour. He pushed open the door and pressed the button. "It's me V. Buzz me up."

"Go away,"she said.

He leaned against the wall and spoke into the intercom. "Stop being stubborn. Just buzz me up. I promise I'll be nice."

Vanessa sighed and buzzed him. She wasn't mad at him anymore, but she was damned if she was going to let him know what was going on with her. She'd had enough of the Humphrey's self-righteousness. It was bad enough losing Dan to Serena, but it wasn't really that much of a shock. He'd always had a soft spot for her, but she couldn't forgive Brad's cruelty. He was always the one person she could be herself with and she never expected him to be so cold with her. She was used to his snarkiness, but there was always a difference between their little back and forth and being cruel, but h didn't seem to understand the difference. She lit the candle that had gone out and wrapped the blanket around her tightly.

She got up and walked to the door when he knocked loudly. "I'm coming." She opened the door a crack and said, "you have five minutes."

"Jesus woman, let me in. Since when are you so over-sensitive?"

He pushed his way past her and looked around the dimly lit apartment. There were lit candles all over the apartment. "You expecting someone?"he said with a frown. So was that why she was being so weirdly defensive. She was hiding some dude. He wasn't sure he liked that. He was probably some pompous ass who was even more pretentious than his brother except Dan actually was genuine. He loved all that arts crap. He imagined this was some smooth guy who liked to use his knowledge of art in an effort to get into girls pants. He probably had bangs too ugh.

"What? No. What do you want Brad?"

"You're hiding something or someone? Who is he? I believe I owe him an obligatory grilling. Tell the slimy hipster he's got to go through me to do my duty."

She rolled her eyes. "There is no one; just me. I thought you were eager to be rid of me?"

"I came over to apologize, but you are being evasive and crankier than usual. Plus what's with all the candles and the blankets."

Brad reached for the light switch and tried to turn on the lights, but they weren't working. "How long have you been without electricity?

"A day or two," mumbled Vanessa.

"Get your stuff you're coming with me," he said as he guided her by the arm and led her into what he presumed was her bedroom. He picked up a sparkly top and threw it on the bed. "Sparkles?"

"That's my sisters."

"Figured. Not exactly your style."

Vanessa rolled her eyes and said, "My style? You sound like one of those pansies you go to school with?"

Brad just raised an eyebrow and stuffed bunch of random items into a duffel bag he found on the floor. "What are you doing? Stop touching my stuff. You can't just barge into my house and tell me what to do."

He looks up at her a beat and says, "I can and I will."

Meanwhile Dan waited in the middle of Central Park for Serena to arrive. He checked his watch every five minutes. She was late which shouldn't surprise him, but he really wanted this surprise to go off without a hitch. It was a warm fall afternoon and the weather was perfect for what he had planned. He laid out a blanket and he'd brought a long some sparkling cider as well as some sandwiches and fruit that he'd put together. He was staring at his watch for the fifth time in the past twenty minutes when he saw a flash of golden hair. She was running towards him in her high heels and a huge smile on her face. Serena nearly knocked him over when she embraced him. "I'm so sorry I'm late,"she said breathlessly.

"It's okay. I'm just glad that you came," he said.

Serena crinkled her face in confusion, "why wouldn't I?"

"Ugh no reason. Just being silly. Anyways your picnic awaits me lady,"Dan says as he bows. He takes her hand and leads her to the blanket. Serena is smiling and laughing so brightly that he swears her happiness is infectious. He's always been more of a brooder, but something about her just puts a permanent hop in his step. Dan reaches for the sparkling apple cider and pours it into the glasses he has brought along. He hands her one and makes a toast. "To the sweetest and prettiest girl in all of New York no the whole world."

"Stop you're making me blush."

"It's true. You're amazing,"Dan said as he leaned over and kissed her. Serena pulled him closer and wrapped her arms around him. He made her feel safe, loved. Something that she wasn't really used to and it scared her. She had just come back from Blair's again. Serena wanted to make things right, but she knew she couldn't make up for what she'd done.

Serena held a bottle of champagne in her hand as she twirled to the sound of the music. Nate reached for her pulling her down on the poor as she giggled. She spilled the champagne over them both and they both broke into a fit of giggles. Nate pulled her on to his lap and kissed her. Serena lost her self in the moment. She felt free and a part of her had liked Nate. Afterwards, she pulled on her clothes and ran into the city streets with tears streaming down her face. She just had to keep moving. Serena had crossed a line that she could not uncross.

Serena shuddered when she remembered that night. It went from bad to worse, but she was a different person now; a better person. If Dan ever discovered what she did, she'd lose him and that was something she wasn't willing to let happen. Dan can feel the shift in her mood. She's gone from happy to sad in an instant which doesn't really surprise him, it just makes him worry. He holds her face in his hands and says, "What's wrong?"

"Nothing," she responds as she attempts to cover the sadness with a smile, but Dan can see through it. There is an infinite sadness in her eyes and all he wants to do is to make it go away. "You can tell me. I know something is bothering you."

"I'm fine. I just had a fight with my mother."

Dan drops his hands in disappointment. He knows she is lying to him. He can feel it, but he also knows that can't force her to trust him. So, he drops the subject for now. They go back to their picnic and Dan tells her about how his father has been going on all of these dates with these strange women.

"Does it bother you? Your father dating?"Serena asks as she pops a grape in her mouth.

"I don't know. Things have been weird between my mom and dad for awhile, Brad thinks they're both beign stupid. But, I don't know what to think. It's not really any of my business."

"You're a sweet, but it's got to be weird watching your parents split. I was so young when my father left that I've gotten used to my mother and her parade of jerks."

"Has she remarried a lot?" Dan asked softly.

"She's been married three times. I just wish that she cared more about Eric and I, but you can't choose your parents,"she said nonchalantly.

"But, that doesn't mean they have a right to act like assholes,"Dan muttered. He was seething on her behalf. Serena gave him a look of warning and he knew that he'd overstepped an invisible line. "Sorry, I just can't understand how anyone can have you in their life and not treasure that."

Serena smiled and wrapped and pushed him down on the blanket.