Are Chuck Bass and Lonely Boy friends? My sources say no, but I suspect they have a connection of some sort, and one that goes beyond sharing a cell. What could it be, you ask? My guess is it has something to do with a pretty girl or two. XOXO, Gossip Girl.

"He was just so silent, so sullen. After all those calls and that damn message for Blair he really had nothing to say. I mean, what am I supposed to think? Right?" Vanessa said as she sipped her caramel latte with extra whipped cream and chocolate shavings. Uncertainty in life made her diet uncertain as well. "Dan? Are you listening?"

Dan was staring out the window toward the New York Public library, as if waiting for someone to appear from its doors and run toward him. Vanessa wondered who he was looking for, wondered if perhaps Serena was inside or Rufus or Jenny. She wondered if he had been in the library and was longingly hoping to be back there now. Maybe she was talking about Chuck too much. When did she become that type of girl?

"Dan?" Vanessa said again, waving her free hand before his face.

Dan snapped out of his daze and turned back toward his friend. "Yeah?"

"I was talking and you were….well, doing that," she said pointing back to the window.

"Talking about Chuck?" Dan asked rolling his eyes.

"Hey, I remember you asking me about him. And I didn't hear you protest, just ignore me."

"Sorry. I have a lot on my mind," Dan said as his face suddenly went white.

Vanessa could tell he immediately regretted that last remark. It was an open invitation for her to ask him what specifically he had on his mind, what it was that plagued his thoughts. But she knew he did not want to talk about himself. If he had Chuck Bass would have been the furthest thing from his mind she was sure. Little did Vanessa know….

Breezing past his comment, Vanessa remarked, "No more Chuck talk. I promise."

"No, go on. Seriously," Dan said sympathetically.

Vanessa sighed. "I just don't understand what's happening. I forgave him, I forgave his father," she said, perking Dan's interest. "Ok, I told him I forgave him, which I guess entails Bart. And to be honest I'm not upset about that anymore. At least that was something that had purpose. As terrible as it sounds there was an end to that incident and here there's no end in sight."

Dan shook his head, but Vanessa doubted whether or not he understood.

She tried again. "I thought we were on the same page. Even if we aren't going to be…" Vanessa stopped, not knowing how to classify the romantic, flirtatious side of her relationship with Chuck. "I at least thought we would be friends."

"You are friends," Dan said. "You take care of him, after his father died you sat with him and talked with him. You listen and care about him."

"Yeah, yeah," Vanessa said, cutting him off. "Let's talk about something else. I think this is giving me a head ache. I'm trying to manipulate matter into scotch," she stated looking at her latte. Dan stared at it too. "It never works," she laughed.

"What is it with you and Chuck? Scotch is the aliment elixir of choice," Dan questioned. "You know it doesn't work right?"

"Ah, spoken by a man whose never had a good malt," she said sipping her latte slow and deliberately, as if it was containing the essential alcoholic nutrients she needed.

"Spoken by a man whose never had an imaginary malt," he corrected her.

Vanessa laughed. It was comforting to be back with Dan, comforting to feel comfortable again.

Her issues with Chuck still tugged at her heart and head. He had been so distant when they finally connected on the phone. She knew he wanted to talk to her, why else would he have called? Yet, it seemed as if there was something holding him back. It seemed there was always something holding him back. Still, she had asked if it, if she, was something worth pursuing and Chuck had said yes. There was a glimmer of hope mixed into heaps and heaps of confusion.

Time and time again, since the night he showed up at that run down bar to offer a promise of help, they had been playing a game of cat and mouse. It was a game that found them each taking the lead, then faltering, one after the other making a lead and then taking a fall. It was a game that seemingly had no winner.

Vanessa wondered if there was a winner, if a champion could be crowned, was it going to be her or Blair. No matter how much she wanted to ignore the obvious, Blair would always be in the picture. They were in some sort of struggle over the heart of Chuck Bass, but it was a struggle Vanessa never wanted to participate in. Sometimes she thought Blair revelled the challenge, loved the competition, and got off on the verbal and physical torment she laid into Vanessa. But as the days grew longer Vanessa realized they were very much alike. Perhaps Blair hated it as much as she did, perhaps Blair too was preserving her feelings, but not with funky clothes or the Brooklyn Bridge or even a trip to Connecticut. Perhaps it was Blair's seemingly surly behaviour, her mischievous ways, that saved her from the hurt that surely came from knowing Chuck Bass.

As Vanessa sat there wondering, pondering such questions, she realized she had been in that position before as well. She had felt sympathy for Blair and felt both anger and lust for Chuck. But she wasn't sure if she had actually felt love. And for that reason she decided…finally decided what to do.

"I have to go," she suddenly announced to Dan.

"What?" he asked as she stood up and put her coat back on. "Where?"

"There's just something I have to do," she stated heading to the door.

"V. wait," Dan called after her. "There's something I have to tell you."

"Can it wait until later?" she asked, her back tuned to him.

"I don't think it can," he said in return.

Vanessa turned back, a look of concern in her eyes. "What is it?" she asked, her voice filled with care.

"Are you going to see Chuck?" he asked.

Vanessa shook her head, but she wasn't signalling a negative response, merely confusion about how Dan was able to deduce such movements given her previous statements.

"I don't think you should," Dan began. "I don't think you two…"

"Stop." Vanessa held her hand up to his mouth and cut off his words. "If you're about to tell me that Chuck and I don't belong together or that I could get hurt or that I'm making a mistake I've heard it before. It's all I ever hear inside my own head."

Dan smiled, seemingly believing she had heard his plea and was about to take his silent advice.

"Dan, I'm a big girl. I can take care of myself," she said squeezing his shoulder, "But thanks for the concern."

Before Dan could say anything else, before he could convince her otherwise, she was out the door, heading away from the library and into the arms of someone Dan was sure she should avoid.

Chuck stood in the apartment Lily had graciously allowed him to move back into. He had just returned from his covert meeting with Dan Humphrey. He hated to admit it, after trying to change his image and retain his rights to his father's company, but scheming and secret keeping were among his favourite activities. He felt a rush after putting a plan into motion.

Lily, Eric, and Serena were all out. That was not unusually, given their newly hectic social lives, but the apartment felt empty, even as he stood in it. Somehow Chuck had become accustomed to having family around, although he would never tell them that he appreciated their company.

In the apartment, all alone, Chuck took off his suit coat and loosened his tie. There was no one around so he wasn't as concerned with appearances and ran his fingers through his perfectly coifed hair making it messy and free. Kicking off his shoes Chuck let himself into the kitchen and grabbed a bottle of water just as he heard the elevator reach his floor. He peered out from around the corner and watched Vanessa enter the apartment and turn toward him.

Chuck was startled to see her and it was clear all over his face this act was unexpected, even for a man who expected the unexpected.

Vanessa said nothing, did nothing. She simply stood there, looking at him, as if waiting for him to make the first move. Normally Chuck would have that move already underway, but this brazen attempt on her part left him temporarily immobile.

Just as he opened his mouth Vanessa walked toward him and for the second time that day placed her hand on someone's lips and prevented speech. With Chuck unable to speak, unwilling to speak, Vanessa took hold of the opportunity and moved in. She grabbed his pink, silk tie in one hand and pulled him close, her other hand moving from his mouth to the back of his head. Her fingers played with his newly relaxed hair, twirling the loose ends playfully as both her lips and eyes smiled up at him.

Vanessa's tongue slowly, seductively, moved across her bottom lip. The cherry lip balm made no move, somehow stained to her skin, but it did not matter for that was not her intent. She was simply baiting him, waiting to see if he would do what she had wanted him to do for days now, for weeks, for what felt like ages. A random black curl fell in her face and Chuck, on instinct, brushed it away with his hand, tucking it gently behind her ear. Vanessa knew she had him. This was the moment, all she had to do was wait.

Suddenly the clock in the apartment rang out, signalling a new hour. Chuck turned his head away, breaking eye contact with Vanessa, as the sound momentarily distracted his senses. Vanessa silently sighed, realizing this was going to be something she would have to bring to fruition.

Pulling tighter on his tie and using her other hand to direct his head to hers, Vanessa forced she and Chuck mere inches from each other. Breath on breath, their hearts beating fast, but beating in sync. The hairs on the back of Vanessa's neck and on her arms began to rise as her body tingled with anticipation.

The moment was upon her.

Vanessa pressed her lips to Chuck's, slow, soft, at first. She could taste the scotch on him, no longer forced to crave imaginary drinks. Her tongue began to gently part his mouth open wider as she pressed her body into his. Suddenly his hands were on her, no longer a meagre prop, but an active participate caressing and even groping at her form. Still, somehow, as the act became more passionate, more heatedly aggressive, it was filled with admiration, as if this act were the equivalent to a bouquet of flowers in their universe.

Chuck's hands moved to her hair, pulling her back as their bodies went towards the wall. Hands on hands and flesh and hair. Hands constantly moving as their lips were constantly moving, it felt to Vanessa as if there were no boundaries between them. Even her clothes felt like a formality. At that thought she felt her own hands latch onto Chuck's belt and begin to remove it from its leather loop.

Chuck, in an instant, pushed her hands aside and gently pushed her away. For a second Vanessa thought it was over, that she had crossed a line she never knew existed, but before she could compose herself he was on her once more, lips to lips. The implication was clear. They could kiss, maybe should kiss, but nothing more. Vanessa did not mind, she hadn't wanted that anyway, she had just gotten carried away. It had been so long.

Just as she began to relax in his arms, just as time seemed to slip into nothingness, the familiar sound of the elevator doors opening broke Chuck's concentration and Vanessa's bliss. Quickly they parted and stood awkwardly in the kitchen as Eric breezed past their right side, seemingly not even noticing them before heading up the stairs to his room.

Once he was out of sight Vanessa broke out into a huge smile, her face flush from kissing, her hair a tousled mess. Chuck watched her grin and chuckle to herself and he too could not help but smile. Then just as suddenly as he showed his teeth he turned away from her.

"I can't do this," he said.

"I've heard that before," Vanessa remarked, thinking for a moment that he was making some kind of joke.

"I'm being serious," he said in his most serious voice.

Vanessa looked shocked, dazed, but then she straightened out both her body and face and tried to act as if it was an expected response to kissing her. She tried to hide her disappointment and tackle the subject with logic. Logic with a beating heart was harder than she thought.

"This is what you said you wanted," she returned. "I asked, I asked you on the phone and this is what you said."

"That was before I knew…" his voice trailed off. The look on his face was one of doubt and dread. Vanessa could see he was pitying her, or at least that's what it appeared to be from her confused vantage point. He was feeling bad for having put her in this precarious position. While the sympathy was noble in some twisted way it was certainly not enough.

"Before you knew I would take you up on the offer," Vanessa finished, finally understanding. "You thought I wouldn't want you. That because you fled, because of your father, I wouldn't want this. You convinced yourself of that, maybe, like Dan says, that we don't belong together."

That remark made Chuck's eyebrows rise, but Vanessa thankfully did not notice.

"You thought this was the best. What was it Chuck? That you didn't deserve me or that I didn't deserve you?" she asked.

Chuck provided no answer.

"I may no be saving you from toppling over a building edge or cutting back your indulgent scotch habit, but you know I would take care of you and I think that scares you. I think you look at me and it scares you. Maybe you and Blair do deserve each other. And not because of the status or the social circles you mutually run in. And not because you're just so damn cute together. But because after all this time, all these flirtations and talks and trips and moments, you're still a sheltered little boy who wants his mommy. Gossip Girl said Blair was acting like a wife, but something tells me it was a little more maternal and maybe that's what you need."

Vanessa, without malice or anger, walked back toward the elevator. It was as if what she said was the most logically truth in the world, even if it was not. Somehow she was able to keep her calm, her composure. Somehow she was able to stare Chuck Bass down.

Once she was gone Chuck retrieved himself a glass of scotch, along with the bottle, and retreated to his room. Once inside he opened the drawer of his bedside table and pulled out Vanessa's scarf. He spent the night tossing and turning with a bottle by his side and the scarf wrapped around his hands and grazing gently against his face. Chuck spent the night trying to dream away the day.

New York City is full of so many interesting people, but even the most interesting can surprise you. Just what happened inside the walls of Chuck Bass's apartment is not entirely known. However, I can say the girl with a name was there and when she exited her lips were pink and plush. I may just be editorializing here or I may be preparing to say "I told you so." XOXO, Gossip Girl.