It should be obvious to everyone involved that your best friend and girlfriend are meant for each other if they find themselves doing everything possible to get over each other.
Chuck did not realise it until the night of the Waldorf party, the night Serena came back to town. He was sitting on the couch between Kati and Iz, assessing the talent in the room with the girls' help.
"How about the trophy wife in the Marc Jacobs?" Iz asked.
"Too commercial," Chuck replied. "I like a woman with a certain je ne sais quoi."
"Ooh, what about the hottie sipping the sex on the beach?" Kati giggled.
"She's about as common as her drink. And her teeth are too big."
"Wow, you may actually have run out of women in Manhattan to sleep with," Iz quipped. "You'll have to start flying them in from out of town."
"No, wait, I see one," Kati said excitedly. "Brunette in the corner. She's exactly your type."
Chuck turned to take in his potential prey. She is indeed beautiful. She is ivory-skinned, fragile-looking, with long, dark tresses and haunting brown eyes. She is Blair.
Not literally, of course, but in 'type' definitely. Suddenly Chuck felt irrationally angry with his companions. "Chuck Bass does not have a type," he murmured coolly. "I'm an equal opportunity player."
"Well, sure, you've had admirably diverse tastes," Iz gibed. "Eskimos, Australians, crazy red-heads, that guy from the Village..."
"Hey, at first I thought he was a female," Chuck interrupted.
"But you've always shown a proclivity for a certain type of girl," Iz carried on.
When Chuck continues to stare at her with bland disbelief, she spells it out for him. "You know, the chic brunette 'don't touch me' type," Iz finishes.
"Yeah, especially lately," Kati added thoughtfully. "There was that waitress at Butter last week, that haughty coat check girl at the white party...ooh, that bitch from Chapin..."
"Well, there's no need to continue the trend," Chuck cuts in acerbically. "Variety is the spice of life."
Years of practice at hiding his true emotions allow him to keep his voice level, his face detached. Inwardly though he is panic-stricken as his mind runs over all the faux-Blairs he has slept with in recent weeks.
Thank God, Kati and Iz are too shallow and self-involved to have made the connection, and have not guessed the reason behind his little penchant. But had Nate noticed? Had Blair? Since neither had been acting weird around him he could only presume they hadn't.
He felt sick inside, realising that he is so obsessed with Blair he had been subconsciously seeking out nightly substitutes with which to work out his frustrations. And the sad part is that it isn't helping. Not even a little.
With all that immersion therapy Chuck should be heartily sick of that Blair 'type', should be scouting the room for her exact opposite. But he now realised that the real reasons he had rejected the flirtatious looks of several women earlier was because their hair had been a shade lighter than Blair's, or their skin a shade darker...
It wasn't healthy.
It was even more pathetic that when Blair came around the corner, clinging to Nate's arm like a limpet a few minutes later, Chuck felt himself involuntarily smiling at her, like she had just made his entire day. While his attention was wholly absorbed by Blair, he covered for this by directing his comment at Nate, inviting him outside for some 'fresh air'.
Chuck knew part of the reason he made the offer was because he wanted to separate Nate from Blair, albeit temporarily. Yet somehow he managed to keep his smile in place as Nate refused, and Blair put in some flirtatious comment that indicated exactly why she was leading his best friend away.
Tonight was the night.
Blair had implied that she was getting ready to give it up to the golden boy the last time they had spoken.
Blair had made the decision to finally have sex with Nate the day she caught herself staring at the vee in Chuck's polo shirt, completely fascinated by the sight of the few dark chest hairs in view. If asked she would have said she preferred a guy with a smooth, muscled chest (like Nate's). There was something tantalising though about the idea of running her fingers across Chuck's chest.
Catching herself in the midst of this traitorous thought, Blair realised her hormones must have built up to dangerous levels. She had figured that kind of thing mostly happened to guys – had certainly never thought she would develop such an excess of hormones that it would lead her to these wild fantasies and involuntary physical responses – but obviously it had. And something would have to be done about it.
Sleeping with Nate would surely cure her of these strange new 'urges'. She would just have to find an opportunity to approach him.
The prospect made Blair nervous. It helped knowing that Nate was a virgin too, and therefore hopefully would not have too many expectations of her, but she was still terrified that she would do something wrong, or it would turn out that she was lousy in bed. In other situations, when confronted by her fear of failure, Blair would carefully plan a strategy to ensure her success.
But in this situation Blair had no one with whom to strategise. She could talk to Kati and Iz, who had plenty of sexual experience, but she could not appear weak in front of the minions. Allowing them to become too intimate would diminish their awe of her. If Serena had been around, and Blair had not been mad at her, Blair probably would have asked her advice. If she had managed to ignore her niggling awareness of Nate's crush on her best friend. Talking to her mother was completely out of the question. And she wasn't really comfortable bringing it up with Nate himself.
That really only left one person. Blair wasn't thrilled about talking about this with him either, but figured she could go about it in a kind of indirect way.
She had broached the topic the previous Sunday, when he had brought over coffee and croissants for their Audrey marathon. She had opted for Breakfast at Tiffanys, not only because it was her favourite, but because she figured it would give her plenty of opportunity to raise the subject of sex, given that the main character was a call girl.
She did not work up the courage to initiate the discussion until a good way into the movie, when Doc Golightly appeared on the screen.
"Ugh, can you imagine being married to an old man like that at thirteen," Blair shuddered.
"I can't imagine being married to him at any age, actually," Chuck drawled, eyes focused on the movie.
"But having to share a bed with him, especially her first time, it would be horrible, wouldn't it?" Blair prompted wildly, wondering how she was going to move the conversation round to what she really wanted to know.
"Oh, I don't know," Chuck drawled idly. "There are benefits to experience, you know Waldorf," he gave her his trademark leer. "Especially when it's your first time."
"Please tell me no one has ever fallen for that line," Blair wrinkled her nose in mock distaste.
Chuck laughed. "No comment. But it happens to be the truth. No one – girls I mean – enjoys their first time, but at least if the guy knows what he's doing it doesn't have to be a total train wreck."
Blair sat in stunned silence for a few minutes as Chuck returned to watching the movie. She thought it would be so romantic, her and Nate being each other's firsts, but now she was terrified. With neither one of them knowing what they were doing, were they doomed to be a train wreck? She wanted to enjoy her first time. She decided that she would just have to be an exception to Chuck's rule.
But to do that, she needed to know more about what it was she was actually supposed to do. What would turn Nate on. She had read the relevant literature in Cosmo and Cleo of course, but she wanted to hear it from a source she could absolutely trust.
As they watched Holly and Paul visit a strip club, Blair decided to make another stab at it.
"So do guys really like that?" Blair blurted out. "When girls strip I mean," she persisted when Chuck looked at her in surprised enquiry.
"Well, I don't think guys keep going to strip clubs for the quality of the food or the over-priced drinks," Chuck pronounced mockingly.
"But do they prefer watching a girl taking off her clothes to say, her appearing suddenly naked? Or given the choice would they prefer to take her clothes off themselves?"
(The issue of how to get to the naked stage had been bothering Blair quite a bit. She couldn't imagine stripping off before Nate, couldn't imagine being able to take off her clothes and look him in the eye at the same time. She had thought perhaps she could solve the problem by simply turning up to his room naked, but what if that was a turn-off? What if the whole slow erotic strip thing was somehow crucial to building the sexual tension?)
Chuck scrutinised Blair carefully. "Is there a purpose to this line of questioning Waldorf?"
Blair smiled sweetly. "I simply have an enquiring mind. You should know that by now Bass."
"But I'm sensing there may be something behind this particular inquiry." His eyes were still trained on her face with laser-like intensity.
"Just wanting to satisfy my curiosity. So are you going to answer my question, or not?"
Chuck studied Blair a moment. "You know I'm always ready to satisfy your curiosity, princess." It sounded distinctly like an invitation.
"Basically, if a guy gets to see a girl naked he doesn't much care how she gets that way. But there is something sexy about watching a girl undress herself for you, slowly revealing herself for your...pleasure. I think it has something to do with the self-confidence it shows," Chuck paused. "For instance, I like it if a girl maintains eye contact with me while she takes her clothes off."
Blair silently gulped at the way Chuck's voice lowered at this last revealing comment. She tried to convince herself that there hadn't been a part of tiny part of her brain that had picked up on this final remark as information to be carefully stored away.
"You know, for a price, I would be happy to let you practise on me," Chuck broke into her reverie about what it would be like to strip off for him, slowly removing her clothing one item at a time, maybe sashaying to some background music.
"What are you talking about?" Blair said non-intelligently.
"I'm guessing you're finally prepared to relinquish the pricey V-card to Nate, but are worried about disappointing him. So I'm graciously offering my services. I could train you up for the big event. Provided I got something in return of course. A favour, or an IOU of some kind." Chuck raised his eyebrow suggestively.
Even though he knew she'd never agree, Chuck allowed himself to indulge in this little fantasy. He would be rigorous in his teaching. And he knew exactly the kind of payment he would eventually exact.
There was a split second before Blair responded to his little scheme.
"Ugh, you're absolutely disgusting. I can't believe I let people know that we're friends," she pretended disdain, punching his arm for emphasis, although her cheeks were becoming warm and flushed at the thought of being Chuck's 'student'.
Chuck laughed and broke off a piece of pain au chocolate, popping some into her mouth and some into his. They lapsed into silence during the rest of the movie. But as Chuck was leaving, he gave her an unexpected quick kiss on the forehead. "You have nothing to worry about, Waldorf. You could never disappoint anyone, ever." Then he had hurriedly left.
Continuing nervousness meant Blair had not acted on her decision to sleep with Nate until she was finally propelled into action the night of the party by rumours of Serena's surprise return. She was determined to overcome the ghosts that haunted her relationship with Nate. Both of them. But it didn't quite work out.
Chuck had known exactly why Blair and Nate had disappeared into her room. It had made him feel sort of disconnected, somehow hollow. Then when Blair and Nate had quickly re-appeared to greet Serena, it was like he had once more come awake.
But he knew it was only temporary. Nate and Blair would eventually sleep together. It was inevitable. And even if Nate succumbed to his continuing doubts about the relationship and ended things with Blair, Chuck's fantasies about her would remain just that. Fantasies. Because Blair did not belong with a guy like him. And he didn't belong with anyone.
So he came up with a plan of his own. He had to quit having sex with assembly-line Blairs. Instead, he needed to have sex with someone who was her complete opposite. A blonde, maybe. It was the only way to prove to his body that one girl was just like any other.
A few nights later, Chuck was ruminating on the lack of success he had so far had with his plan as he sat in the bar of the Palace. His ruminations were somewhat impeded by the dangerous amount he had had to drink.
He had been hitting on non-Blair-like girls all night without luck. Perhaps the alcohol was hampering his charms. Perhaps they could sense the slight edge of desperation in his efforts. Or perhaps it was because his heart really wasn't in the chase, especially after he saw Blair come in, wearing his favourite shade of bright red lipstick.
It was a very distracting sight.
Chuck shook his head, trying to focus. He couldn't let himself dwell on those lips. It was pointless to fantasise about what he'd like them to do to him. And it made him feel sick to think about what they were going to be doing later.
He knew Nate was going to Blair's tonight. Part of him really wanted them to just get it over with, so maybe he could start getting on with his life. But in the meantime he was going to need a distraction. Preferably, one who was unmistakeably as unlike Blair as possible. Indulging his imagination had got him nowhere.
He didn't even have to like her very much. And on the whole he would prefer it if she did not like him. In his current state he had neither the mood nor the patience for gentleness. And any tenderness or affection would be too close a reminder of what he (in the most secret part of his soul) hoped he might find with Blair.
It was in the midst of these musings that Chuck's eyes lit upon Serena Van Der Woodsen. Blair's best friend. The girl she had met up with at the bar before her departure into the night to do the things that were churning up Chuck's insides. Blair's complete opposite.
With her wildly unstyled hair, 'natural' makeup and with the way she was attacking the vodka that had been set before her, Serena's unrestrained sex appeal was miles apart from Blair's cool, put-together beauty. Chuck knew that most guys, including his own best friend, preferred Serena's more obvious attractions.
But while Serena was undeniably sexy, Chuck had always felt that she was too light-hearted and bubbly to ever be the subject of a really deep, intense passion, the kind he believed Blair was capable of surrendering herself to.
He had told Nate on their way to school that Serena had looked effing hot at the Waldorf party. He had said it partly to try to draw his friend, although he also knew it to be true. But when he had said that she had the kind of perfection that needed to be violated, the truth was he had not been thinking about Serena at all.
It was not Serena that he wanted to violate.
But wouldn't it be a lovely touch of irony if he was to violate Nate's dream girl on the very same night that Nate slept with the only girl Chuck had ever regarded as the epitome of female perfection?
So he had approached her with his trademark Chuck Bass leer.
He had not meant to force her. Or maybe he had. He was drunk and desperate and bleak and maybe he just wanted her to hate him as much as he hated himself. After Serena had fought him off, he had downed a final triple shot of scotch and passed out.
He was so drunk he slept right through a dozen of Blair's calls later that night, when she was bewildered and sobbing and seeking comfort after finally finding out the truth from Nate and ending things with him.
If she had reached him, things might have been different.
But she didn't. Nate's parental deference and Blair's low self-worth conspired to ensure their reunion just a few hours later.
So the night of the Kiss on the Lips party Chuck was still on the prowl for a non-Blair.
The blonde freshman he had lured onto the roof was distinctly un-Blair. He could not remember her name. It had been something ordinary and prosaic, to match her pretty but ordinary face and her conventional, bland conversational skills. Actually, nothing much about her was making an impression on him, and that was about as un-Blair as he was going to get. Which was exactly what he wanted, of course.
Her brother had made a much stronger impression on him. Left it, in fact, on the side of his face.
He was really beginning to hate blondes.
It was poetic then that he should end the night with the brunette he had been trying to avoid.
"She better not show her face again," Blair announced to him, as he joined her in watching Serena's departure, signature scarf to his bloody nose. Blair felt the sentiment of her words even more strongly as she took in what Serena's latest hobby had done to Chuck's face.
"I'm kind of hoping she does," Chuck replied contemptuously. If she did, then Blair would act against her. And he would help.
Blair gave him one of her special smiles.
This was them at their best. This was what they were meant to be. Friends, plotting partners...and something more. Perhaps twin souls that shared the same peculiar intensities. So thought Nathaniel as he indifferently watched their exchange from the distance, swallowing down the rest of his beer.