Hey! So this is a new series of one-shots I'm going to do in the viewpoints of various characters on the NJBC. This is just to get my creativeness flowing! Timeline is everything until the beginning of season three. Disclaimer: I don't own Gossip Girl. Get it through your head!
Dan Humphrey, the "ultimate outsider", had a hard time understanding the Non-Judgmental Breakfast Club. At first, they seemed nothing more like caricatures out of a novel. Blair Waldorf was the bitchy, controlling girl, trying to make her feel better about herself by putting others down. She was the kind of girl who didn't care if she stepped on people to get what she wanted. She hid her ruthlessness behind cute clothes and excellent grades. Blair was, simply put, a monster.
If Blair was a monster, Chuck was the devil himself. He had no soul, no heart, as far as Dan could tell. He was the ultimate playboy, his usual routine consisting of booze, girls, and drugs. Chuck had money and knew it. He, like Blair, would use whatever means necessary to get what he wanted. Chuck was one scary bastard, and yet Dan still found him to be fascinating simply because of his demeanor. Nothing fazed Chuck, nothing bothered him. Chuck was like ice.
Dan noticed nothing remarkable about Nate at first impression. He was just your average, some-what dopey jock with a hot bitchy girlfriend. Nate was a relaxed, go-with-the-flow kind of guy. He let other people run things instead of handling them himself. Nate was, in Dan's opinion, a guy who just didn't know what he wanted. Nate didn't know if he wanted to be with Blair or go to law school or be a jock. He just didn't know.
And then there was Serena. Dan had been in love with Serena ever since she said hi to him at a party in the ninth grade. She was beautiful and graceful, reminding him of a Greek goddess. Serena was bubbly and fun, and being around her just made you shine. He had heard the rumors about her, heard all the things she had supposedly down, but figured that no girl this sweet could possibly ever do anything that bad.
Of course, the longer he was in their world, the more he realized not all of his assumptions were true. The caricatures he had imagined early started to gain flesh. Blair was a bitch sometimes, yes, but she was also a good friend. Dan watched Serena and Blair together, watched how Blair always seemed to have Serena's back. Even when the two were fighting, he had noticed Blair would never let anyone bad-mouth Serena. He remembered the look of fierce protectiveness Blair had on her face the day he came to her house to confront Serena.
Likewise, Chuck Bass also had a human side. Dan hated Chuck Bass for trying to take advantage of his sister, but he had to admit the guy did have a heart. Chuck covered for Serena when Georgina came around and almost seemed to have a brotherly protectiveness of her, one that only intensified when Lily and Bart got married. It was obvious Chuck loved Blair, or at least had strong feelings for her. Dan could tell by his eyes. Rhett and Scarlett all over again, he mused to himself.
Nate, too, had more depth than Dan expected. He had forgotten that Serena and Nate had a history. He knew they had slept together but had chalked it up to the reason Serena had slept with so many guys before: too many drinks. It soon became clear, however, that there was something between the two. In the course of his and Serena's relationship, Dan knew that his girlfriend's connection with Nate had been strained at best, but he also knew that if Serena had called Nate needing him, he would've come. Nate loved Serena, and that scared the blonde for some reason he couldn't figure out. Why hadn't Serena been afraid to love him?
Of course, Dan had figured this out months after their first breakup. Serena had loved him with the reassurance that the relationship would fizzle out somehow eventually. Her relationship with him had been the same as her flings with so many other guys. They had been temporary. Nate was a constant for Serena. He had been there from the start, and she wanted him until the end. She viewed loving Nate as too risky.
Seeing the real Serena definitely broke all the illusions he'd always had about her. The real Serena wasn't some perfect angel on pedestal. She was simply a girl, a beautiful girl who had already made enough mistakes to last a lifetime. It was hard for Dan to imagine the energy she put into their relationship, the way she had to push out all the bad parts of herself to fit his image of her. It gives Dan hope, hope that their relationship was actually worth something to her, and it also made him sad, sad that she couldn't reveal her true self to him.
Dan realized that, in the end, he was just the "ultimate outsider". He'd never belong in the Upper East Side, in the tightly knit world of Nate, Serena, Blair, and Chuck. Fortunately, he did have fascinating characters to study.