A/N: Hi everyone, and welcome to my story, Shades of Grey. This is a little experimental piece of mine, which I was dying to write after the last episode of Gossip girl. This story will be about 20 chapters, and takes place after 2x08 Pret-a-poor-Jenny. I haven't decided who the end couple is yet, Blair/Dan or Blair/Chuck.


Chapter one: Personality clash

Blair pushed the straw around her cold drink while staring at her crimson nails in boredom. Starbucks was becoming increasingly dull by the minute, and Blair kept replaying the events of last night in her head. Normally, she would have her best friend, Serena with her, and they would be sipping their usual iced mocha's with whipped cream, but Serena was spending time with Aaron. Therefore, Blair buried her head in a magazine, while pondering over her non-existent relationship with Chuck and lightly sipping her beverage. She had to wonder, if she told Chuck she loved him, would they be together? After all, Chuck didn't entirely seem convinced when he gave that speech about their doomed relationship. Blair shouldn't have listened to Humphrey's stupid advice in the first place; she didn't need Brooklyn trash teaching her about love.

Who would want to see Chuck and Blair holding hands and going to the movies anyway? Blair thought moodily, in response to her vivid memory of Chuck mocking the traditional actions of couples.

Rising from her chair, Blair swiveled around blindly and collided with a solid figure. In a flash, the contents of her latte drenched her designer coat, also managing to dampen the majority of her hair.

"Great," Blair muttered under her breathe. Just her luck. Wiping the mess up with napkins, she locked eyes with the culprit, only to find Dan Humphrey lying on the floor, wincing in pain. Trying to regain her balance, Blair glared daggers at him, while thinking of a million different ways in which she could ruin his life. Out of all people, it had to be the person that ruined what should have been the most romantic night of her life. Despite her fury towards him, Blair couldn't help but wonder what her best friend was thinking when she dated him. His hair was disorderly, and his clothing was so casual and unkempt that it made Blair want to scream.

"Oh, god, sorry Blair… I didn't mean-" Glowering at the person before her, Blair grabbed Dan's hair, pleased to see him gasp in surprise. Dragging him outside, Blair wasn't aware of onlookers pulling out their phones, most likely to inform gossip girl of Blair's sudden outburst.

"Ok, cabbage patch, here's the thing," Blair spoke venomously. "I was planning social suicide, but then I remembered you have no friends. Pull another stunt like that again, and I will ruin you." Dan stood there quietly, shifting his weight from one leg to the other, occasionally casting her mocking glances. Once she had finished her rant, Dan decided to speak.

"Um, Waldorf, don't you think you're over reacting?" Dan shrugged nonchalantly.

Blair rolled her eyes in disdain. "You know cabbage patch, for someone that's meant to be smart, you sure are dumb." Noticing the confusion in his eyes, Blair decided to elaborate. "If it weren't for you, Chuck and I would be together."

Dan just stood there, comprehension evident in his features. After all, what she was saying was true, but he had good reason for his actions. Dan tried to think of a response to her remark. However, it didn't matter, because Blair shook her head, cutting him off from anything he had to say. Dan looked at her in disbelief. Could he see tears in her eyes?

"You know what Humphrey? Just forget it. I'll send you the dry cleaning bill." With those final words, she stormed off.


Any doubt that Dan had in his mind about Blair's love for Chuck was gone. Who was he to judge the complicated relationships of the upper-east side anyway? Maybe it was the way she looked at him helplessly, that made Dan feel extremely guilty. However, the thought of her being melodramatic had also crossed his mind. Sighing in defeat, he pulled out his phone, and punched the digits of Serena's number in.

"Hello," a cheery female voice answered.

"Hey, Serena its Dan…" The palms of Dan's hands were beginning to perspire slightly, as he contemplated what to say next. After a few seconds, he came to the conclusion that it was best to be blunt."I want to get back on Blair's good side."

He winced as the words left his mouth. Maybe a little too blunt. Why should he have to make things up to a girl who thought he was a piece of dirt on her shoe? No… he wanted to feel less guilty about upsetting her. That was it? Right? Besides, since when was he ever on Blair's good side?

"Ok," Serena replied in a surprise. "But Dan, I thought you said the other night that you didn't care about Blair, and you were only giving her advice to help our friendship."

"I know, that's true, but no one deserves to have coffee spilt on them the day after a confrontation with Chuck," Dan paused briefly, preparing for the storm that was about to come. "Actually I'm not exactly sorry for the bad advice..."

"Dan!" Ok, Maybe the wrong words, Dan thought wearily. He didn't react well under pressure, but it was true. Chuck and Blair had toyed with his best friend, and Vanessa even declared that Chuck was the more human of the two. "Firstly, she was wearing her favorite Versace coat today," Serena practically groaned into the phone. "And secondly, did Vanessa tell you what she did for Blair to get that angry with her?

"No," Dan said frowning. "What could Vanessa possibly do to get that sort of treatment from Chuck and Blair?"

"I'll let you talk about that with her when you go over and apologize," Serena answered instantly, as if it were the simplest thing in the world. "Look, Dan, B isn't that bad. If she sees you're making an effort, she'll be a lot nicer."

Dan's brain was working overtime. He sincerely doubted that Blair could even smile at him, let alone exchange pleasantries with 'Brooklyn trash'."Ok, I'll go over and apologize, but don't expect us to be friends," Dan affirmed. "And I thought you should know that I'm only doing this to put an end to my inner turmoil."

"Fine, but I think you'll be surprised at B. Tell me how it goes," Serena responded in a hurry. "Sorry Dan, Aaron's finally picked out a movie. Got to go."

Dan sighed in relief that the conversation ended, just before he could let his jealous ex-boyfriend side take over. Serena may have let go of him, but Dan knew it would be ages before he could let Serena go completely. Turning his i-pod on full blast, Dan tried to forget that he was traveling an extra half hour for some girl who hadn't even called him by his first name. He had been to her place, once, when they were plotting against Georgina.

At least I know where she lives, Dan reflected vaguely. Etched into his memory, was a large building worth enough money to feed his family for two years. Yep, he wouldn't get lost. Slightly rolling his eyes, Dan exited the train at the next stop, and hopped onto another platform, waiting for the transportation that would take him back towards the Upper East Side.

"To end the inner turmoil Humphrey," he kept repeating to himself when he started questioning his intentions of apologizing to Blair.


Blair strolled down random isles, eagerly awaiting a mystery outfit that would hopefully put and end to her miserable day. Mentally, she made a note to never visit the tedious boutique laid before her; the clothing was poorly sewn, and the fashion was seasons behind. Nothing seemed to be going right for Blair today. Turning on her heel, she exited the shop and retreated back to the limo that was parked outside waiting for her.

The sight of her coffee stained designer coat ruined the normally satisfying experience of relaxing into the limo's comfy leather seats. Blair frowned at the earlier occurrence today, when Humphrey had nearly reduced her to tears. Her accusation towards him, concerning Chuck may have been a tad unreasonable, but Blair wasn't one to apologize. Especially to some judgmental Brooklyn boy, whose best friend was a cabbage patch doll. Now, strangling Humphrey had to be added to her to-do list, along with discussing last night with Chuck, and getting into Yale.

Blair suddenly felt the limo come to a halt, therefore concluding that she was at her destination. Home. Gathering her Gucci bag, along with her coat, Blair managed to gracefully depart her means of transportation and sauntered towards her house. "Dorota," she called out bossily, after unlocking their giant wooden door. "I need you to run an errand for me-" her words were cut short when a familiar face came into view.

"Cabbage Patch?" Blair questioned, so surprised that she failed to appear angry at the person in front of her. Suddenly realizing her mistake, she hastily crossed her arms, and raised an eyebrow in distain. "What are you doing here?"

Dan tried carefully to choose his words, as she looked at him in anticipation. "Um, your maid let me in," he stated lamely. "I'm here… to apologize for your coat, I'll um… take it with me to the dry cleaners."

Blair rolled her eyes at his tendency of rambling. "My three-hundred dollar Versace coat is not going anywhere near Brooklyn. I'm scared of what you peasants might do to it." Blair knew she was treating him worse than she ever had, but she didn't care; he deserved every word. She could tell that he was affronted by the look on his face.

"I'd rather be a peasant as opposed to a rich upper-class snob, who contributes nothing and takes pleasure in ruining people's lives," Dan growled in frustration, as he already started towards the door. It amazed him that before last night, he actually thought Blair could be ok. "Oh and by the way, I don't pity you and your situation with Chuck. Not after what you did to Vanessa."

Walking towards the door, Dan was astonished to hear a small laugh coming from behind him. "Vanessa deserved what she got," Blair spoke simply, as Dan turned around to face her again. "She blackmailed me with that picture of Marcus and the Duchess."

Dan's eyebrows knitted in confusion. "But, Vanessa-"

"She's no an angel Cabbage patch, contrary to you deluded belief," Blair smirked slyly, and put her game face into play. "I know that you deliberately told me what you did to ruin what could have been between me and Chuck." Blair, much to her own surprise, was slightly disappointed when she saw the truth staring back at her. The fact that he was from Brooklyn made Blair trust him slightly more than she would with any of the girls in her posse. It wasn't like he had the ability to spread gossip, which was a small comfort to Blair. Humphrey was impossible to figure out. Not that she'd want to.

"Why would Serena tell you that?" Dan inquired with confusion as to why Serena would want to cause a dispute.

"Serena's my best friend. Remember? You're just the ex-boyfriend." Blair snidely commented.

"I'm sorry for any damage I caused Waldorf." Dan couldn't believe those words had left his mouth, but he found himself apologizing to Blair for the second time that day. "I'm sure Chuck will come to his senses," he tried to reassure her.

Blair stared at him blankly. Being infuriated with him was proving to be difficult, when he seemed so calm and sincere. Knowing deep down that the outcome for her and Chuck might have been the same with or without Humphreys words made Blair feel even guiltier. Just as he was about to leave, Blair gave into her conscience. "Humphrey." Watching a small smile outline her lips, Dan observed her change in attitude. "Don't worry about the coat. I'm sure Dorota can take care of it."

Taking into account the two factors of Blair nearly smiling, and letting him off the hook with her coat, Dan knew that his work here was finished. Awkwardly leaving the Waldorf residence with a slightly new perspective on a certain person, he felt a weight lift from his chest.


A/N: Coming soon... Blair/Chuck interaction and Gossip girl posts :). Good? Bad? Should I continue?