So don't ask me how to get started, it's all uncharted.
– "Uncharted" by Sara Bareilles

"Taking someone down" was usually not in Dan Humphrey's vocabulary. But when it seemed to come to Juliet Sharp? It seemed almost second nature to him.

But what surprised Dan the most was that he helped Blair, and he enjoyed it.

The fact that he enjoyed it made him recoil in horror (if only because he couldn't believe that he had actually come around to liking the thought of 'taking someone down' when he used to be entirely opposed to the idea) was nothing new. He had been involved in plots to take down Georgina Sparks, several times over, as well as other plots including Carter Baizen, and Serena's dad, just to name a few.

It was the fact that he had come to enjoy spending time with the petite brunette, and he didn't even mind her clucking her tongue in disgust as she looked at the outfit that he wore.

They may not have been classmates at NYU any longer, but it didn't mean that they couldn't spend time together, right?

It had been an awkward few weeks after the take down: Dan was at Columbia to meet up with Nate and Blair was waiting for Serena to come and see her. They both bumped into each other at the same place and while it was somewhat awkward at the start, her fake smile said it all. She was being civil, and that was all she could have expected from her.

That was when he suggested the unthinkable – going out for a coffee. He didn't know why he did it, or why he even thought of it. But he was friends with Nate, and Nate was friends with Serena and Blair (perhaps more Blair than Serena considering their history) and whilst Dan had a past with Serena, they were most certainly on the friends page now.

He actually wanted a clean slate with her, a fresh start. First impressions were everything, and he would have imagined that their first encounter at Thanksgiving several years ago wasn't all that fantastic (granted if she even remembered that time).

But luckily for him, she agreed. Begrudgingly.

And that was when Serena flounced her way towards the pair with a somewhat high pitched squeal, hugging Dan and asking him what he was doing on campus; his conversation with Blair forgotten.


Walking down the street with a venti sized cup of Starbucks was something that Dan did frequently.

Doing this with Blair Waldorf? Something that only happened recently.

After their first coffee 'date' (if you could have put it that way), he had managed to learn more than he would have wanted to. No, they weren't dating, and he didn't even remotely think about wanting her in that way. But he could make the link between the coffee that she took with her personality.

It was then that he started buying coffee for her before their regular meets with their respective friends at Columbia.

Serena started getting suspicious that he only bought coffee for the brunette and not herself. He then started shelling out more money to buy a cup for the blonde as well.

But as Dan was sipping his coffee, he heard Blair squeal about something, causing her to tug on his jacket and pull him into a store.

Somewhat stumbling, he furrowed his brows and looked around. Clearly, this was something that Serena should be doing. But considering the company she had, he was going to have to step in for her.

Clenching his jaw, he looked at the dresses and other various clothing items that were on offer, trying not to look too surprised at the prices. He may have looked like he shopped at an op shop, but at least he didn't have to break his bank every time something went out of fashion.

"Humphrey!"

Looking up quickly, he saw the brunette gesturing for him to come over to look at something. His venti dangling by his fingertips, he wandered over to Blair, seeing her pick up a dress off the rack and looking at it.

"What do you think of this?" she asked quietly, her delicate fingertips stroking the garment.

"I think it's ridiculously overpriced for the amount of material that you're getting," Dan muttered quietly, taking a breath. "I mean, you should be getting a six foot train with that,"

Blair slapped his chest. "No I'm serious, Humphrey. I know you don't have the greatest taste in fashion," she paused, turning to look at him with a knowing smile. "But you know, there's that gala coming up. I need a new dress,"

"But there's always going to be an event to buy a new dress. Why do you need it for this particular one?"

She slapped his chest once more. "Yes or no Humphrey. That's all I need,"

He smiled, turning his attention to the dress. Tilting his head slightly, he watched as the brunette picked it up off the rack and holding it up to her body.

"It looks different on a body," was all he said.

She laughed it off before putting it back on the rack and leading him out of the store, leaving him to continue sipping on his venti.


Dan had gotten used to these gala events. He had about five designer suits in his closet and a couple of good tuxedoes, all thanks to Lily. His life had drastically changed ever since Rufus and Lily got back together again, and what was Dan to say about his father's happiness?

He had been making small talk with another guest for the past five minutes, hoping that the announcement that was supposed to happen would actually happen soon. He was getting restless, and he would have preferred to get back to Brooklyn on time. He still had two papers to write and one was due in two days – and he hadn't started on that one.

He was a college student, it happened all the time.

But his attention was diverted when he felt a presence right next to him. With a silent huff, he knew who was standing beside him. Excusing himself politely from his conversation, Dan stuffed his hands into his pockets before turning to look at her.

She bought the dress from the other day.

And she looked exquisite.

"So I see you bought the dress," he commented with a light smile.

"With no help from you, Humphrey," the brunette said, elbowing him in the ribs. Dan cleared his throat.

"I had to bring Serena in the next day and she approved of it. You didn't even suggest me to try it on,"

"If you were to try it on, I wouldn't know what to say. As you said before, I don't have the greatest taste in fashion,"

Blair gave him another one of her infamous fake smiles before she walked away from him, spotting Serena off in the distance. Inhaling deeply, Dan blinked slowly with his jaw clenched, watching the brunette move gracefully through the crowd.

He should have told her to try on the dress.

Then maybe he wouldn't have felt that breathless.


It had become their Friday morning tradition: Dan meeting up with Blair on campus before she'd lead him off to the nearest Starbucks so they could get their caffeine fix, before wandering down the streets lined of clothing shops.

It wasn't Dan's cup of tea, but he had somehow gotten her to read his stories and give him critique. The coffee and the walks on Friday mornings was his payment to her. After all, she didn't have to read his work, but he was glad that she was.

Stopping outside the same store a few weeks ago, Blair pulled him inside once more, his venti being held in place by his pinkie and his thumb. He wasn't all that sure whether if he was in the mood to be inside a clothing store right now, but he knew that this was how he paid her back.

She picked up another dress off a rack, and this time, without asking him about it, got herself whisked away into a changing room.

In fact, Dan had to ask one of the assistants where Blair had gone before he heard a voice behind him.

"Here, Humphrey. Maybe you can give me an opinion considering now it's on my body,"

Rolling his eyes slightly with a light smile, he eventually turned to look at Blair, about to retort when he saw the dress that she picked out and how she looked. Needless to say, what he wanted to say initially had definitely changed – for the better.

He was speechless, and for one of the first times, when he should have had something to say, he had nothing to say.

"What's the matter Cabbage Patch? Finally rendered speechless?" the brunette asked, the ends of her lips curling up into a wicked smile.

He cleared his throat and simply shook his head. "No, of course not. I just needed to think of a few words to describe the dress you're wearing," he muttered. His arm moving across his body, he raised his finger to his lips, tapping it several times over as he started to make a circle around Blair, the brunette staying perfectly still for him.

"This is going to be for Tuesday night, right?"

The brunette rolled her eyes, turning to face him. "The very question in itself is redundant, Humphrey,"

Moving his head from side to side, Dan finally nodded and lowered his arms.

"I like it," he stated, his eyes widening slightly in the process. "I mean, I like it. But you should really get Serena in. See what a girl with fashion sense actually says about it,"

Blair smiled and nodded, her hands gently smoothing out the dress. "Of course, Humphrey. I wouldn't just buy a dress just because you told me I looked good in it. I'm not trying to impress you here,"

Scoffing gently, she turned back towards the direction of the change rooms, pulling the heavy curtain across with such grace.

Dan clenched his jaw, and for the first time, he sipped his venti in the store.

Maybe he wished that she was trying to impress him.


Months passed and Dan caught himself looking at Blair more often. He wished he didn't know why he did, but that probably would have ruined his buzz.

He had helped Blair through several dress fittings and seen her waltz through countless events and galas with the exact dress that he had told her to get. He had even helped her zip up on several occasions.

Their relationship was nothing more than just a friendship, and she had always been adamant about that.

But why did he always feel like he wanted more from it?


It was that time of the day again; venti in hand, Dan was sipping it quietly before he found himself being pulled into the same store. Dan didn't even blink now. It was clear that this was one of Blair's favourite boutique along the street, and he wasn't going to deny her going inside.

But this time, he kept up with her, entering close behind her as she walked through the doors. Looking around, he eventually spotted something that could have looked passable by his friend's standards.

Picking it off the rack, he held it high (so it didn't trail along the floor) before calling out to the brunette.

"Blair,"

She turned around with an arched brow, a critical look on her face.

Admittedly, he had suggested a few dresses for her in the past and she had just waved them off with her hand. But this time, she stared at it intently, her eyes moving up and down the garment.

Did he finally pick something that she might have liked?

"Acceptable, Humphrey," she said approvingly with a nod and a smile. "Maybe there's hope for you yet,"

"So does that mean you like it?"

She shrugged lightly. "I might,"

Dan felt an odd swelling in his chest, and he might have puffed it out somewhat. Blair laughed.

"I give you one compliment, and you're sticking out your chest at me. Classy, Humphrey," she muttered quietly, shaking her head slightly.

He smiled and shrugged slowly, turning a light shade of pink. God, what the hell was wrong with him?


It had been a year since the first time that they sat in the café that they went to every Thursday afternoon. For the past three months, Dan had been wrangling with an inner demon. He wasn't the greatest at reading signs, or reading women for that matter, but he couldn't help but fight the feeling that maybe Blair had some feelings for him. No matter how inkling the feeling might have been, he couldn't ignore it.

Over the past year, Dan himself had changed. He now didn't mind the weekly shopping walks that he went with Blair. In fact, he owed Blair a lot of credit when it came to his choice in clothes. It also helped that she decided that she would dedicate one day every six weeks to looking for clothes for him. In the beginning, it was tedious. Now, it seemed natural.

Wearing the shirt that she bought for him just two weeks ago, Dan sipped on his venti, instinctively following Blair into her favourite boutique. They had become regular customers; all of the assistants knew them by their first names, and they didn't mind him sipping his coffee in the store.

Making a bee-line to a rack of dresses, he casually fingered through it, wondering if anything would catch her eye. Yes, he started shopping and looking at things to impress her. Blair had definitely noticed the change in him, but Serena was much more surprised.

Of course, the blonde had deduced that he had feelings for her best friend.

And she gave him her blessing.

That is, if they were to ever work out.

Eventually lifting his gaze, he spotted a dress on a mannequin, instantly knowing that it was the one for Blair.

"Blair,"

"Which one now Humphrey?" was all she asked, knowing that he had found a dress for her.

Dan watched as she turned around to look at him, her eyes lighting up at the dress that he was gesturing at. He had picked the winner, he could tell. Her mouth was barely agape, trying not to let on that he had finally impressed her, but he knew that he had.

She promptly closed her mouth, giving him a knowing smile. "Well Humphrey, it would appear that the student has become the teacher,"

"Well, why don't you try it on?" he questioned, watching her take a few steps closer to the garment.

"Dan, I couldn't," she said softly, her fingers moving gracefully across it. "Even if I wanted to,"

She had just called him by his first name for the first time. Ever.

He couldn't help but feel a sense of accomplishment.

"Oh, come on, what's the worst that could happen?"

He received no answer, which meant that there was nothing wrong with trying it on. The fact was she didn't want to. Perhaps it was just a dress that Blair had always wanted, but had the dream that she could have never owned. He didn't know what went through that brunette's head most of the time, so he didn't push it.

"Look, there are even some matching shoes to go with it," Dan piped up once more, pointing at the shoes that were placed down by the mannequin's feet.

She scoffed.

"It's going to take a lot more than a dress and a pair of heels to make me try it on for you, Humphers,"

He gave her a sly smile, furrowing his brows slightly. "Well then what would it take for you to try them on?"

Walking away from the garment and out of the store, he followed her dutifully until she stopped right in front of him, causing him to stop abruptly.

"It'll take just as much as it'll take me to jump into bed with you,"

She turned on her heels and started to walk down the street once more, Dan blinking several times.

"Challenge accepted,"


Dan didn't know how he did it, but he boiled it down to the fact that he had some sort of relationship with the store assistants.

A bit of flirting never hurt anybody, right?

Clearly not.

Dan had walked into the boutique with an odd confidence that he was going to get the dress and shoes with ease. And as he walked out, all he could think of was "wow, that was easier than I thought."

He took in a deep breath and puffed his chest out, giving everyone that walked past him a smile before he made his way to the bus stop; the dress bag hung carefully over his arm and the shoe box securely tucked underneath his other arm.

She was going to go into conniptions.


Dan had gotten a text on his cell for Serena to come to Blair's place, and he promptly went. Spotting the blonde as soon as he stepped out of the elevator, she just looked at him with a knowing smile.

"You did it, didn't you?"

Dan gave her a slight smile, tilting his head to the side slightly. "Did what?"

"You got that dress for her. With the shoes,"

He furrowed his brows to further try and confuse the blonde (which sometimes did work, but evidently this was not the case today).

"I don't know what you're talking about, Serena,"

The blonde laughed. "Come on Dan! Don't play coy with me, I know all of your tricks," she said with a grin. "You don't think I don't remember about the time you brought a Christmas tree into our hotel room,"

Dan smiled. Yes, that plan was ingenious. He did have to give Jenny some credit for helping him… as well as Lily.

"How did you even get it? That dress is, really expensive," the blonde said quietly, her eyes widening slightly as she emphasised the word 'really'.

"Look, Blair and I have been going there for a year, once a week. The girls there know me,"

"You're trying to say that you got the dress of her dreams because of the fact that you managed to swoon a couple of women down at a boutique?"

Serena was on the ball. But then again, when it came to matters involving Blair, she always looked out for her best friend.

"I-" Dan started, moving his hand in a circular motion "I managed to get it through several payments over a specific period of time, which, is undisclosed, thank you very much,"

Serena laughed lightly once more. "Oh my god Dan. Please tell me you did not rent that dress for her,"

"No! No no no no no," Dan repeated, feeling slightly offended. "I did not rent the dress. Please, no, I have more tact than that, v d W," he smirked slightly.

"I bought the dress. And the shoes. I'm just paying the store in instalments, that's all,"

She smiled and nodded, biting her bottom lip gently before leaning in and kissing Dan on the cheek.

"For your information, if this is your way of getting Blair's attention, it might be working,"

Dan smiled before Serena patted him on the shoulder, gesturing for him to go upstairs.

"She's waiting for you. The last time I checked, she was hyperventilating. You should make sure she hasn't passed out yet,"


Dan knocked on the door, hearing a heavy breathing sound on the other side. She really was hyperventilating. Pushing the door open, he peered inside, seeing Blair simply sitting at the edge of her bed, staring at where he had hung up the dress for her earlier.

"Do you like it?" he asked quietly, the door clicking shut behind him as the brunette simply stared at him.

"Humphrey, how did you even manage to get this?"

She didn't even sound grateful.

"Do you like it?"

"Do you know how much this thing costs?"

"Do you like it?"

"Humphrey!" she exclaimed, finally standing up and stamping her foot.

"Do you like it?"

She sighed, giving him a single nod. "I love it," she whispered quietly.

He gave her a satisfied smile, slipping his hands into his pockets. "I knew you would,"

Blair moved closer to him, her hands resting against his chest as she looked deep into his eyes.

"But why did you do it Dan?"

She said his name again, twice in two days. Dan liked where this was going.

"Because I knew you liked it, except you didn't want to try it on. Which really confus-" he was cut off by Blair, placing a delicate finger against his lips.

"How did you even know? How did you even- How could you afford it?"

Dan gave her a knowing smile before simply shrugging, his hands eventually finding their way to her hips. This was the first time that he had touched her this intimately while they were alone. Yes, he had seen her bare shoulders when he had zipped her up in a dress, but this was different. She didn't need his help and this wasn't because they were about to go to an event. He did this because he wanted to.

"You don't have to worry about that, Blair. The dress, and the shoes, they're yours to keep," he murmured.

As they held each other's gaze, Dan was quite sure that she saw something in his eyes that she had probably never seen before – genuine generosity.

Dan knew that everything on the Upper East Side came with a catch, no matter how good the deal was. And at the moment, Blair was probably trying to find out what the catch was. He didn't blame her.

"There's no catch, just in case if you were wondering," he stated firmly, tilting his head down slightly.

Her lips parted slightly to speak, pausing for a moment before continuing. "How is that possible that they would just hand you a dress like that?"

"Well, they didn't just hand it to me, like you said," he said with a light laugh.

"Then how di-"

He interrupted her again. "Blair. Shut up. Go try it on,"

The brunette smiled and leaned up on her tiptoes, kissing his cheek softly before rubbing the other cheek.

"Thank you, Humphrey," she said with a quiet voice, a smile in her eyes.

Moving out from his grasp, she rushed past Dan and opened her bedroom door, squealing at Serena to come upstairs. As soon as the blonde bounded up the stairs and back into the room, Dan quietly let himself out to let the girls bond. As soon as he shut the door, he could hear the squeals of excitement from both the girls, a smile creeping upon his lips as he made his way out of the brownstone.


It had been a few months after Dan had bought the dress for Blair. He had been paying the boutique every time went into the store with his friend, and he had never looked at another dress for her again. The dress that he managed to get for her would have been so easy for her to buy. But for Dan, it would take a while to repay. His stepmother may have been Lily van der Woodsen, but he wasn't going to be taking money from her to pay off a dress that wasn't even for her.

Dan had given up his weekly venti and a few of his other life pleasures to pay for the dress. Blair probably never saw how much he actually cared for her, how much he wanted to see her happy. But he would have moved the entire earth for her just to see her smile.

He had always caught himself looking at her out of the corner of his eye as they were sitting quietly together, reading their books. Sometimes he noticed the way she furrowed her brows gently, the creases in her forehead showing for only a moment. He had never told her that he always found that somewhat cute, but just told her that she would get wrinkles earlier than she should. And then when he mentioned that, she'd give him a playful grin before rubbing her forehead and continuing to read.

But the more that he had been fighting his feelings for her, the more that he thought that she had been doing the same. Over the past sixteen months together, the amount of time that they had spent together had grown exponentially. None of them could explain in detail as to why they found each other as company, but Dan wasn't one to complain. He found Blair's company somewhat comforting and brutally honest. They rarely agreed on anything, but that was what made their relationship so honest. There was no façade – that was who they were, and there was nothing in the way of that.

Dan was seated on the couch when he heard a knock at the door, making a mental note of where he was in his book. Closing it and tossing it onto the coffee table, he made his short distance over to the heavy door, pulling it open to see Blair standing there. He gave her a slightly incredulous look.

"Blair. This must at least be the fourth time you've been in Brooklyn," he said with a slight smirk.

"Shut it Humphrey, I'm here on van der Woodsen business," the brunette sighed. Pulling her gloves off her hands one at a time, she stepped inside and looked around the loft.

"Serena said she left some book here or something. I'm meeting her for dinner tonight and she's caught up on the other side of town. And of course, I just had to open my mouth and say that I was coming down to see you later,"

Dan smiled and rolled his eyes slightly, making his way into his room and leaving Blair to her own devices in the loft. She had already scrutinised every single corner of the loft, made a list of the appropriate adjustments that he had to make to make sure that the place was still feasible to live in – he kept the list in his desk drawer.

Fetching the book, Dan came out to see Blair looking at the book that he was currently reading.

"Interesting choice, Humphrey," she muttered quietly, the corners of her lips turning up slightly.

"Always something good to take my mind off what's happening out in the real world," Dan muttered quietly, walking up to her and handing the book to Blair. "Serena wouldn't get anywhere with this book,"

Blair looked at it and laughed slightly, nodding and tucking it underneath her arm.

"You know S. She can only get away with so much," Blair said, looking up at Dan with a smile.

He nodded in response, taking a step closer to take his book back from her. And in that moment, when he leaned in, she did as well.

There was a moment, if only for a mere second, where he hesitated. He paused, wondering why they were both leaning in, and before he knew it, their hands were touching on his book, their noses almost about to brush up against each other.

He had tried to fight every single hormonal instinct in his body up until this very moment. This time, he tried his hardest, but he failed.

Dan shifted his head down slightly before eventually pushing his lips up against Blair's in a firm kiss.

She had been caught off-guard, just as much as he wasn't expecting to kiss her. But she didn't recoil in horror, neither did she push him off either. There was the initial gasp against his lips, but he felt her ease into the kiss.

And just as it had started, it had ended; Blair pulling away from Dan, their lips parting making somewhat of a 'smacking' sound. He looked into her eyes, trying to look for some sort of sign from her, but all he got was her fingers flying to her lips and giving him a wide eyed look.

It almost looked like it had been a mistake on her part.

"I'm sorry Dan. S really needs this book, I should go,"

And with that, she scuttled out of the loft and slammed the door shut, leaving Dan with his book dangling in his fingers.

And he was sure in that moment that his heart broke.


Dan had a bad track record of confessing his feelings to girls that he liked. The first time he told Serena that he loved her was met with a reaction that he wouldn't have liked, the first time that he told Vanessa that he loved her led to her moving away, and when he told her the second time, they were in the hospital and she didn't want to talk about it.

So how he had managed to talk himself into telling Blair that he had feelings for her was unknown. It didn't help that Serena said that she would help out, because she knew how Blair felt about Dan.

While Dan didn't want to know how the brunette felt for him, he couldn't help himself. He asked her, just out of curiosity.

Thankfully, curiosity did not kill the cat.

She felt the same way as well.


Dan could hear the girls walking up the stairs, their heels clicking on the marble staircase. His hands were somewhat sweaty, but he quickly wiped them down on his dress pants. He kept on saying his 'lines' over and over in his head, muttering them every now and again under his breath. But he was interrupted when he heard the door swing open, the footsteps stop and a small gasp.

Looking up, he saw Blair taking small steps inside her room, looking around.

Dan had managed to recreate a bit of Paris in her room (with a little help from Harold and Roman).

There was a stunned silence.

Licking his lips, Dan eventually gave Blair a smile, nodding at Serena, who eventually backed out of the room and left the two of them alone.

"Blair,"

"Oh my god, Cabbage patch…" she trailed off quietly.

"Blair," Dan repeated, with a slight sense of urgency in his voice.

"Oh my god, this is perfect," she was still in a state of shock. He couldn't blame her.

"Blair," he said once more, eventually placing his hand on her arm and moving around to look at her.

She looked up at him, giving him a gentle wide-eyed look. Her features were soft in the dimly lit room, and he could see the smile in her eyes.

"I've been told I have a way with words," Dan finally started, eventually taking both of Blair's hands in his own.

"But I've never felt so tongue-tied when it comes to you," he paused, if only to be interrupted by the brunette.

"Dan, please, don-"

"Let me finish," he uttered with a smile, pressing his index finger up against her lips. She simply nodded, Dan lowering his finger.

"I'll just say it. Because I know if I launch into a speech, I'll never stop talking. And we both know how often that happens,"

They both chuckled lightly, Dan moving his thumbs against the back of her hands.

"Blair, I've been falling for you. I can't say that I'm in love with you, because I don't know that yet. But all I know is that I love you enough to become over-protective and possessive of you. I want you to be with me, all the time. I want to hold your hand, I want to buy you gifts and take you out for dinner. I want to be dragged into boutiques and let you put on a mini fashion show for me. I want to go to events and parties with you on my arm. I want to be the one that you turn to when you think Serena won't understand. I want to be the one that gave up almost everything for you to buy you the dress that you wanted,"

The silence between the two of them put Dan so much on edge, he almost thought that he poured his heart out for no good reason. That was before he felt her press her lips slowly against his, her arms circling his neck and pulling him down.

"I need a matching clutch for that dress," Blair whispered with a smile.

Dan smiled, his arms circling the brunette's waist and pulling her close.

"Does it have to be red?" he murmured against her lips.

She hummed happily against his lips. "We can go shopping for it."


Blair's eyes fluttered open as she heard her alarm clock go off. Reaching over and switching it off, she yawned with her hand covering her mouth, eventually settling back onto the bed. Humming quietly, her lips curved into a smile as she kept the sheet to her chest.

Eventually turning onto her side, she saw the slumbering form of Dan Humphrey lying next to her.

He was smiling in his sleep.

"What are you thinking of, Humphrey?" she whispered quietly to herself.

Biting her bottom lip gently, she laid still in bed as she watched her lover, still deep in his slumber, wondering what he was dreaming of.

All she could have hoped for was that he was dreaming of her.

And he was.