I do not own these characters or the storyline. I am just using them for some creative fun. This is the story of Blair and Dan's first date (as I see it anyway). It does not necessarily spoil what's happening on the show or follow it too closely either. Let's just say that it starts after the last episode, "It Girl Happened One Night" but does not rely on it for plotline. I am toying with the idea of continuing this as a series…showing other "important" dates throughout their relationship.

The First

Their first date was nothing short of a dare. They had been at a coffee house deliberating over the merits of the seventh film they had seen together (still not friends). She had just finished explaining to him, again, how unrealistic it was that the hero would have been able to successfully woo the heroine. They were from different worlds, different philosophies, and different income brackets.

"You really think it is impossible that two people could come together and…" Dan re-started his defense.

"I didn't say that it was impossible, just highly unlikely. It would be difficult for him to show her something new, take her somewhere she hadn't already been, and help her grow. In order to win her over, he would need to make an impact, leave an impression. Given the situation, I just don't think it's probable," Blair searched for an example. "It would be like you and I, Humphrey."

"I'm sorry, you and I?" Dan's cup stopped midway to his mouth as his eyebrow arched and his voice went high.

"Oh relax," she rolled her eyes with an exasperated look on her face. "I mean, hypothetically, somebody like you would have a very difficult time wooing somebody like me."

"You're joking right?" Dan chuckled. "You do remember that Serena was my girlfriend for two years."

"You mean, Serena was your girlfriend for a month and then not, then again for a month, and then not, then again for a…"

"Alright," he interrupted with a half glare, half smirk.

"I'm just saying, maybe you shouldn't use her as your evidence of your wooing capabilities," a genuine smile played at her lips as she looked at him. "Don't let it get you down, Humphrey. Better men have tried and failed. You're in good company." Dan laughed. Had he not been spending so much time with her lately, he might have been offended by her comment. However, he now recognized this playful ribbing as a sign of…an affection of sorts from Blair. If he had had pigtails, he was quite certain she would be pulling on them as she spoke.

"You really think I don't have what it takes to…"

"I know it," she nodded with a smile and a curt nod. She truly enjoyed sparring with him, more than she had ever guessed she would.

"Sounds like a challenge to me, Waldorf," his face grew serious.

"A challenge?" One perfectly sculpted eyebrow shot up.

"I do believe that, given a fair shot, somebody like me could woo somebody like you," he knew he was playing with fire, but he didn't care. If he was completely honest with himself, he would admit that these last few months, seeing movies and going to art exhibits with Blair, had been the most fun he had in a long time. And it was certainly the most 'him' he had been in a long time.

"You want to take me on a date? Why Humphrey, I had no idea." She tried to muffle a laugh.

"Ah, come on Waldorf, what are you afraid of? Think I might tarnish your image? Scuff your shoes?" His posture straightened as he tried to sort out how much of him wanted to prove her wrong and how much of him actually might want to take her out on a date. "Or are you just scared that I might actually prove you wrong and leave you quite smitten with me?"

"Smitten is not something I do," her eyes narrowed at him, not wanting to back down from a challenge. "Neither is scared," she took a drink of her coffee and met his eyes. "Fine. One date."

"One date?" He smiled as the words left his mouth.

"You have may have one date with me so that I can prove my point," though her eyes were steady and her voice never wavered, her fingers played nervously with the hem of her blouse. Dan watched her, silently, and then moved forward, letting his elbows rest on the table.

"I don't know Blair," his voice was low while he contemplated. "I'm not sure if you have the ability to be unbiased in your judgment. No matter what I do, you would never admit that you were wrong and I was right."

"I see your concern," she nodded, eyes cast down. "And I will be the first to admit that, in the past, I have been known to be…"

"Deceptive?" He tossed out, teasing.

"But I would like to remind you that it was you, not I, who took the most recent opportunity to sabotage."

"Fair point," he nodded and thought for a moment. "So, you'll be fair?"

"Of course."

"And honest?"

"Scouts honor," she held up her hand in oath.

"Then you, my non-friend, have a deal," Dan stuck his hand out. It was not lost on Blair that this was really one of the very first times that she and Dan had really touched.

"So, when would you like to have this…experiment?" She asked, turning her attention back to her coffee.

"Are you free on Saturday?"

"I am," she smiled. "Are you sure that three days are enough time for you to do your research and prepare to sweep me off my feet?" Dan laughed out loud before he moved in, closer to her and lowered his voice.

"I don't have to do research for this, Blair," her name on his lips caused her breath to hitch in the slightest. "I know you…I know you well. I know exactly what we're going to do."

"Oh?" Her voice came out smaller than she wanted.

"Can you be ready at three?"

"Yes," she nodded and cleared her throat, willing her voice to return. "Whatever shall I wear to this date?"

"Something you will feel comfortable in; both literally and metaphorically."

After agreeing that it was best to keep this experimental date from their friends, so as to avoid mass hysteria, Dan walked Blair home and then headed across the bridge. On his trip home, his mind couldn't help but run through his plan for the date. And he couldn't help but feel the slightest bit of excitement, wishing away the three days between him and Saturday.


It had begun as any normal day had. Blair had a hard time falling asleep the night before, jittery with anticipation. Eventually she was able to drift off to sleep. She woke feeling rested and rejuvenated and ready for her day. The weather was unseasonably warm, opening up endless possibilities of clothing options. And Serena, thankfully, had gone away for the weekend with Ben. Blair was more than happy to avoid the awkward explanation that would inevitably follow.

As the day passed and the hours grew closer and closer to three, Blair luxuriated in a hot bubble bath to ease her nerves and put her in the right head space. She stretched out and settled her head onto her pillow. She took a few slow, deep breaths and tried to clear her mind. The mixture of emotions she was feeling were a little confusing. There was a part of her that was gearing up for a challenge, a battle of sorts. But there was another part of her, somewhere deep inside that was eager for this date, even if it was only partly a dare. It had been so long since she had been out on a first date and, though she would never say it out loud, she was finding Dan more and more compelling as they spent more time together.

Though she had no idea what he had planned, she did know one thing for certain-her first date with Dan Humphrey was sure to be nothing like any other she had experienced. Her first date with Chuck-she couldn't even recall her first date with Chuck as their relationship had been tumultuous from the very beginning. Her first date with Nate was exactly what one might expect; simple, innocent, boring. Chuck and Nate were predictable. Chuck and Nate were from her world, where money and lineage meant something to somebody. Chuck was smooth, charming, and calculating. Nate was beautiful, well-bred, and well behaved.

But Dan, Dan was different. Dan was smart and witty and not at all intimidated by her. Though he now had quite a bit of money at his disposal, he was seemingly unaffected by it all. Though he could rightfully be living the life in the Upper East Side with his father and Lily, he chose to stay in Brooklyn. He knew exactly who Blair was, good and bad, and he still had every intention of showing up at her home to take her on their first date.

After trying on twice as many outfits as she normally did and three times the amount of shoes, Blair was dressed. Pretty. Casual-well, as casual as she was willing to go for a date, even an experimental date with Dan Humphrey. Dorota appeared, looking quite pleased, to announce "Mr. Dan's" arrival. With one last, shaky breath, Blair gathered her bag and took steps closer to Dan and their very first date. As she rounded the corner on the stairs, she couldn't help but critique his outfit. Amazingly, she was pleasantly surprised. He looked…good. She smiled. When looking at him through the fresh eyes she was forcing herself to use for this date, he looked good. It was then that he chose to turn and look up at her. If she had been paying attention, she would have seen his eyes widen slightly as he took her in, she would have heard his breath hitch the tiniest bit and she would have sensed that his heart rate had picked up the pace. She would have known that he suddenly felt nervous and a little…scared…about what this experiment might end up revealing. Nevertheless, Blair was too caught up in the warm, friendly smile on his face to even register anything else.

As she reached the bottom of the stairs, Dan, finally breaking from his trance, took a few steps toward her.

"Blair," he breathed. "You look…amazing."

"Thank you," she smiled and stopped in front of him. "You look…perfectly acceptable."

"I'll take it," he couldn't help the grin that appeared. He put his hand behind her, guiding her towards the door.

"What? No flowers?" She raised an eyebrow, half joking, half provoking.

"You know, I thought about it. But I ultimately decided that flowers are not exactly original and I think that, over the course of the day, you are going to find that I am nothing like any of the men that you have dated," he helped her with her coat as they waited for the elevator. Blair laughed lightly.

"This is something I already know," she pointed out.

"Yes," he nodded as the doors opened. "But, by the end of tonight, I'm going to have you convinced that it is a very good thing."

"We'll see," she put on her most seductive smile and walked right past him into the elevator. He watched, rooted to his spot, as she moved. He gulped the lump in his throat and suddenly became very nervous, not entirely sure what they had gotten themselves into.

They emerged from the building onto the walk. The sun was out and it was relatively warm. Blair scanned the street, looking for some mode of transportation. Dan, sensing this, cleared his throat.

"We're walking."

"Walking?" Blair couldn't help the inflection in her voice. "You can't be serious. First no flowers and now this? You are not off to a very good start."

"You know, Blair, you said you would give me a fair shot, but so far you've been treating this like a food critic treats dinner at a new restaurant. You're taking notes and making mental deductions. But you're never going to be able to enjoy this if you keep doing that. If you are really going to be fair, you're going to have to allow yourself to relax…and trust me," his eyes were wide and pleading and, for the life of her, she couldn't help but be swayed.

"Trust you…" She trailed off in thought. Taking a deep breath, she did her very best to relax and let her mind clear. "Okay, Humphrey, we're walking."

"Fantastic," he clapped his hands together and smiled. They began walking. From the very first step, they were already in sync with each other. "Now, the walking does have purpose."

"Oh?" She smiled genuinely.

"Our first stop is nearby and, along the way, I have something…or some things I want to show you," he explained, pulling a map of sorts from his coat pocket.

"What's that?" She eyed the folded up paper in his hand.

"This…" he held it up, "is a map of historical and architectural landmarks in the area. I know you appreciate art and history and architecture. So, on our way to our first destination, I thought we could check out some of these places."

"Hmmm…" She smiled, interested. "Can I see the map?"

"Of course," he handed it over as he came to a stop in front of a coffee shop. "But first, let's grab some coffee for the journey."

"Let's," Blair nodded as Dan reached to open the door for her. With a bright smile that had no hint of sarcasm, she stepped through the door. "Thank you."

"You're welcome," he grinned as he watched her walk past him, the smell of her hair as she breezed by sending a small shiver through him. He couldn't help but chuckle as he was quite certain that this was the first time that particular exchange of words had ever passed between them.

Once they had coffee in hand, they began their walking tour of historical and architectural landmarks. Blair was surprised to find that Dan knew quite a bit about the buildings and their designs, more so then the map explained. As he told her about the architects, the original intent, and the eras from which the designs were based, Blair was not at all surprised to find that she was enjoying herself. She hung onto every word, followed where he led, and studied the specifics he pointed out. She found that, when they came to their final stop, she was sad to have the tour end.

"Here we are," Dan gestured towards the building, which she now knew was a historic townhouse.

"Rizzoli's?" She turned to him.

"Rizzoli's bookstore," he smiled and reached for the door. "You haven't been here before?"

"I haven't," she shook her head, stepping into the beautiful building. She instantly loved it. It was warm, charming, inviting. She was impressed at how they were able to cram stacks and shelves of books into this old townhome without taking away from the beauty of the place, without taking away the feeling of…comfort. She paused in the entry way, taking in the woodwork, the staircase, the amazing ceiling, and the books. The books. "You brought me to a bookstore…" She trailed off, taking slow steps into the room.

"Not just any bookstore," his voice was low, soft as he leaned closer to her, "this is my absolute favorite bookstore. I could literally spend hours here…holed up in some nook reading or sorting through the stacks. They have the best selection…stuff you cannot readily find anywhere else."

"What are we going to do here?" Her voice sincere and interested instead of sarcastic and accusing.

"Two things," his smile widened as he realized she was truly enjoying herself.

"Two?" Her voice was just above a whisper as she turned to look at him. She gasped slightly as she realized how very close he was standing in that moment.

"Yes," he nodded, smiling warmly and not moving an inch. "First, we have to go up to the third floor."

"What's on the third floor?" Her eyes searched his for a hint.

"The children's corner," he grinned.

"Why are we going to the children's corner?" She laughed.

"For Story time," he answered as though it were the most logical thing in the world. Not waiting for her response, he took a step forward and then, reaching back to take her hand in his, he gently pulled her towards him. "We better hurry; you do not want to miss introductions."

She wasn't sure if it was the idea that they were going to story time or if it was the way her heart fluttered when he reached for her hand, but either way, she lacked the words, or breath, to respond. Instead, her smile deepened, and she followed him towards the stairs.


Story time was amazing. Blair had been a little cautious at the beginning, but as they sat together, leaning against large pillows against the wall in the children's corner, she was converted. The storyteller had begun by having everyone introduce themselves using their name and an adjective that described them and started with the first letter of their name (Bold Blair and Dopey Dan-which caused Blair and all the children to laugh out loud). Then, after everyone settled, she began telling stories—using amazing voices and dramatics. Blair was enthralled. Dan watched her as she seemed just as drawn in to story time as the children were. Her eyes were wide and bright and her smile was real. He couldn't miss the warmth he felt just watching her enjoy herself. He almost couldn't fight the urge he had to warp an arm around her and pull her close. But, not wanting to pull her away from her fixation, he refrained.

When story time ended, the storyteller brought out a record player and asked the audience to rise to their feet and dance to their good-bye song. Dan was completely shocked when Blair rose to her feet and held her hand out to him, insisting they participate. How could he refuse? He was thrilled to watch her as she danced about with the children and their parents. She looked stunning as she smiled and laughed and clapped her hands together. She looked…beautiful.

The music came to a stop and the parents gathered their children. Blair turned to Dan, who still seemed to be mesmerized by the music and the view.

"So?" She raised her eyebrows, looking a little like a child awaiting a surprise.

"So?" He smiled.

"You said we were going to do two things here," she explained, looking around her.

"Ah, yes," he nodded and gestured for her to follow him. And she did, to the top of the stairs, where he slowed to a stop and looked around the store. "Take your pick."

"Take my pick?" She looked around the room, confused. "I'm not sure what you mean."

"Well," he started, moving closer to her. "You pointed out earlier that I failed to bring flowers, which was actually a purposeful oversight on my part."

"You said that you weren't going to be like any man I've ever dated before," she reminded him.

"Yes I did," he grinned. "And I'm not. And, in that spirit, instead of flowers, look around the store and take your pick."

"Of the books?"

"Anything you like," he nodded.

"Instead of flowers, you're buying me a book?" Her eyebrows raised and for the briefest of moments he was worried he had made a fatal error. But then her face softened and her eyes brightened. "Dan, you are going to buy me a book?"

"That's the idea," he shrugged. "So, let's look around…take your time too, there are lots of nooks and crannies with some amazing finds…and, when you find the one you want…it's yours."

"Dan…" The way she said his name registered in the pit of his stomach. "Nobody…no date at least, has ever bought me a book. I don't know what to...how long do I have, to pick one out?"

"You can have as much time as you would like," he smiled. "As much time as it takes."

Had he been paying attention, he would have seen the way her eyes fought to hold in tears, he would have seen the way she very discreetly bounced on her feet in excitement. As it was, he wasn't paying attention, he was too caught up in the way his close proximity to her made his blood race and in the way he was no longer even thinking about the dare that had brought them here. Now, it was all about bringing this smile to her face.

"Well, don't just stand there, Humphrey," Blair waved a hand in front of his face. "We have shelves to explore."

And with that, he followed. Happily, Dan followed as Blair made her way through shelves and stacks of books, discussing their respected lists of literary classics. There were moments of laughter, moments of banter, and even moments of contented silence. Occasionally she would pull a book from a shelf and, holding it in her hands as if she were judging its weight, she would hold an internal debate-ultimately deciding no and returning the book to the shelf. Dan was delighted by the way she undertook the task of selecting a book. She was not quick. She was not rash. She was deliberate, thoughtful and careful and took great care in her selection.

Happily, Blair led Dan through the bookstore, finding great enjoyment in this treasure hunt of sorts. She had to admit that this date had so far, been quite satisfying. She loved that he had the insight to forgo flowers and offer her something with so much more purpose; something that had lasted for years and would continue to last for many more, something that was permanent and beautiful and all of her choosing. She smiled to herself as she thought about Chuck and how he would never have stepped foot in this bookstore. She chuckled as she thought about Nate who…well, let's face it, she didn't see shelves of "Cliff's Notes" anywhere.

They were exactly thirty-two minutes into the search when she found it. They had fallen into a happy silence when suddenly; she drew in a breath, causing Dan to look to her in alarm.

"I found it," she spoke with reverence as she pulled the small, leather-bound book from the shelf. Her small fingers traced the design on the cover and opened it to scan the pages. She smiled and nodded and then, meeting his eyes, she held the book out to him.

"This is it?" He asked reaching for the book. She nodded. He read the title and smiled wide. "A Separate Peace…"

"John Knowles."

"'But by now I no longer needed this vivid false identity; now I was acquiring, I felt, a sense for my own real authority and worth...'" Dan quoted the novel.

"'Finny's life was ruled by inspiration and anarchy, and so he prized a set of rules. His own, not those imposed on him by other people…'" Blair answered with a quote of her own. A quiet moment of reverence settled over the two of them, their eyes locked and their lips smiled.

"Excellent choice," he was the first to break the silence.

"Thank you."

"So…how do you feel about dinner? Are you hungry?"

"I am," she smiled and then looked around. "But first, I would like to stop at the ladies' room."

"Towards the back," he pointed past her. "You go ahead. I'll take care of this," he held up the book. "And I'll meet you at the bottom of the stairs?"

"Great," she answered and then, with more difficulty than necessary, she stepped away from him. He watched as she walked away. He watched until she was out of sight before he turned towards the stairs to purchase the book.

When Blair returned from the ladies' room, Dan was waiting, as promised, at the bottom of the stairs, bag in hand. He greeted her with a warm smile as she descended the stairs.

"I think I remember you mentioning dinner?" She raised an eyebrow.

"I did," he nodded and then offered his arm. "Shall we?" She hesitated for the slightest of moments before linking her arm through his.

"Do you want me to carry the book?" She eyed the bag in his free hand.

"Nah," he shook his head with a grin. "I think I can handle the load."

"How about the map?" She asked, fully expecting to continue their walk.

"The map?" His eyebrows twisted in confusion before it dawned on him. "Ah, the map. You enjoyed that, did you?"

"I'm not ashamed to say I did."

"Well, Miss Waldorf, I would be happy to continue the architectural tour of New York with you, but it will have to be another time," he moved away from her then, and she instantly missed his warmth. Dan nodded and moved towards a car waiting by the curb with a driver. "But we are done walking for the evening."

"A car, Humphrey?" She couldn't help the smirk on her face. "I thought this sort of thing was against all you stood for."

"Ha," he laughed. "I suppose I may have said that at one time. But, tonight is different…that, and I have it on pretty good authority that showing up to Per Se in my classic is simply not allowed." He opened the door to the car and stood aside, waiting for her to enter.

"Where?" Blair asked, rooted to her spot. "We're going to Per Se for dinner?"

"Yes," he couldn't help the self-satisfied grin that took over his face.

"But I've wanted to go there since…" She trailed off and looked him over.

"This I know."

"But how did you…" She slowly began moving towards him and the car.

"I listen when you speak, Blair," his voice was serious and hit her with impact. Despite the warm weather, she felt a chill. She had to swallow the lump in her throat. She was not used to people listening when she spoke, unless she was screaming. She hadn't felt listened to for much too long. Dan studied her face as a whole host of emotions passed across. "Are you okay?"

"Yes," she nodded and smiled warmly at him. "Yes, I'm ready." And with a newfound sense of confidence and worth, she moved to get into the car, stopping to place her hand over his as it rested on the door. "Thank you, Dan."

"You're welcome," he breathed, waiting until she was settled inside before joining her and pulling the door shut.

Dinner was everything that it had been hyped to be. The service was the epitome of great service. The food-positively ravishing. Blair felt gluttonous as she savored every morsel of her meal. The conversation was engaging, but it had always been so between the two of them. Almost always Blair found herself to be extremely stimulated by Dan, intellectually. She could talk to him about all of the things that were of importance to her; films, literature, history, current events. Of all her friends, he was above and beyond the most intelligent and well-read of the group. His company had grown more and more welcome over the last few months. And now, sitting across from him at Per Se after finishing a lovely meal, she felt satisfied; literally and metaphorically, and she was unbelievably thankful that they had been the only two left in the city during the holidays…otherwise they might never have forged this…friendship. And, after the day she had just had, that would have clearly been a tragedy. She had really had a wonderful day and, after Dan had handed the signed receipt to the waiter to pay the bill, Blair felt compelled to tell him.

"I have to admit, Humphrey, you have surprised me for sure," she tilted her head to one side, leaning closer to him from across the table. "Today has been really great."

"While I am pleased to hear that," his smile was wide. "The date is not quite over yet."

"Oh?" She was intrigued. "Where are we going next?"


While Blair had initially felt the reflexive need to protest, giving Dan the benefit of the doubt, she stifled her words. She was going to go against every instinct that had been bred into her and trust him. The drive across the bridge was a short one and Blair, for her part, had settled into her seat, satisfied, and watched the lights of the city speed by. When they arrived at the Brooklyn Promenade, she didn't hesitate to take his extended hand and step out of the car. And, when he didn't immediately drop her hand from his hold, she didn't hesitate to tighten her hold just slightly.

After purchasing two cones from the Brooklyn Ice Cream Factory (Chocolate Chocolate Chunk and Strawberry, respectively), Dan and Blair strolled along the promenade; her arm linked through his. They stopped to look at the New York City skyline and the only words that passed between them were when Dan would remember something about one of the buildings across the water. He would point to the building, tell her the tidbit. Blair would smile at him and nod and then they would return to the silence. Both were too caught up in what might be happening between them, the unspoken part of the night, to speak of much else. Dan was overwhelmed by his instinctual desire to be closer to her and struck by a kind of sadness that they may have missed out on this…moment…that they may have been wasting time pretending to be non-friends. Blair was trying desperately not to think about the tremble she felt every time he touched her. She was trying to avoid that familiar pull in her heart that usually hurled her head first into giving up herself to somebody else. It had almost been the destruction of her when she had been with Chuck. And, though she had managed to move on from him, she couldn't help but be a little afraid. She kept trying to convince herself that what she felt was happening between her and Dan was only a result of his effort to rise to the challenge she had presented—that there were no real feelings involved. But, every time her eyes rose to meet his…that argument was shattered and she was left with the need to hold onto him and not let him go.

They finished their cones at about the same time and, wordlessly, started back towards the car. It was only after they crossed the Brooklyn Bridge on the way home that she found the courage to speak again.

"Dan…" She turned to him, just as he opened his mouth to say,

"Blair…" They both chuckled lightly. "You go ahead." He offered.

"I think that perhaps…maybe…there could be the slightest chance that you were right."

"Right?" He raised an eyebrow, confused. "I'm sorry, you lost me. I was right about what?"

"The…" She searched for the right words, growing sad as she remembered the true origins of this evening. "The dare…the challenge. You may very well be correct."

"Oh, that," he ran a nervous hand through his hair as he studied her face for some sort of sign. "Are you saying that there's a chance that somebody like me could woo somebody like…"

"Me?" She interrupted, feeling her walls of defense shooting up for the first time that night. Her eyes grew hard and she shrugged. "Maybe a more simplistic version of somebody like me."

"Of course," he chuckled, feeling a little defeated, despite his victory. "Of course. But not you. Not Blair Waldorf." His eyes looked away from her then, finding solace in watching as the car pulled up outside her building. Without looking back at her, he stepped from the car and offered his hand. She accepted and joined him on the walk. She watched as he moved to the door of her building.

"You don't have to do that, you know," she called out to him. "You don't have to see me in, since it wasn't a real date anyway." And that did it. His eyes grew a little angry and his posture stiffened.

"A real date?" He laughed. "I'll tell you what, Blair Waldorf, until you just brought it up, I hadn't thought of the dare all night. I truly had a good time with you tonight and I thought that you…God, I am so stupid, I thought that you were genuinely enjoying yourself…you know what, it doesn't matter. I am not going to leave you standing here on the street. I'm going to walk you to your door because…because that's who I am." He held the door open, but she stood, rooted to her spot, unable to move. "Are you coming?"

"Did you mean it?" Her voice was small and there was something in her eyes that made it seem like the answer to this question just might make or break her.

"Did I mean what?" His posture softened a little.

"What you just said…" She cleared her throat. "That you hadn't thought about the dare all night?" She raised her eyebrows, hopeful.

"Blair," he sighed and let the door close, moving towards her. "I…yes…this whole evening…I, well…yes. Yes, I meant what I said. I'm not sure exactly when it…shifted…but I haven't," he took a deep breath, at a loss for words at the moment. "Yes, I meant what I said." And then he watched as her face changed, showing what her brain was most likely processing. And then, she looked away from him, starring down the block, looking into nothing, taking steadying breaths. "Blair? Are you okay?"

"Yes," she whispered, looking down at the ground. Then, taking a deep breath, she met his eyes. The depth he saw there caused his breathing to stop. "Me too."

"I'm sorry? You too?" He managed to find his voice.

"I hadn't thought about the dare all night either," she explained, a small smile on her face. "I mean, at the very beginning I was thinking about it, but then you told me to relax and trust you…"

"And you did…" He smiled.

"I did," she nodded. "And I truly had an amazing night. It was…the walk, the bookstore, my book," she held up the bag in her hands. "It was a lovely day, Dan. That's what I meant to say in the car. It was a lovely day. Thank you."

"Well, you're welcome," he softened. "Now, are you going to allow me to walk you in?"

"Of course," she nodded and, finally, stepped from her spot. Silently, she passed by him holding the door. Silently, they entered the elevator and he pressed the button to her floor. Dan was trying desperately to read the mood, to figure out what was being left unspoken. But, for the life of him, he didn't know. He was caught somewhere between the old Blair Waldorf who he had known, but barely known in high school, and this new Blair Waldorf who was his friend…who he had grown to know and care about. And, from the way things had just gone, he was guessing she was caught somewhere between the two as well.

The elevator slowed to a stop and the doors opened slightly. They stepped into her foyer and Blair turned to him with a small, nervous smile.

"Well, here I am," she glanced around, taking note that they were most likely alone.

"Yes," he nodded and clapped his hands together. "Well, thank you for going out with me tonight, Blair."

"Dan…" She spoke his name softly as she moved closer. "Thank you for…for proving me wrong." And then, completely unexpectedly, she leaned in and placed a soft kiss on his cheek, stunning him into silence. His skin felt like it was radiating from the spot where her lips had touched him. When she pulled away, her eyes were warm and her smile was sweet. "Goodnight."

"Goodnight…" He muttered, turning towards the elevator as Blair turned to remove her coat. His mind was numb as he moved to step into the elevator. Then suddenly, it was like something took over his body and forced him to turn back to her. "You know…" he called out, causing her to turn back to him. There was a small gleam in his eye as he smiled at her. "You know, you did say that I won."

"You won?" She raised an eyebrow as a smirk played across her lips.

"The challenge," he explained. "You said that I was right; that I won the challenge."

"And you said that you didn't think about the challenge the entire day," she crossed her arms, smiling.

"And I meant it," he grinned, happy to see that they fell back into the banter easily. "But I do think that, given that it started as a challenge—a challenge that I won—that I should get some sort of…reward."

"You think you win a prize?" She laughed. "What kind of prize do you think would be appropriate, Humphrey?"

"Well, I'm not sure what would be appropriate," he shrugged and then, taking a deep breath to calm his nerves, "but I would settle for a second date."

"You would settle for a second date?" She asked, making sure she had heard him correctly over the sound of her pounding heart.

"Yes," he nodded, moving closer. "Except that it wouldn't be a dare…and it wouldn't be settling."

"You want to take me on a date…" She fought to keep the giddy smile from exploding on her face; fought to maintain control.

"I do," he nodded, laying it all on the line. "And you know what, I think you want me to take you on a date."

"Is this some sort of game?" She arched an eyebrow.

"I don't play games, Blair." He held her gaze and smiled at her. "Today was…today was great and now, I'm asking…would you like to go out with me again sometime?" He watched her, half expecting a denial and half expecting some sort of harsh witty response.

"You know," she smiled shyly at him. "You know, I think I would."

"Really?" His grin widened.

"You thought I would say no?"

"I thought there was a chance," he admitted.

"Were you hoping I would say no?"

"No, of course not…" He shook his head, trying to regain control of the runaway conversation. "I was hoping you would say yes."

"Well, I am," she nodded. "I'm saying yes."

"How is next Saturday?"

"Perfectly free."

"Can I call you this week with details?"

"You should call me this week with details."

"Okay," he clapped his hands together, unashamed at how happy he felt in that moment.

"Okay," she smiled, feeling sleepy and content.

"Well, goodnight Blair," he moved again towards the elevator.

"Goodnight Dan." And then, with a warm, contended smile and a full, happy heart, Blair watched as the doors closed between her and Dan. Only then did she turn and make her way, slowly and happily, up the stairs to her room.


Okay…please let me know what you think. I thought I might do a series of "important dates" between the two of them….but only if you want to see it Also, the bookstore is a real place. You can google it. And I took some creative freedoms with where things were actually located in NYC…so if I'm wrong about it…forgive me.