As Dan Humphrey rounded the corner of the bustling 6th Avenue he could already hear the sound of her heels clicking, impatiently. Of course, he wasn't within earshot of her, but knowing Blair Waldorf, four minutes late was enough to cause her to be jittering with annoyance. Spotting her just ahead, Dan was gratified to see he was right. There she was, her magenta suede Manolos tapping the ground anxiously. Spotting him, she narrowed her eyes and slouched in annoyance.

"There you are Humphrey, is it so hard to be on time? It's not like you take the time to make yourself presentable," She wrinkles her nose as she visibly scrutinizes his hair and then outfit. "So tell me what it is that caused you to be so late?"

"Hello to you too Blair," Dan says, handing her a ticket. "It's only four minutes after the hour."

"Five, actually." She says after scanning the face of her Cartier watch. "Let's go inside. You know how much I hate having bad seats. If I have to sit next to some greasy-handed person spilling their popcorn on me I will be irate."

"I don't doubt it." Dan follows her into the little independent theater. They head directly for the theater the movie is in and take their seats in an unoccupied row. "I told you it wouldn't be crowded. Do I need to remind you that not everyone is as particular as you about their seats to show up a full 45 minutes early?"

"40 minutes, given that you were 5 minutes late." Blair corrects and pulls down the armrest between them.

"So what do you suppose we do for the next 20 minutes?" Dan points out the stretch of time they now have to fill until the trailers start.

"What we always do, you tell me what you've been doing lately and I judge your lifestyle choices and then I tell you what I've been doing and you judge mine."

"Haven't I've been lectured enough today? First for my tardiness and then now for who knows what, maybe for choosing to eat again at the same Thai restaurant last night."

"Fine, we'll jump to mine. I broke things off with Finn."

Dan lets out a breath, "Finally. That guy was the worst."

"Tell me how you really feel," Blair rolls her eyes. "He wasn't that bad."

"Blair, his name was Finn. I mean, who willingly goes by that name?"

"It's short for Finley," Blair says in an obvious tone. "Anyways, aren't you going to ask why?"

"Hm," Dan strokes his chin, "He's leaving the East Coast to head west and study marine biology?"

Blair is unamused, "That's the best you can come up with? Your wit isn't nearly sharp enough today. Since you aren't going to ask, I will just tell you." She sounds irritated. "He texted me 'What's cooking good looking?' It ended right there and then."

Dan bursts out laughing. "Okay, that is truly terrible. Even if he wasn't laden with a multitude of other flaws I would still encourage you to stop seeing him just for that."

Blair tilts her head, "I know. Did he see that on an apron and think, hm Blair will enjoy that greeting?"

"Apparently. Good call on kicking him to the curb. I approve." Dan nods vehemently.

Blair smiles, "Glad to hear it. Oh, look trailers are starting." She pokes him in his side, "See we didn't have to wait 20 minutes, you're so dramatic."

Pushing open the theater doors, Dan and Blair walk out to the city only bathed in streetlights. They pause on the sidewalk and Blair says, "I have to admit, that was better than I thought it would be. Actually, it was a solid movie."

"Wow, that's like a glowing review coming from you." Dan says and then softens his tone, "I'm glad you liked it too though."

"So I'll see Sunday." Blair says before she hails a cab.

"Of course, if you missed waffle Sunday I would be concerned."

"Actually, I think Rufus would be the one most concerned. Wasted waffles are the bane of his existence."

Spotting a cab, Blair steps off the curb and waits for it to come to a stop before climbing in.

Dan forgoes going back to his apartment and heads to the loft after to have dinner with his dad.

"You decided on Italian after all." Dan says as he walks in and is surrounded by the aroma of garlic.

"You can never go wrong with spaghetti and homemade marinara. How's my favorite son?"

"Good!" Dan says enthusiastically.

"What'd you do this evening?"

"Movies with Blair." Dan replies as he piles his plate with noodles and sauce.

"Didn't know an outing with Blair Waldorf could leave you so chipper. Don't you two thrive of turmoil?"

Dan rolls his eyes, "We get along 90 percent of the time."

"50 percent, I'd say."

"Fine 80. Anyways she finally broke it off with Finn so I am indeed in a good mood after hearing that news. I hated that guy." Dan shakes his head.

"So you've said before." Rufus eyes him curiously Across the table as he scoots in his chair. "Actually, that reminds me, I've noticed something."

Dan looks up from his plate, "What?"

"It's just that it seems like you never like any of Blair's boyfriends."

"Actually Finn didn't make it to boyfriend status, luckily." Dan points out as he winds up spaghetti around his fork.

"Exactly. That's what I mean," Rufus says animatedly "Why wouldn't you want Blair to have a boyfriend?"

"It's not that, I just don't want her to date some guy I can't stand."

"I think you're missing my point. I can't recall you ever liking a single one of her boyfriends and I'm starting to wonder if there's a reason for that."

Dan narrows his eyes, "What are you implying, Dad?"

"I'm not implying anything, just making an observation." Rufus shrugs and resumes eating his spaghetti. He doesn't bring it up again but the conversation lingers in Dan's mind for the rest of the night.

The rich, caramel scent of maple syrup wafted through the loft as Rufus began serving breakfast to Blair, Dan, and Jenny who were seated around the table. After he finished dishing up the waffles, Rufus took his seat across from Dan.

"So Blair, how have you been?" He asked, instantly sparking skepticism in Dan.

"Well, you?" Blair replies.

"Never happier than on Waffle Sunday. So how's Finn? That's his name right?"

Dan glares at his dad from across the table, not liking where this is headed.

Blair seems surprised by Rufus's mention of Finn but replies with zero skepticism. "I wouldn't know. We aren't seeing each other anymore."

"I bet Dan's relieved," Jenny joins in the conversation, further irritating Dan. "He hated that guy."

"So he told me about a million times." Blair rolls her eyes. "He wasn't that bad. I mean for someone who made quite a few questionable choices in dating he certainly is openly opinionated."

"Ah," Rufus says, eyes sparking with mischief. "Who are you referring to?"

Dan begins trying to telepathically send the message to his dad to stop immediately.

"Hmm," Blair tilts her head as she thinks. "Autumn was pretty insufferable. I mean, every time she saw me with a cup of coffee she told me it would give me cancer."

"She said that one time." Dan can't help but be defensive.

"Well if it wasn't about coffee then it would be about the toxins in my nail polish or the chemicals in cleaning products Dorota uses. She was the literal definition of fear mongering."

Jenny jumps in, "I agree with Blair. It was totally annoying. I mean, she literally tried to take out my hair extensions without my permission because she said it was damaging my hair follicles. Like, hello, are you my hair stylist? I don't think so, get your hands off my scalp!"

Blair laughs, "See, told you." She says to Dan. "Insufferable."

Jenny nods in agreement.

Suddenly, Blair's face lights up. "Oh but I almost forgot about one of his most unfortunate choices." She pauses for effect, "Pyramid Piper."

Jenny bursts out laughing "Oh my god, you're so right. Remember when she brought over all those candles to Waffle Sunday?"

"Or that time she walked in and stocked the juices in the fridge during Waffle Sunday, left an order form for us to refill when we ran out, and then just left? She hadn't even been invited over yet took it upon herself to come on in. Stalker status." Blair shakes her head.

Dan gives his dad a look to say, see what you've started?

"I mean how many pyramid schemes can one person be involved with within the span of three months? She must have broken some sort of record." Blair muses.

"Okay, Blair," Dan can't stop himself from saying something. "It's not like you haven't had a number of poor choices in dates. Didn't one guy take you to the Jersey Shore to 'widen your horizons'?"

Blair wrinkles her nose, "He tried to and I obviously did not go and then, promptly stopped seeing him. Unlike you, I know when someone's a dud. By the way, Rufus, you've been awfully quiet," At Blair's words, Dan feels a flood of relief. She's finally catching on to her dad's scheming. "Certainly you must have some input."

Dan visibly sags in disappointment. That was not the direction he had hoped that was headed in.

"Well, I think the two of you have a rather interesting collective dating history. I find it most interesting though, how little you two approve of one another interests when you are best friends."

"Best friends? I think that's a strong word choice. Dan, don't you agree?"

Dan nods.

"Well then, close friends," Rufus amends. "But it's a fair choice."

Blair shrugs. "I guess the real issue is that I chose to be friends with someone who has a terrible taste in romantic pursuits."

Dan narrows his eyes and then lets out a breath. "Well, I think that's enough walking down memory lane for one breakfast, don't you?" Then he quickly changes to subject onto Jenny's classes and the conversation is temporarily forgotten.

After breakfast, Blair and Dan head to his apartment to watch a movie. As soon as they are through the door Dan turns to Blair, "Did you have to give in to my dad's little scheme so easily?"

Blair's brow creases in confusion, "What do you mean?"

Dan exhales loudly, "Seriously? The whole exes thing was just to prove a point."

"Oh, he was awfully nostalgic this morning. What was that about?"

Dan debates whether or not to tell her but relents, "He said that you and I always find issue with each other's romantic choices."

"He's not totally off base with that remark," Blair says as she sets her coat down on the bar stool and then leans against the counter.

Dan runs a hand through his hair, "He implied, to me, that there's a reason for that."

"What reason? You have terrible taste and should hire a matchmaker? I could get on board with that."

"Blair," Dan is getting irritated. "The implication is that we don't like one another's choices because…" He can't bring himself to say it.

Realization washes over Blair's face, "You like me? Is that what you're saying? You like me and you don't want me to date-"

"No," Dan interrupts her. "I don't, don't flatter yourself."

Blair looks taken aback.

"That's just what my dad thinks," Dan continues. "He thinks we secretly like each other therefore we don't want each other dating anyone else."

"That's ridiculous," Blair says automatically.

"That's what I said but you going on and on about how terrible all my exes are didn't help to disapprove that notion."

"Well, how was I supposed to know that's what he was up to? You could have tipped me off."

"I didn't realize he would bring it up again." Dan hesitates before saying, "Anyway, I've been thinking about it and what if he's right?"

Blair laughs, "no way."

"But Blair, we can't name one ex that we didn't have a problem with."

"So? I don't think we should subject ourselves to analyzing his little theory."

"Why not?"

"It's like opening Pandora's box, there are only two possible outcomes. A) one of us discovers we do in fact like the other or worse yet love while the other realizes B) they have zero romantic interest in the other because of X qualities the other possesses and now they can't stop thinking about all those qualities they don't like. So inevitably we stop being friends."

"What if both of us reach the same conclusion?"

"It still ends either way."

"Even if both of us reach outcome A?" Dan can't bring himself to say like or love each other.

"Yes, it'd be destined to fail." She says in an obvious tone. "Because then there would be all this pressure to turn our friendship into something more. If it ends, then not only does the relationship end but also the friendship" Blair wrinkles her nose and shakes her head. "It's a bad idea, in fact, I think we should stop discussing this to be safe."

Dan thinks over what she says, "If that's what you think is best." He heads over to the TV to switch it on and start the movie. "Can I just ask you one thing and then we close the subject?"

Blair shrugs. "I suppose."

"Have you ever thought about it? About us?" Dan says, surveying her from across the room.

Blair doesn't respond right away and when she does, she reflects back the question. "Have you?"

"Not until today," Dan says which isn't exactly a lie.

"Me neither." Blair says matter-of-factly. "So, what are we watching?" Her question signaling the end of the conversation.

I hope you all like the concept of this story! I wanted to try something a bit different from what I've written before. So I figured writing from Dan's perspective would be a change and also having Dan and Blair already be friends would give them a different dynamic from my other stories. This story will also be interlaced with flashbacks so you'll get to see how Dan and Blair become so comfortable in their friendship.

Expect another update tomorrow :)