When Humphrey Met Waldorf

disclaimer: i don't own gossip girl

an: slight s4 spoilers. depending on reaction, i have the story planned out. let me know what you all think!


The first time Dan almost kissed Blair, spring internships had just come to an end. There was nothing left to do but celebrate new beginnings. So, there they were on a Tuesday evening, seated in an intimate booth in Le Bernardin with a bottle of wine and scant portions of (in Dan's opinion) overly-priced hiramasa.

Taking a sip of his pinot noir, Dan couldn't help but be mesmerized by the way Blair ate, all dainty and methodical.

Like her, Dan supposed.

One curious thing about Blair's eating habits, though, was that she was apt to consume more - lots, even - when she was at ease. Oddly enough, to Dan, that seemed only to be when Blair was around him, of all people.

And at that moment, her plate was nearly empty.


As the night ticked on, Dan found the conversation to be relaxed, effortless, mutually understood. Resting his chin on his hand, a lazy grin on his face as he listened to Blair opine about transcendentalism, Dan was content.

"...so Thoreau's wife was like, 'Where's Walden?'" Blair finished, a muted excitement lacing her voice.

Dan cracked up.

"Wow, Blair Waldorf has jokes," he teased.

"Oh, absolutely," Blair smiled smugly. "They aren't as funny as that tie looks on you, though."

"Hey! What's my tie collection ever done to you?" Dan frowned, feigning hurt.

Blair cocked her head as she quipped, "Assaulted my vision, Humphrey. I believe you know that by now."

Dan didn't bother to be insulted. In fact, he was downright pleased at the fact that they shared an inside joke. Besides, he knew her humor by now, and so he countered, "Would bow-ties be better suited to your oh-so-refined tastes?"

"Very funny," Blair said dryly, rolling her eyes. "And no, they would not. Bow-ties are so last season."

"I'll toast to that," Dan said, lifting his glass.

"I'll do you one better," Blair announced jubilantly, a mischievous sparkle in her eyes. "To bright futures and the evolution of your sense of style!"

"You just couldn't resist, could you?" Dan chuckled as he drank from his glass. He rested his elbows on the table, laced his fingers together.

There was a beat of silence.

Blair's smile faded. "How could I?" she murmured, a faint (and beautiful, as Dan noted) blush racing to her cheeks. She hastily added, "While your affection towards plaid is hardly something to boast about, at least you're wearing Tom Ford instead of Target."

And right then, despite Blair's defensive quips, Dan knew.

He leaned forward slightly, tie brushing the table. "You know, I really enjoyed working with you this semester. Seriously."

Blair met his gaze as she ran her index finger around the rim of her glass. "Surprised, are you?" she asked sarcastically.

"Well, yeah," Dan admitted, heat creeping up the back of his neck. "More than pleasantly, though. You were – are – great."

Eyes widened. Blair dropped her head, curls veiling her face.

Dan felt stupid.

His hand darted towards his wine glass, but before he knew it, there was another on top of his own.


Dan turned his head, utterly confused by the physical contact when she'd emotionally just rejected him.

"So were you," came a faint whisper.

"What? I couldn't understand you," Dan said, straining to hear Blair.

"I said, so were you," Blair huffed, crossing her arms. Voice lowered, Blair added hesitantly, "Great, I mean."


'Oh'? Really, Humphrey?

Stomach knotting as Blair nodded, Dan was conflicted. In the back of his mind, there was that little image of Serena, but in the front…

In the front was Blair Waldorf. His contemporary, his intellectual equal, his – well, his crush.

Dan's mind was made up as he observed the way Blair instinctively leaned towards him. Eyes closed, Blair's body a magnet to his own, he was going to do it.

He was going to kiss Blair.

Was, being the interpretive word, because their waiter seemed to possess the curious knack of interrupting at inopportune moments.

Blair pulled back as Dan cleared his throat and shot the interloper an accidental glare. Slicked back hair and a pompous grin told Dan the guy was clearly self-important, meaning he didn't give a damn who he was interrupting - or what.

"I'll be back for this in a few minutes, monsieur," the waiter said smarmily, his thin mustache curling up with the curve of his greasy smile.

Dan nodded, smiling tightly. "Right," he replied, voice calm.

In reality, his blood was boiling. He'd taken a gamble – a word that definitely wasn't present in the Humphrey Dictionary of Moral Integrity – only to have the attempt thwarted by a modern-day Gaston.

"It – it probably wasn't a good idea, anyways."

Dan's eyebrows shot up, surprise written all over his face at Blair's sudden comment. "What? Why?"

Blair gave him an incredulous look and counted off her fingers, "There's Serena, and there's Gossip Girl, and there's –"

Holding up a hand - not bearing to hear anymore reasons why Blair found him so unworthy – Dan interrupted, "I get it, okay? You're right. We were completely, out-of-our-minds stupid, and it won't happen again. I'm sorry."

The expression on Blair's face registered hurt at his (fake) agreement, but she clutched the handles of her purse with a forced smile. "Good. Because we are friends, and friends don't kiss. And don't worry about the check, Humphrey. With Lily and Rufus fighting all the time, who knows for how long you'll have access to her fortune."


That one hurt.

As Blair slipped a wad of cash in the black bill holder and stalked towards the exit, Dan literally felt sick to his stomach. Why was Blair so mad that he told her what she wanted to hear?

Opening his wallet, Dan gazed at the hard-earned money inside of it. He wondered if he'd ever tell Blair how long he'd saved this semester to take her to somewhere this nice.