So happy to hear you guys like the story so far! Thank you so much for leaving reviews and feedback :) Quick note on the flashbacks, they are all in chronological order. I'll update again by Wednesday evening. Thanks for reading!

Three Years Ago

Dan and Blair stood off to the side, both enrapt in people watching. They were at a charity silent auction accompanied of course, by Nate and Serena. Both of their friends were far more interested in bidding than either of them. It struck Dan then how similar Nate and Serena were. They both often had expressions of childlike wonder on their faces, were easy going, and charmed those around them.

Blair leaned in suddenly, the slightest trace of Chanel No. 5 wafting along with her. She whispers, "What do you want to bet Serena bids on jewelry worn in a movie or by a celebrity?"

"What do you want to bet Nate bids on a yacht or sailboat?" Dan counters.

Blair sticks her well-manicured hand out, "Deal."

Dan takes her hand and shakes it firmly. "Our friends are so predictable."

"What if we both are right?" Blair asks as the thought seems to strike her. Her eyes narrow, "Also, what exactly are we betting on?"

Dan thinks for a moment. An idea forms, "If I'm right, you go with me to the typewriter exhibit I told you about."

Blair wrinkles her nose, "Ugh, I better get my oversized cardigan and wide-rimmed glasses ready. That's bound to be hipster central. But fine."

"And if you win," Dan continues, "I go to one fashion week show of your choosing."

Blair seems delighted by this idea and he watches her stifle a laugh. "Deal."

"If we're both right, then we do both." Dan finishes.

Blair gives him a rare smile and compliment, "Good plan Humphrey. I must say I am somewhat impressed."

"Guys, look at this!" Nate exclaims. Both Dan and Blair turn to see what he's looking at. Nate leans forward and reads from the poster, "The SS Recess: Your sea-set home away from home. How much should I bet?"

"Don't worry Waldorf," Dan looks over at Blair as Nate scribbles down a number. "We'll go to Urban Outfitters before the exhibit."

"That's not even a good boat name," Blair says, unamused. "He should rename it." Dan watches her eyes flick towards where Serena stands, reading something. "What are you looking at, S?" She asks, innocently.

"A 14-carat gold serpent cuff worn by Elizabeth Taylor in Cleopatra." She says in awe. She starts to pick up the pen next to the bid sheet.

"Our friends are tragically predictable." Blair sighs.

"I bet that'll go for a lot. Probably more than all the Louboutins in your closet, combined. Safer not to bid." Dan says to Serena in his most earnest tone.

Blair jabs him with his elbow. "Cheater." She walks over to Serena. "Wow, so gorgeous. I mean, you have to bid on it right? It would be a crime not to."

"True." Serena writes down her bid. Blair turns back and gives Dan a wicked smile.

Once she's near him again, she says, "I'm sort of thinking a Kate Spade show might be perfect for you. It's presentation style so you'll actually have to walk around the room to see the full collection. That way you can truly be present. Oh and we can stop by Jack Spade first to get you all preppy for the show. We can coordinate outfits."

"I can hardly wait." Dan's lack of enthusiasm elicits a beaming smile from Blair. He realizes then with surprise, that the idea of hanging out with Blair alone doesn't actually horrify him. It was odd to think how just a couple of weeks ago, he would run from any solo encounter with Blair Waldorf. How at the museum, he had nearly fled when he saw just her. But now, he didn't dread it at all. Not one bit, in fact.