Their parents figure it out all around about the same time, although their reactions vary.
Dan's mother suspects when every phone call and email from Dan starts to contain a surfeit of references to Blair. She asks about school and he tells her that Blair has converted him to the pneumonic method of studying. She mentions seeing the new Colin Firth film and Dan says he was pleasantly surprised after Blair dragged him to it last week. She discusses her latest art project, and Dan can't seem to resist spouting a few of Blair's opinions on an exhibit they had recently visited. Finally, when she makes a tentative enquiry about his love life, he vacillates for a bit then says he thinks it's best that he's on his own for a while. Something Blair had said to him before Christmas has really struck home with him, and he feels he's in a place right now when he really needs to concentrate on his writing.
Dan further relates back that, by convenient coincidence, Blair's also decided that her focus for the moment should be on her career.
Alison, while not the most incisive maternal figure, knows the signs of a full-blown infatuation.
It worries her somewhat, because she wishes Dan would fall for someone closer to her own world, the world of Dan's childhood. Although it hadn't altered him the way it had Jenny, Alison had felt for years that he was slowly slipping away from the lifestyle, the routines, the people that she was familiar with, as he became more entrenched in the Upper East Side (despite his residential address). She had been overjoyed when he started dating Vanessa, a connection not only to the old world, but to her, as she had been friends with Vanessa's parents for years.
So she feels apprehensive about Dan's potential involvement with another member of the UES elite. At the same time she fears endangering the tenuous, long-distance relationship she has maintained with her son by verbalizing her concern. And she has to admit, even though this Blair Waldorf might not come from a world she understands or wants to understand, it is clear that – like Dan, and like herself – Blair has an appreciation for literature, art and film. More importantly, from the amount of time she has been spending with him, Blair obviously has an appreciation for Dan.
And at least this means he's no longer fixated on Lily's daughter.
Harold and Roman come to the realisation in much the same way, as Dan's name always seems on the tip of Blair's tongue, and he pops into the conversation for no apparent reason. A lot of the time it is only for Blair to make derogatory comments about his fashion taste or his flawed views on the Merchant Ivory masterpieces. But Harold still remembers how when Blair was a little girl she always used to scuff her dainty designer footwear kicking the shins of the boys she liked. (Nate Archibald and Chuck Bass in particular had sported colourful collections of bruises throughout their formative years.) So he and Roman decide they should definitely make plans to visit New York over the upcoming Spring Break, in order to properly inspect Blair's potential beau.
Harold mentions his theory in a phone call to Eleanor, but she responds with a disbelieving laugh. "Daniel Humphrey!" she chuckles, "He was a waiter at our Seder meal a few years ago. It may have escaped your notice, Harold dear, but our daughter is a bit of a snob. Blair would never date hired help!" Eleanor points out with wry affection.
She is forced to revise her opinion two days later when she takes a detour through Central Park, scoping out possible locations for an upcoming fashion shoot with her favourite photographer, and comes across Dan and Blair engaged in a snow fight.
The snow has stayed late that year, thrilling Dan who relishes the magical winter wonderland and delighting Blair with the extra opportunities this presents for ice-skating in the park. Dan is less happy about this prospect, as Blair has decided that it is her mission in life to teach him how to skate, something his uncoordinated body was never designed to do.
Dan is complaining about being dragged on yet another lesson, making sarcastic comments as he surveys the rink ominously with his back to Blair, when suddenly a snow ball hits him in the ear.
Stopping mid-rant, Dan turns to see Blair staring back at him beatifically, hands innocently clasped behind her back.
"Waldorf, did you, did you really just hit me with a snow ball?" Dan sputters.
Blair shrugs and smiles angelically. "Well, if you don't want to go ice-skating, we'll just have to find something else fun to do in the cold weather." And with that she pulls her hands around from behind her back and lobs another snow ball at him, getting him square in the face.
Dan immediately grabs a handful of snow and grins. "Not a good move, princess. As you love to remind me, I grew up on the big, bad streets of Brooklyn. Where you have to toughen up young cos' a snowball could hit you anytime, anywhere." He throws the ball at her.
"Ow!" Blair cries, rubbing her face. "It scratched my eye!"
Instantly concerned, Dan starts for her and reaches up to gently cup the side of her face. "Blair, I'm so sorry, I didn't mean to throw it so hard," Dan tells her mournfully, probably more anxious than the occasion warranted. Blair responds with a quiet whimper. "Here let me see," he sooths, moving in closer so his face is mere inches from Blair's.
Just then Blair reaches up to pull back his collar, and Dan is subjected to the unpleasant sensation of ice falling down his back.
Blair scampers to a few feet away from him, grinning in self-satisfaction. "You forget, Humphrey, I grew up on the Upper East Side, where we don't fight fair!"
Then they are chasing each other, around the park, ducking behind trees to avoid snow-balls and taunting each other as they take their shots.
"And you forget Waldorf that I grew up in the same household as Jenny Humphrey. What I lack in cunning, I make up for with endless amounts of patience," Dan informs her, having drawn her to within a few feet of him by concealing himself behind a food cart. He begins pelting her with a tidy pile of pre-prepared missiles.
"Truce, truce," Blair screams, as he wrestles her to the ground and threatens to pour snow down her Alexander McQueen cashmere cardigan. Dan hesitates briefly and Blair uses the opportunity to grab one of the balls of his pile, smashing it into his hair. "No truce, no truce," she shouts, as she squirms away from him while he shakes the ice from his hair.
Eleanor watches as a grinning Dan takes off after a shrieking Blair, her cheeks pink with excitement and fun, her brown curls flying in wild abandon. She has never seen her daughter so simply joyous.
"You see Eleanor," Leonardo, the photographer pronounces smugly. "Central Park has the right sense of romance, of whimsy, for your Spring line. It infects every couple who comes here!"
Eleanor surveys the darkly attractive pair assessingly. "Yes, Leonardo, I do believe it does," she finally murmurs approvingly.
Things have been tense between Rufus and Dan for a while.
Dan had not been overly impressed that his father had just handed over the keys to the loft to an ex-con and invited him to move in with his only son. And that he had then failed to mention this offer to Dan until he arrived home to find said ex-con in the apartment with his ex-girlfriend. Who it now seemed would be dropping by frequently because his new room-mate his also her new love interest. Just what Dan wants when he's trying to move on from the never-ending drama of their will-they, won't they relationship.
Dan has taken to avoiding both Ben and the loft. This is surprisingly easy to do, as he throws himself into school and the internship. And his new friendship with Blair. Actually, it is kind of ironic that most of the time while Serena is in Brooklyn with Ben, Dan is on Park Avenue with Blair. He considers asking Serena whether they should just swap rooms and have done with it.
But when his father asks if he can meet him in Brooklyn Friday morning for a traditional Humphrey breakfast, Dan agrees. He's not really the type to hold a grudge. Besides, he's pretty sure Ben has to leave early that day to check in with his parole officer.
Rufus is pleased to have the opportunity to spend some quality time with his son. He is also pleased to be out of the penthouse, as he is still finding the atmosphere around Lily fairly toxic.
It was both these considerations that lead Rufus to the idea he lays out for Dan over their infamous waffles. Spring break is coming up and Rufus proposes that they take a road trip together, an opportunity to bond not only as father and son, but as two grown men. (It would also be a convenient excuse to get away from the chaos-filled life of his much-married wife, for a bit.)
Dan looks a little taken aback by the suggestion.
"Uh, wow, a real Humphrey road trip, huh?" he deadpans.
Rufus nods enthusiastically. "That's right son. Just you and me and the open road. What do you say?"
Dan pauses nervously. "Um, you know normally Dad I would love to, but the thing is I kind of made plans with friends," he replies evasively.
"Really?" Rufus responds in surprise. "I never really saw you as the Spring Break, Girls Gone Wild beach party type," he elaborates, a note of query in his voice.
"I'm not," Dan shakes his head. "I was actually planning on going to France for the holiday."
"France?" Rufus furrows his brow.
"Well, yeah, I mean the opportunity came up to go and there really seemed no reason not to and you know I've always really wanted to go to France," Dan falters around defensively.
Rufus raises his eyebrows questioningly. "Actually, no I did not know that." A smile begins to pull at Rufus's lips. He can tell that there is something going on here that Dan is avoiding talking about, and his keen parental instincts tell him it probably has something to do with a girl.
"So you're going to France with friends," he continues encouragingly.
"Well, a friend," Dan explains self-consciously.
"Anyone I know?"
Dan sighs. "Uh, yeah, I'm actually going with Blair," he mutters resignedly.
"Blair Waldorf?" Rufus asks incredulously, eyes wide. "You're going to spend two weeks in a foreign country with a girl you can't stand?"
"Oh, she's really not that bad once you get to know her," Dan answers defensively. "We've been hanging out a lot lately, as a matter of fact." He grins sheepishly at his father "In fact, with Vanessa gone, she's sort of become my new best friend."
"I see," Rufus replies consideringly.
Dan looks down and blurts at the rest in a hurry. "Yeah, and she's going to France to spend some time with her father and see the Spring fashion shows, and she offered to put me up if I agreed to be on bag-carrying duty when she goes shopping, and I have a bit of money saved up for my airfares and that so it just seemed like a really good time to go..." he trailed off awkwardly.
Rufus pictured the girl with the elfin features who he knew as his step-daughter's best friend, daughter's nemesis and, until recently, his son's tormentor. When Dan had first described her to him four years ago as a '95-pound doe-eyed, bon-mots tossing, label-whoring package of girly evil' Rufus had noted that, despite his stated aversion to the girl, in depicting her Dan had sounded more intrigued than repulsed. And as Rufus had told him at the time, people like that usually had a reason for acting the way they did. Having got to know Blair, he was more certain than ever that that was true.
Rufus had also thought there might be a spark between the two a year later, despite Dan's protestations that such thinking was 'sick'. (Dan's objection had seemed just a little too emphatic to be totally believable.)
Rufus grinned broadly at his son. "Well, we can take a trip together another time. In the meantime, I think a dose of French culture might be just what you need."