I've shipped Dair and Chair simultaneously since pretty much the beginning of the series, not caring which guy she ended up with, and enjoying watching each relationship blossom.
But starting with the whole Jack/Blair/hotel mess, I was so turned off by Chair that I started to decide maybe she really was better off with Dan. And then I jumped off the Chair ship for good when Chuck broke the glass in his apartment and it cut Blair's cheek. The writers have continued to make Chuck such an abusive, manipulative, irredeemable character that I can't imagine him making Blair happy ever again.
And the way the Dair relationship has played out these past two seasons has been just magical to watch. So I'm firmly in Dair's camp now.
I know that in all likelihood, Chair is endgame. So I decided I wanted to write a fluffy, happy, Dair-together-forever fic so that in my own fanon, at least, they'll live happily ever after.
Without further ado, here's my silly, sappy take on Dan and Blair's engagement.
Enjoy!
-Brandi
Disclaimer: I don't own Gossip Girl or any of its characters. I'm definitely not making a profit from this and I will continue to support the show by watching it legally on Hulu.
Worth the Wait
They've been together three years. In that time, they've both managed to graduate from college. Blair's now an assistant editor at Vogue and Monarch of Manhattan did so well that Dan's writing full time, churning out bestseller after bestseller.
They've talked about marriage on and off for a while. Dan uses his latest royalty check to buy her a ring, and he's been hiding it from her for over a month, waiting for the perfect opportunity to propose.
But it's the driest summer Manhattan's ever seen. If it doesn't rain soon he's tempted to throw his plan out the window and get down on one knee the next time he sees her.
It doesn't help that she's a very impatient person.
"Humphrey, will you hurry up and propose already?" she asks one morning as they're making breakfast together in their Upper West Side apartment. (It's not the UES, but they can't afford that on their own, and at least it's not Brooklyn, where Blair swore she could never live, no matter how much she loved him. This is the perfect compromise.)
She's using his last name, which means she could be anywhere on the spectrum of mildly annoyed to royally pissed off. Her tone suggests moderate aggravation.
"Did you or did you not tell me you wanted it to be a surprise?" Dan asks.
"Well, I didn't think you'd take so long to do it! If you don't soon I'm going to have to do it myself."
"Being proposed to wouldn't be so bad. I think I'd like that," Dan says as she glares daggers at him.
He smiles, and this frustrates her even more—she hates not being in on the secret.
"It's coming. I promise."
"It better be," she huffs.
It takes two more days before there's even an overcast-enough sky to suggest rain. They haven't said another word about getting married, and while he knows she's not really mad at him, she is wondering what's taking so long.
He gets his lucky break that Friday morning. They wake up to a downpour, and as soon as Blair leaves for work he puts his plan into action.
He calls Dorota first. "It's time," he says, and he can practically hear her grinning through the phone. "You know what to do."
He heads to Prada, where he stashed his costume and the props months ago. He knows Blair's not a fan of DIY projects. But he has one chance to propose, and he's been thinking about it for years, pretty much since the first time they watched the movie together. So he can't back out now.
He tells his father today's the day, and Rufus and Lily round up Eleanor and Cyrus. No one is quite sure exactly what time Dorota will be able to get Blair away from work, and how much of a fight she'll put up about Dorota blindfolding her.
They spend the morning sitting and waiting at the penthouse, Dan picturing the plan in his head over and over again, willing things to go smoothly. The rain is still pouring down.
At noon, Dorota texts him. Getting in cab with Miss Blair. Blindfold on. See you in twenty.
Dan herds his parents and his future in-laws into the waiting town car and they head to the meeting place. He hadn't planned for their parents to get in on it, but Eleanor heard him discussing the plan with Dorota awhile back, and she insisted she be there to take pictures. So he decided he may as well invite his dad and Lily along for the actual event, and then they'll celebrate with their friends at dinner later. As much as he wanted this to be something between just him and Blair, it's nice to have their moral support.
They arrive at the alley, the driver parks nearby, and Dan runs outside to set things up. He insists on going out into the blinding rain alone; no point in all of them getting soaked. He's been stealing flattened cardboard boxes from his publisher's recycling bins. He bends them into shape now, thankful that his costume is actually protecting him (all but his head) from the rain. He can't wait to see Blair's face when she finds out what she's wearing. Dorota had to put it on her after she was blindfolded, so she has no idea what it is. He places the last prop inside one of the boxes, and it's already soaking wet. He hopes it won't get too ruined.
His cheering section gets out of the town car then, holding umbrellas above their heads and huddling in a nearby corner so they can see the action, but Blair won't see them. They already have their cameras ready, and Dan feels a wave of affection for his family. If all goes well, he might actually enjoy himself. That is, if he can keep his breakfast down, because his nerves are shot.
Dan heads to the nearest overhang and tries as best he can to stay dry while he waits.
A few minutes later, a yellow cab pulls up and Dorota gets out, pushing open an umbrella and guiding a still-blindfolded Blair out onto the pavement.
Dan steps out from under the overhang and walks towards them. "Thanks, Dorota."
"Dan?" Blair asks, smile playing across her lips. He knows she's probably already figured out that she's being proposed to, but he also knows she would never guess what she's going to open her eyes and see.
He doesn't answer her, and Dorota pulls off the blindfold, pushing her out into the rain. Blair blinks, taking in her surroundings. They're standing at the entrance to an alley a few streets over from the Met, so it's familiar territory.
She looks at Dan for answers, but all Dan says is, "Here, Cat! Cat!" He looks out into the alley, fighting the urge to watch Blair. When he does sneak a peek, he sees her face light up. She glances down at her cream-colored trenchcoat and then looks at the similar one he's wearing. He watches her expression click over to understanding: They're doing the last scene of Breakfast at Tiffany's. She beams at him, and Dan repeats his line.
Blair comes closer to him, the rain streaking her face so she can barely see. "Where's the cat?" she asks uncertainly. He nods, water splashing down his chin. She says it again, this time in an Audrey voice, "Where's the cat?"
"I don't know," Dan says, still quoting the movie. Blair stands there, hesitating.
"Go look!" Dan stage whispers, and he hears chuckles from the peanut gallery. Blair doesn't take her eyes off of him to notice their parents and Dorota.
She darts into the alley, giggling like mad. She looks into the cardboard boxes, which are so soggy they're falling apart, and when she pulls a stuffed cat out of one, she whoops in triumph.
He stares through the rain at her, willing her to see the box tied around the cat's neck. Blair does notice it, and as she opens the velvet box, Dan drops onto one knee and holds out his hand.
As soon as she realizes the cat's ring box is empty, she looks up—and sees Dan, kneeling a few yards away with something glinting in his palm.
She runs toward him, still clutching the stuffed cat and now a little breathless. He's a little breathless, too.
"Marry me?" Is all he can get out, and she's already on her knees, hugging him, obviously not caring that her tights are now ragged and soaked.
"Yes! Yes!" she shouts, and for the first time, she notices their parents. "Can somebody bring us an umbrella? I can't see the ring!"
Dorota's closest so she rushes over, holding her umbrella over the kneeling couple.
Now that they're shielded from the weather somewhat, Dan holds up the ring. Her eyes widen. "It's beautiful."
He sighs, relieved that she loves it, and slips it onto her left hand. They embrace again, and their families cheer when they kiss.
When they break apart, she smacks his chest. "You are a crazy person!"
He helps her stand up, and they huddle next to Dorota. "Now you know why I waited so long. I needed to set the mood." He gestures to the rain, and she laughs and holds out her hand, raindrops falling so hard they're bouncing off of her palm. "Worth the wait?" he asks with a smile.
She nods so hard her rain-matted hair bounces. "I love you."
He whispers it back, and by then their parents are surrounding them, exclaiming over the ring and hugging them both, their umbrellas bumping together as they squish in to keep dry.
Dan meets Blair's eyes through their little celebratory cluster, and she's crying. His eyes are starting to water too and he figures he may as well let it out. After all, they've been waiting for this for a really, really long time. And from the way Blair's looking at him, it couldn't have gone more perfectly.
