They're nineteen when she runs away with a prince.
Off to France and the fairytale life she's always dreamed of. Standing in his kitchen the night of her departure, the ring sparking and priceless on her finger, she lets him in on her plan. It's hard to offer an unbiased opinion because this can't be real life, because this kind of thing doesn't actually happen.
It only takes a second to realize that she's Blair Waldorf, and if it was ever going to happen to anyone, it would be her.
Her eyes search his, but for what he doesn't know. Some kind of blessing? An acknowledgement that abandoning everyone and everything she knows is a completely acceptable act?
"I have to do this," she says softly. "I mean, I can't… Not."
He steps closer, a cautious hand placed on her shoulder, his touch and her acceptance of it something that hasn't changed.
"Does he make you happy?"
Eyes widen slightly, the thought that, despite everything that happened between them, he's the first to ask her such a thing. He's the only person who takes her feelings into account.
She twists the ring back and forth on her finger before answering: yes.
"Then nothing else matters."
The breath that falls from her lips is relief. Her hug hesitant at first, but she relaxes into him when his arms wrap around her shoulders.
"I think I might actually miss you," she says against his shoulder. "How pathetic is that?"
Blair is gone a week when he pays a visit to dad and Lily. Eric and Serena are there too, in some unplanned pseudo step family gathering that is as uncomfortable as it is awkward. Then waffles are made, and conversation springs forth and is actually held in some semblance of normalcy.
Later, he's washing dishes while everyone sits in front of the TV watching some documentary on the 90's music scene that happens to mention Lincoln Hawk, Serena approaches and offers to dry.
"Have you heard from Blair?" She asks without a trace of subtlety, her acceptance of the brief relationship between them, still bordering on incredulous. "I know you two had-"
"No," he interrupts, handing her a dish she wipes with a towel half-heartedly. He doesn't like lying to her, but would rather not rehash what went on between him and her best friend for the umpteenth time.
"I just," she starts, stops and puts the dish on the rack and stares at it. "She left. The biggest decision of her left and she took off without saying anything to anyone."
Dan squirts more soap onto the scrubber and keeps mum, taking small satisfaction in the fact that he appears to be the only one Blair made a point of saying goodbye to.
She's twenty when she discovers that the happily every after part is a lie.
Louis' family doesn't like her. Despite her being brought up in one of the most privileged and well to do neighborhoods in the world, one year of Ivy League education and fluent French, she's nothing but a commoner to them. A peasant. And worst of all, American.
He defends her honor of course, but it still stings, the fact that he has to. Suspicion and distrust of her love for him, her motivations for marriage despite him being to the one to find her, to ask her, constantly poking at her insecurities like a red hot needle.
Despite what she's spent her whole life believing, she is not sleeping beauty and yet, her eyes feel like they're finally opening.
Her face is everywhere.
Splashed across every single tabloid newspaper and magazine in the country. She naively thought that being one of Gossip Girl's favorite subjects for most of her adolescence would have prepared her for the mudslinging and rumors. But when an entire journalistic mob is screaming for personal details that no one has any business knowing, instead of a single entity hidden behind an anonymous internet, it's a whole different monster.
One she isn't sure she can handle.
She tries to keep her head up, tell herself that love truly conquers all, and it's worth the suffering because this life is everything she's ever wanted. Louis cares for her, treats her like royalty even if it's still technically untrue.
It's enough because it has to be.
Because she needs it to be.
He's twenty-one when he graduates from NYU.
Dad throws a barbecue at the loft and everyone he's ever known actually RSVP's, so the walls are packed with congratulations and well wishing. His newly acquired position at the New Yorker, a lowly research and copy editing job but a foot in the door, the talk and toast of the party.
Chelsea doesn't leave his side almost the entire time, and it's odd because she's never been one to cling, but in between and the handshakes and pats on the back he starts to notice the guilty look in her eye.
They'd been dating since the start of junior year, so he knows her well enough to ignore the denial that something is bothering her, but she insists and tells him to enjoy his moment.
He can barely eat after that.
She breaks up with him at the top of the stairs of the subway station. She lied about getting that job at EW, and doesn't know why. She does, however, have an offer from a movie studio out in California and took it.
Tears stream down her face, because she feels guilty, because she really loves him and was in denial about having to go. Dan doesn't know what to say, placing a hand upon her cheek, but knows he'd be a pretty big hypocrite if he begged her to stay.
He gets his second story published in the New Yorker after she's gone.
"People Always Leave" a tale that has the editor-in-chief promising to keep an eye out for him in the future.
She's twenty-two when she graduates from the American University of Paris.
After things with Louis had fallen apart, as they would predictably do, she retreated to her father's chateau for six months waiting for the mob of paparazzi interest in her to fade. She doesn't want to go back to New York and surprisingly, her father is ecstatic that she stays.
He puts in a good word with a friend of his in admissions, and she's accepted almost immediately. She works hard, harder than she ever had before, and it's so remarkably easy to accomplish her goals without the distraction of society living.
She breezes through her course work in record time, making up for the year and a half deferral princess debacle, without so much as a blink.
Daddy throws a soiree when she gets her diploma; mother flies in with Cyrus, and brings Serena along as a graduation present.
Their hug is more awkward than it should be.
They haven't seen each other in three years.
"I love Paris in the summer," Serena says, waving her arms around in a grand gesture, the coffee cup in her hand nearly spilling over.
Blair walks beside her, hands clutching at the strap of her bag, watching boats float listlessly along the Seine.
It's a strange feeling not knowing how to talk to her best friend all of a sudden. The time missed between them feeling like decades rather than a few short years. Serena stops to lean on the ledge of the bridge, absently sipping her coffee and following Blair's gaze to the boat.
"I'm proud of you, you know," she says.
Blair blinks at the statement.
"That you didn't run," Serena clarifies. "That you held your head high and stood your ground. Now look at you, college graduate. You have the world in your palm."
Something loosens inside, Blair suddenly feeling the need to hug the buxom blonde, and does so.
"How is everything back home?" she asks.
"Things are good," Serena replies. "Eric is at Columbia now. Mom and Rufus are still happy. Chuck is-"
"I didn't ask about Chuck," Blair interrupts, body going rigid again at the mere mention of his name.
They're quiet a moment, then Blair suddenly asks, "How is Humphrey?"
It's Serena's turn to balk, looking away and laughing softly to herself.
"Good," she replies. "He's a junior editor at the New Yorker."
"Oh?" Blair says, unable to keep the surprised tone from her voice. "That's nice."
He's twenty-three when he writes a best seller without really trying.
The Times says his voice is "evocative" and "fresh." Kirkus reviews gives it four stars, and the New Yorker boasts his accomplishment as homegrown talent.
Everyone he knows is shocked that the subject matter of a boy from the wrong side of town falling in love with an upper class debutante isn't an autobiographical retelling of the story of he and Serena.
Everyone except the girl herself, waving the book in his face with an exasperated yet knowing look, telling him she knew. Somehow, someway, she knew it was more than they ever said.
Dan says he doesn't know what she's talking about, and she only rolls her eyes and leaves a piece of paper with a phone number prefaced with the country code for France.
It takes a week for him to actually call.
The scrap piece of paper with the number taped casually to the edge of his computer monitor, mocking him for his cowardice every time he entertained the idea of dialing but didn't.
She picks up on the second ring, and the exasperated greeting in French gives him pause.
"Who is this?" comes out sharply, the tone of suspicion in her voice still familiar.
"It's nice to hear from you too," he says dryly.
"Humphrey?" A pause, then: "Who gave you this number?"
He can practically hear the rolling of her eyes.
"I hear you're in the magazine business too," He says, trying to hold back a smile. "Tell me every little thing."
They're twenty-four when they see each other again.
At Serena's wedding, sitting side by side at the bar, he with a gin and tonic, she with a flute of champagne, stem held lithely between her fingers.
"To the first of many," Dan jokes, raising his glass.
"Must you be so crass?" She replies, but concedes to the clinking of their glasses. "What do you know about this groom of hers? Is he going to treat her right?"
He takes a pull of his drink before answering.
"You were in the wedding party and don't know anything about the man your best friend is marrying?"
"I live in Paris," comes the retort as she folds her arms. "It's hard to keep tabs there. Okay?"
He throws his hands up in defense, before taking another drink.
"I hear Paris is lovely this time of year."
She lets her arms down.
"Paris is lovely any time of year," she replies. "But yes, spring is particularly ."
He smiles, one hand reaching out for hers and she doesn't shy away.
"I've missed you."
She turns her head so he can't see hers.
"Only you Humphrey," she starts, pauses to take a sip of champagne, "would take three-hundred and eighty-seven pages to say as much."
"You read it?"
"I didn't mind being thinly veiled."
Later, they're dancing in slow circles around the floor, and everyone's eyes are on the bride and groom so they aren't paid much attention.
"How's work?" He asks, eyes catching hers.
"Your attempt at small talk is noted."
He waits, she sighs.
"Hectic, stressful," she replies. "But I love it. You?"
The song ends, but they don't stop, simply waiting for the next one to start.
"I always thought you'd come back," he says, fingers circling the small of her back. "After everything."
"I thought about it," she admits.
"Something had to change," she says. "I had to-what does it matter?"
He doesn't answer, just spins her around and keeps dancing.
"Do you ever think about-"
"It was a long time ago."
"That's not an answer."
Neither is her kiss.
She's twenty-five when she returns to New York.
The transfer offer from Vogue is too good to pass up. Blog duties as always, but her own column is definitely the cherry on top.
Her mother is pleased upon the news, and Serena's ecstatic squeal over the phone is as good a reaction as she could hope to get. Dan, ever the precautionary bearer of her feelings, asks if it's what she really wants.
When she says that it is, his relieved laughter makes her smile.
They all pick her up from the airport: Her mother, Serena, and Dan. Humphrey even goes so far as to have a placard with Welcome Home Waldorf printed on it. It's welcoming hugs all around, but when Dan's turn comes up, any doubt she may have had about the decision quietly fades away.
He helps her move into the brownstone apartment she rented on Madison. All the little things the movers don't usually touch. He's unpacking her books and offering a color commentary on nearly every single one, and while she agrees with most of what he says, she fires off counterpoints because she can't let it be so easy.
Later, they're drinking tea and munching on Jordan almonds because they are the only consumable items she has at the moment. He's got one of her books resting in his lap, idly reading while the teacup cools in his hand.
"Let's get something straight," she says suddenly, causing his head to snap up. "I ran off to Europe for a prince, but I stayed there for me, just like I came back to New York for me. You were, in no way, a factor in my decision."
He laughs, but nods.
"That being said, it's a perfectly acceptable scenario if you want to kiss me."
He's twenty-six when his next book is released.
Just a collection of short stories, to appease his publisher while he works on his second book.
No one seems to question the affect she has on him, his writing prolific to the point where Dad teases him about her being his muse, but even after a year of dating Blair his family can't quite seem to understand it.
The relationship stays content and stable.
They tease, taunt, and bicker as much as they always had before.
The only difference is they couldn't be happier about it.
It's almost three in the morning when he wakes to see her leaning against the windowsill, watching it rain. His breath catches, the way a stray beam of light streaks across her face, pressed gently against the glass.
He has to leave in the morning, a book tour the last thing he wants, but his publisher wouldn't take no for an answer. No attempt was made to try and get her to come along, because he knows the chances that she would agree to sleep in a hotel bed at the Dallas airport Hilton, are slim to none.
A kiss pressed into her shoulder earns him a smile in the reflection of the glass.
"Marry me," he whispers against her skin.
She doesn't answer.
Her hand moves to find his.
"I heard your offer," she says softly. "I'll consider it."
They're twenty-seven when they marry.
On her father's yacht off the coast of Capri, a small and intimate gathering for immediate family only. She wears a dress designed by her mother, and he wears a tux hand picked by her.
They promise to have and to hold, to never hurt nor betray, to say forever and mean it.
It's the kind of fairytale she's always believed it. It's the kind of story he's always wanted to write.
Rich girls don't marry poor boys.
Except when they do.