Chapter Text
It starts on Henry's 16th birthday party.
While the gathering isn't as extravagant as her own Kiss on the Lips party had been many moons ago - the Waldorfs were finally back in New York and they were celebrating in style. Henry himself had made sure of that.
The guest list, triple checked as custom, was sent out with approval from Blair's imperious eldest. Despite the vast majority of her children's lives being spent in France, Blair was pleasantly surprised to see that it was no great hindrance to the amount of attendants welcoming them back to the city. Months spent at the upper class summer camps of Manhattan resulted in both Henry and Tilly knowing many a familiar face in the halls of St Jude and Constance Billard in advance of their upcoming attendance to the schools in the fall.
That was not even to mention Blair's own frequent visits back to New York, as her work required it given that she was now the most iconic editor-in-chief to the long-running fashion magazine, W. Yes, after the disastrous results of her first two marriages, Blair Waldorf had risen from the ashes and emerged victorious.
Still, frequenting the island of Manhattan wasn't the same as living in it.
That was something Blair just couldn't bring herself to do.
Not after Chuck.
And certainly not with her young children. It was only after Matilda's birth that she finally closed her heart to her second husband forever. Chuck had been negligent, his attention waning and his affections mercurial after the first year of Henry's young life. He'd travel for work frequently, leaving Blair to attend to the maintenance of their hotels and businesses in New York by herself, whilst the months he spent away from the city stretched out longer and longer. When he missed the birth of their daughter, it wasn't so much the final straw as just another drop in the bucket. Except the bucket finally overflowed.
The divorce lasted a decade.
Chuck and his lawyers turned the court into a circus of mayhem and manipulation, making Blair ever more grateful and steadfast in her decision to cut all ties and move the children with her to France. Their grandparents were there, and they had always been welcome.
Cyrus and Eleanor took them in easily, her mother for once supporting Blair without judgement, as her grandchildren grew in the arrondissements of Paris. In the south of France, Harold and Roman were just as welcoming to Blair and her children, their sunny dispositions doing wonders for the single mother as she rediscovered who she was without the influence of her ex husband. Blair thrived in the years following her separation from Chuck, and eventually she accepted the offer from W to be their official dictator of taste.
Still, it was only a few months earlier that the divorce was finalized.
And only a few days after that when the news surfaced that Chuck had passed on, from heartbreak if not high blood pressure, the tabloids speculated.
Blair and her children had gracefully refrained from celebrating, though Henry was most insistent (from his lingering bitterness at still carrying their father's last name while his younger sister had been lucky enough to have been born Matilda Waldorf, Tilly herself speculated). It was only coincidence that Cyrus brought a veritable tower of Ladurée macarons home that night.
It almost matched the height of the macaron tower Eleanor had brought home only a week before, when the divorce was finalized.
Thus, it was a few months later that Blair Waldorf and her children, Henry and Tilly, were finally moving back to New York. Blair's assistant, second in command, and (basically) her right hand; Stash, had found them a gorgeous light-flooded penthouse on the 95th street at Carnegie Hill. It was there that she finally felt safe enough to discard Chuck Bass and all the regrettable memories he brought as baggage.
Unfortunately, not everything from her past was so easily forgotten.
"Maman." Henry swept through the guests milling about on the marble floors of their new home, his excitement subtle even as he presented Blair with a twin copy of her childhood best friend (albeit a much relaxed version). "This is Bernadette Humphrey. Birdie, meet ma mère."
"How wonderful to see you again, Bernadette." Blair replied gracefully, for she would be hard-pressed to refer to anybody as 'Birdie', child of Serena's or not.
"Birdie, please Ms. Waldorf. I think anyone who was present at the hospital during my birth deserves at least that honour." The young blonde corrects her with an easy laugh. It's so reminiscent of her old best friend, Blair has to blink rapidly to clear away the fog of nostalgia.
"And how is your mother?" She asks with open curiosity. The last time she saw Serena, her best friend had been shinier than ever, taking over LA one Hollywood blockbuster at a time. As the 15-year old responds, both she and Henry are regaled with tales of summer on the West Coast.
Carefully, Blair does not ask after the child's father.
Queller's been up his ass about the new curriculum since before the school year even started.
For such an old lady, she was truly formidable, and Dan would've been more curious at the catalyst which had lit a fire under her if he wasn't suddenly so busy with trying to keep up with her demands. Usually, the Headmistress trusted him enough on his own, trusted his judgement in engineering his own classes accordingly, not running him through his class plans and performance measures like she was worried he'd forget it in the morning commute to the joint schools.
Luckily, he didn't have to wonder long, as the reason came in the form of two recognisable new students. Henry Bass and Matilda Waldorf, though the latter seemed to prefer 'Tilly', if his youngest was to be believed (Rory rarely made new friends in equal pace to her older sister, so when she did it was a novelty each time) while the former seemed to avoid his surname altogether.
They were good students of course, they took after their mother.
Dan spent a tense few weeks at the start of the semester waiting for the other shoe to drop, for Blair Waldorf to storm into his classroom just like she used to, blazing with self-righteous fury right into the Brooklyn Humphrey loft. She doesn't though, has no reason to really (though it's not as if that's ever stopped her before, and was he truly so fucked up now that he actually missed it?) so Dan eventually eases back into the routine of New York in autumn and the school year with all its usual troubles.
He's not unhappy with where life has taken him, has almost no regrets in fact, now that he's decades away from when he first stepped into the world of the Upper East side.
He has two wonderful daughters, both blonde clones of their mother, and while one certainly takes after Serena more in spirit whilst the other has taken on his own pessimistic disposition from his teen years (he really doesn't know where Rory gets it, movie nights are uphill battles most of the time with his youngest screaming for Koyaanisqatsi while Birdie holds out their old DVD containing The Sisterhood of the Traveling Pants like an indignant war mast) Dan can still say with surety that he's proud of them both.
Even the custody arrangements weren't too bad.
Not long after Rory was born, when Birdie had just turned two, he and Serena had finally looked at each other and called it quits for good.
It was somewhat anticlimactic in the end, especially after all of their drama and the back-and-forth fights with scandals recorded on Gossip Girl for prosperity. They just got tired of it, and they had became disillusioned with the idea of spending the rest of their lives together soon after.
The divorce was quick, amicable, and more of a celebration than it had any right to be considering their history.
It was no surprise then, that Dan and Serena remained friends. Hell, even Nate was still his best friend, despite the fact that the guy was now making his ex-wife happy, producing her dreams and far-fetched fantasies into blockbuster movies for the masses to enjoy and worship them for. They were golden, the power couple of Hollywood, and Dan couldn't even bring himself to hate them for it. Especially not when his daughters were so delighted, the two teenaged girls were all too happy to split their summers between weeks in the Hamptons with Rufus and Lily (they'd initially moved there in the aftermath of the falsified affidavit and everything that happened with Ben and Serena, but eventually they liked it enough to stay) and weeks running through the streets of LA with their mother and stepfather.
So yeah, life was pretty good.
Dan certainly didn't feel like he could complain. But still. It was somewhat lacklustre. What felt like a million years ago now, he had once been a writer, a successful one even. But after marriage, and the whirlwind of bringing two of the most perfect little girls into the world, Dan had somehow left his old hobby behind.
Still, even as a divorcé Dan was receiving kudos for his work on Inside, every few years or so.
One such review came to him unexpectedly towards the later end of the first semester.
"So, your dad wrote this when he was our age?" Matilda Waldorf's incredulity was clear in the courtyard connecting Constance Billard with St Jude's.
"He started it when he was our age, yeah." Rory Humphrey replied factually, her expression pleased as she took in the awe in her friend's eyes. "Here, you can have a signed copy, we have a bajillion at home-"
Dan was about to step in at that point, to say that the number was really closer to the few hundred thousand mark, not quite as pathetic as a hoarder's bajillion when a new voice spoke and his breath was knocked straight out of his chest.
"That's alright thank you, Rory." Blair Waldorf smiled at his daughter, gently handing Inside back to the 13-year old before turning back to her own daughter. "We have our own signed copy at home Tilly, I think your brother's just about finished with it." And sure enough, Henry Bass stood just behind his mother, his expression unimpressed.
"It was a hard read honestly, with Dylan and Claire being such a slowburn." The 16-year old brunet complained, his eyes widening slightly when they caught on Dan. "Sorry, sir."
But Dan just waved off his apology, he was still too caught up with the boy's mother to really take offence. "Blair..." he greeted her softly. "I didn't know you were coming to pick up the kids." He'd heard about her and Chuck's divorce of course, the same as everyone else on the planet who'd been caught up with the decade long legal proceedings, and he'd heard about Chuck's death shortly after, feeling little more than relief on her behalf.
"I had some time today, my assistant took over for me at the office." She replied with an offhand explanation. Their children looked between them with curiosity, as even Birdie had joined them at this point.
"Wait, you two know each other?" The 15-year old blonde asked.
"Yes," Blair smiled and he felt his own lips twitch without his intention. "We were friends."
"Not friends." Dan couldn't help but correct her, his tone teasing, willing her to remember. Of course, she did.
"Not friends, then." Blair agreed with that same secret smile, and he could almost swear he felt the years between them melt away. "Are you here to pick up your children too, Humphrey?"
"I'm the English teacher here." Dan told her. "Head of the Department, actually." Even now, he couldn't help but try to impress her.
"Well done, you." Blair replied, meaning it. "I'm glad to hear my children are in good hands."
That was as much a parting adieu as it was a compliment, and soon enough the Waldorf contingent were tucking themselves out of the cold and into the warmth of their town car. Dan watched on, ignoring the still curious glances of his own daughters in favour of tracking the cameo of Blair's face in the shadowed window of the limo. She had aged gracefully, and looking at her was still simultaneously a blessing and a curse.
It still broke his heart.