Post S5 finale. AU after S6. Mostly future-fic with some back story, and flashbacks. Blair has a long way to go in self discovery in my opinion, she was just out right crazy in S5, it's the only way I can justify all of her actions. So Dan and Blair haven't seen each other in almost 20 years.
Prologue:
When you've just gotten your heart broken, you can't focus on anything other than the pain that seems to radiate out of every pore in your body. Each morning you wake up after another night filled with nightmares, only to feel the ever present ache again. And you can't imagine the day it will ever go away.
But that is what time does for us. It doesn't heal the wounds, or make you forget entirely, it teaches us how to deal with loss. It's a lot like trying to lose weight, you can't see the changes from day to day but if you look back to where you started, you can't believe how far you've come. And if you do it right the past becomes muddled and you can't seem to remember all the details. But if you do it wrong, you gain it back and you carry it with you wherever you go.
In a lot of ways our mind is programmed to stop needing someone after so long of not being in contact with them. Most people who are granted the chance, to find closure, yell, scream, cry, and be heard, have it the easiest. Because after it's all said and done, you begin to replace old experiences with new ones, and you have new losses and new pain to deal with, covering up old wounds until they are barely recognizable.
However, some people don't have it so easy, our body is also programmed to remember that last, all consuming pain that changes our lives, when we don't allow ourselves anything to replace it with. When you aren't given the chance to grieve, or to repent, or to find closure, you become hard, you lose your full capacity to feel things so you're mind holds on to the last time you allowed yourself to feel completely. The result is, you don't grow, or change, or experience new things. You become bitter, hollow, and insensitive.
That was the excuse Dan gave himself when he wrote the sequel to Inside. He felt betrayed and full of anger. He could also hear bitterness, resentment, and downright hatred knocking on his door. He knew if he didn't get it out, everything he ever wanted to say, needed to say, he would hold on to it and it would utterly destroy him to the point where he may never be able to recover.
He poured every thought and feeling he ever had about the Upper East Side including Blair Waldorf and Serena Van Der Woodsen, into his novel, and then he waited. It took awhile, he had to take it day by day. But time worked in his favor, and he could feel himself start to open up again.
After his summer in Rome, he decided to stay the next year to finish his degree. While studying abroad, he had a few rebounds with women whom he could barely pronounce their name, let alone have a full conversation with. He managed to screen most of the calls from journalists wanting to interview him about his latest novel, the fact that he remained so elusive after it's debut made people even crazier about it. He had managed to read one article theorizing Dan Humphrey was in fact dead, taken out by the angry elitist families he had insulted. He laughed at that one.
Nate tried to contact him once, probably not to thank him for putting him in the book this time, and Dan couldn't bring himself to return the call. He never heard from Blair or Serena. A month after the book, Dan caught a glimpse of an American tabloid and in the bottom right corner is where he found out about Chuck and Blair's engagement.
After finishing his bachelors, he applied to the masters program at Yale and with the sales from his two previous books, and a generous scholarship, his money problems were a thing of the past.
He met Cassandra Davenport, his first month at Yale, she was a senior studying film. Her father, Dillinger Davenport, was a billionaire responsible for huge conglomerates around the world, an old money family that dated back to the founding of the city Davenport, in which Yale is so closely associated. He made Bart Bass look like a poor pauper. Her families' social circle was the epitome of pretentiousness. Dan had considered himself a slight snob previously, but this was nothing compared to the supercilious laughter that surrounded him at every dinner. Upper East Side elites couldn't hold a candle to that of the old money families' of Connecticut.
Dan found Cassandra to be warm and as passionate about film as he was about writing. In a way, she reminded him a little of both Blair and Vanessa. While she liked the finer things in life, she was also down to Earth and cared about other peoples happiness just as much as her own. Cassandra was the spitting image of her mother, Vera, with wild light brown hair with natural gold highlights, that fell down her back in curls. She had bright blue eyes that turned green depending on her mood, and curves that made every guy turn back for a second look. He couldn't stop himself from comparing her again to his past loves, she lit up a room like Serena, but she controlled it, like Blair.
Dan found his first impression of the Davenports' wasn't entirely accurate. They had a certain reputation to uphold but behind closed doors they were just as bit as warm as Cassandra. They were a tight knit family, they played games like Apples to Apples and had dinner together at least thrice a month. Her two older brothers, Jeffrey and Piers, worked with Dillinger, and had begun families' of their own. After the perfunctory big brother speech, they gave him a beer, and teased him about his lack of athleticism. Her father was regular news, usually in the press about his ruthless business practices, but somehow they managed to keep the important things private, as if they all enjoyed keeping up the pretenses if it meant having this secret, and Dan fell in love with Cassandra even more.
Dan didn't mind the public dinners or galas after that, as they spent many nights rolling their eyes and sniggering with laughter as they heard the names of Philip Glass, Rachmaninov, and Wordsworth mentioned in every conversation. They couldn't pass a group of ladies without someone mentioning "have you heard the news, Sally Dirven's husband has taken to the bottle again." It was always "news", never gossip.
They made these obligations into private jokes of who could sound more like a prat. Cassandra always won having grown up around it. She could have a twenty minute conversation about a glass of wine, spewing out mounds of bullshit without anyone ever calling her on it.
"A sublet hint of backne, stimulating the palate without overpowering the excessively large fupa undertones."
She had a way of raising her eyebrows anytime anyone looked at her peculiarly as if they would spontaneously combust for questioning her and they quickly scurried away.
Dan gave her a run for her money as he would ask every host about the price of his house, feigning obsessive interest in the property market, and going on about the desirable areas in which he planned to buy, as soon as he was done with school and how he was so disappointed in the lack of style of the dormitories. He added words like vastly and proverbial to every sentence.
Sometimes they would catch a disapproving look from Dillinger or Vera, and then the twinkle of their eye would reveal they were laughing on the inside. For the first time in a long time, Dan pictured what the rest of his life would be like with a girl, and with Cassandra, he liked what he saw.
Despite the press and the prestige that surrounded Cassandra's family, she managed to find a group of close friends whom she could drink beer, eat pizza, and still talk about literature, film, and music, without mentioning Shakespeare or Russian classical. Since Cassandra had been there for four years, their group was private and exclusive, and Dan fit a hole they hadn't realized they had until he was there. They were the first real friends Dan had made since Vanessa, they made him feel like he had known them his entire life.
Dan started watching football, adorned in a Yale sweatshirt, tailgating before every game. He was a staff columnist at the Yale Daily News. His friends introduced him to all of the Yale traditions, and three months into the school year he abandoned his dorm and moved into the spare bedroom in an old Victorian style house on Old Campus, that all of the guys shared. He was busy all the time, and he loved every minute of it.
He shied away from telling people he was a published author, but people found out and questioned him about Inside and Exiled every where he went. It was the subject of his and Cassandra's first, second, and third fight. They spent a lot of late nights discussing Gossip Girl, and the destruction that seemed to follow anyone who got mixed up in the Upper East Side who didn't belong there. She was fascinated and appalled by his stories, refusing to believe how much of his novels weren't actually fiction.
The first fight they had was because she took Blair's side over his. She called him a judgmental prick for using Blair's real life tragedies for his personal gain. She didn't understand how he could write such beautiful things about her and a year later, completely degrade her. She thought it was obvious anyone who suffers a miscarriage is allowed a free pass, that any girl in their right mind would be utterly confused. She questioned his morals and his definition of love because surely he didn't know the real meaning if he could publicize her dirty laundry so abhorrently just because she had left him without a goodbye.
He told her his reason for writing it, how often Blair had reassured him that he had nothing to worry about, and he refused to admit he was wrong. She took it as a sign that if he still felt that strongly about it than he must not be over her. That ignited fight number two.
When she suggested he write her an apology, the third fight was the worst. He tried to reason with her by telling her Blair probably hadn't even read the book, she used him, didn't care about him, and besides it had been over a year. She told him that it wasn't the point, and not to speak to her again. He was distraught and confused for two days until she showed up at his door at two am, tear stained cheeks. He hoped it was the last conversation they would ever have about Blair. Without any sleep, they walked to the nearest blue postage box, and sent the letter.
Rufus and Jenny had visited over Thanksgiving, and took an immediate liking to Cassandra. Christmas came and went, Dan spent a week in Switzerland, skiing with the Davenports'. He and Cassandra had never been better. The next few months followed in similar fashion.
Rufus and Lily got remarried around Easter. It was a quiet ceremony, in upstate New York. After a very confusing process of helping Chuck win back the Empire, Lily divorced Bart, and spent the rest of the time trying to prove her love to Rufus. They had been back together for almost six months. Dan tried to keep his disapproval from showing but it wasn't until he saw his long lost family gathered in front of him that he finally let it go.
He hugged Eric until he couldn't breathe. And he was overtaken with relief when Serena ran to give him a hug, forgiving all the history between them in that moment. Nate was at her side, silent and cautious. Dan held out his arms as Nate laughed and clapped him on the back. Dan never let go of Cassandra's hand for more than a second. She and Serena connected immediately, as expected and the entire night went better than okay, it was incredibly drama free for a Rhodes-Van Der Woodsen- Humphrey affair. Chuck and Blair were suspiciously absent. Dan and Cassandra returned to New Haven, more in love than ever.
In May it had been almost two years exactly since he had left the Upper East Side, and on the day of graduation, Dan asked Cassandra to be his wife, and when she accepted Dan could not be happier.
Present:
Seventeen years later, and if you were to ask Dan Humphrey about the time Blair Waldorf broke his heart back when he was twenty one, he would have a hard time remembering the who, what, where, when, and why of it all. He'd be lying if he said he never thought of her, he's seen her name in magazines, heard it mentioned on t.v., and he thought he saw her once in a crowd. He wonders if she got her wish, to be happy. But apart from those few moments, he hasn't felt the need to reminisce over their turbulent years spent being enemies, then friends, then lovers, ever.
That was until, he ended up back in New York City of all places, a single father, and where better to send his children than Constance Billard School for Girls and St. Jude's School for Boys.
Thanks for reading! I know this chapter was a lot of back history, the next chapter probably will be too explaining how Dan got to this point in his life. Eventual back history for Blair. Eventual Blair and Dan interaction because I do love them.