This is my first completed multiple chapter fic (yes it is completed). I'm very proud of this, so just a few notes. I will be posting a chapter of this fic once a week, probably on Thursdays like this chapter was posted. There are five chapters total. The first four chapters take situations from the show where Chuck and Blair could have ended up with different people and I just chose to elaborate on them. This was seriously meant to be a oneshot, but I word vomited and ended up with this monster of a fic.

This first chapter is set in late Season two and involves Nate/Blair and Chuck/Vanessa.



It happens so suddenly, she doesn't see it coming.

She spends so much time entertaining juvenile thoughts of her first love, she doesn't see it coming. Not until he walks into the Jenny Humphrey's birthday party with her. They stare at each other; his eyes are taken aback and hurt. And for a second she almost feels bad for standing in between Nate's legs, her hands wrapped around his neck.

That is until Vanessa wraps her hand around Chuck's neck and yanks him towards her.

She backs away from Nate and runs into Serena's room because she can't contemplate a world where Chuck Bass is with someone else, much less a harlot from Brooklyn.

There's a voice in her head that sounds suspiciously like Serena that snarls at her that it's not fair for her to move on and expect Chuck to sit on the sidelines heartbroken.

(But doesn't he deserve that? To feel just a bit of pain after everything he's put her through.)

Nate comes knocking on the door first, and she's so surprised, that she almost opens the door just to assure herself that it really is him. He gives up easily when she calls through the crack in the doorway that she really doesn't want to talk to anyone right now.

Chuck is more persistent. "Can we talk about this, Waldorf?" He asks repeatedly. And she tosses back barbs through the keyhole because Chuck Bass doesn't do talking. And the last thing she wants to with him is talk.

She's almost waiting for the innuendo laced line to be tossed back at her, but he just sighs heavily. "I won't do this anymore," he says, almost sternly. "We spent too much time this year not saying the right things to each other, I won't play that game anymore. Come to me when you're ready to grow up, Waldorf."

And then he leaves too, and she's alone.

She suddenly doesn't want that anymore.


Nate ends up making the grand gesture she's always wanted him to make. So she picks him.

(It's an easy choice really. He's here, he's trying, and he's easy. And he's not Chuck Bass.)

She texts Chuck right before the Gossip Girl blast comes out.

I'm done talking. I'm done.


They go to prom together, and it's a strange version of perfect.

Her dress is ruined by the dry cleaners. And her corsage goes missing. Nate's limo reservation is erased. And she thinks for one awful moment that she's going to lose Prom Queen to Nelly Yuki because Chuck Bass is a vengeful asshole.

But there's a replacement dress that comes straight out of her scrapbook, and it looks better without the corsage. There's a carriage waiting to take them to prom. She wins Prom Queen to everyone's surprise. And at the end of the night, Serena hands her the key to the Palace suite.

It's all too perfect, and it falls apart suddenly.

When she calls her Daddy to thank him for the dress, he tells her he's sorry that he forgot about her Prom, but he didn't send her the dress. She goes to Nate to thank him for the carriage ride (and for thinking on his feet), but he is as clueless as she is. She finds out from Jenny Humphrey that her minions were plotting against her and Chuck stuffed the ballot box so that she won. And Serena caves quickly when Blair asks her where she got the key.

She almost wants to go to Chuck and thank him and tell him that she loves him.

But then she remembers that he showed up to prom with Vanessa on his arm, and she stops.


She spends the summer apartment shopping with Nate.

She refuses to live in the place he found for them. He's upset about that, but he acquiesces because she agrees to move in with him.

(Sometimes she wonders if Chuck would have found the perfect place for them all on his own, or would he have just handed the reins to her, knowing she would only be happy if she picked the place.

He always understood her need to be control.)

She finds out halfway through the summer from Serena that Chuck is spending the summer backpacking through Europe with Vanessa and she gags. She proceeds to spend the afternoon afterwards scrolling through all the Chuck Bass Gossip Girl posts she had been steadily avoiding, tracking his progress throughout Europe.

She stops at a photo of him kissing Vanessa outside a café in Italy, and she feels sick to her stomach.

He's supposed to be miserable without her, he's supposed to be trying to win her back.

Not this. Never this.


She suffers through a year at NYU.

Vanessa is instantly popular. She's artsy and kind and everything Blair isn't. And Blair is determined to make sure that the Brooklynite doesn't get the Freshmen toast, because Vanessa cannot have everything. Not NYU, Chuck, and the toast.

She schemes and manipulates. And it almost works. But in the end, it backfires.

She watches from the back as Vanessa smiles serenely at the crowd, and Chuck sits up in the front row smiling proudly up at her.

She drops out of NYU after that.


Anne Archibald offers her the position of the face of her organization, Girls Inc. And she feels like something is finally going according to plan.

Nate finally decides on Journalism as a major at Columbia, and he's already got an internship lined up at The Spectator. She's taking charge of a major philanthropic organization and they're finally fitting into the roles she always thought they would fill. She the socialite wife, him the working husband.

But something is wrong, something is missing.

She's bored.

The magic of being chosen by Anne Archibald wears off quickly. Nate becomes occupied with his own thing, and she spends most of her days in their apartment alone, waiting for some new party or event or a new Gossip Girl blast about her friends at college.

She drifts away from Serena, burying herself in new friends, society wives, like her. Serena leaves for Brown and emails her regularly, then infrequently, then never.

It occurs to her later on that she didn't just lose Chuck, she lost Serena too. She lost two friends.


She marries Nate just after his graduation.

She wears custom Vera Wang, and he stands underneath the alter with a slightly constipated look. Her eyes drift to Chuck only when the Priest asks if she wants to marry Nate.

He looks back at her with lost eyes, asking her the same question she's been thinking.

How did we get here?

She says, "I do." And Chuck's eyes leave hers and drift towards Vanessa sitting in the crowd.


She finds out she's pregnant three months later, when Chuck Bass places a ring on Vanessa Abrams finger.

She feels a sick swirling in her stomach that isn't morning sickness as she watches them kiss chastely at their engagement party as a sick thought enters her head.

That should be me.

Nate's arm curls around her waist, blissfully oblivious as always. "They look good together."

She shoots him a look; he always said the wrong thing.


Despite her feelings about Chuck, she always tired to make her marriage work. Not just for external appearances, but because she was not a complete masochist, and she genuinely wanted to be happy with Nate.

She knows that doesn't matter to Nate, because he's still hung up on a blonde that she refuses to let him talk about, because it hurts too much.

It doesn't matter whether he talks to her about it or not, because in the end, she finds him screwing Serena Van der Woodsen in his office, where he's supposed to be working.

He has the decency to look ashamed as she stares at their entwined bodies coldly.

"Blair," he begins, unsure of what to say.

"We'll speak about this at home," she appraises the both of them, before turning around stalking out.


He meets her alone at home.

"I thought your whore would be with you," she says ruefully.

"Blair," he pleads with her, "She's your best friend."

"Was," she corrects him. "How long as this thing between the two you been going on?"

"Since we have been married," he whispers.

She inhales sharply, "God, Nate," she almost whimpers.

"Blair, please," he takes a few steps towards her, stopping when she holds up both her hands to prevent him from getting any closer to her. "We weren't happy together. Not even a little bit. I kept trying to fool myself into believing that we loved each other, but that day," he trails off, "we got married and it feels like the worst day of my life."

She winces.

"Things with Serena," he looks anywhere but her, "I didn't mean for them to happen, but they did, and she makes me happy. I know it's not right."

"It's not about your happiness, Archibald," she snaps at him, "We're about to have a child together."

"I know," he closes her eyes, "And that's part of the problem."

She takes a step back, "What?"

"I was going to divorce you that night. I owed Serena more than that. And I owed you more. But you said you were pregnant, and I couldn't just leave you like that." He rubs a hand over his face tiredly, "And then Grandfather found out about the divorce and he was furious. We had a discussion, and he made some valid points."

"You're not making any sense," she snaps at him finally, losing her patience.

"Grandfather thinks it is a good idea to remain married to each other," he says carefully, "despite any feelings we might have otherwise."

"Like hell," she snarls. She won't stay married to him. She refuses to. William Van der Bilt may be able to intimidate Nate, but he would never control her.

"Blair," he pleads, "we need each other. In a few years I might be running for Mayor, and I need a respectable wife that will play well with voters."

"Not a society it girl that shows all on magazine covers," she spits back. "But too bad, you've already chosen her."

"You need me too," he says, his voice taking on an edge. "You've relied on my name to join all your little boards and groups. If we get divorced, then what will you have."

"You forget that I'm a Waldorf, that name carries weight too, Archibald. Don't you forget that."

"I know," he backs down almost instantly. "Look Blair, I'm just trying to make the best of our situation. We're both stuck together, might as well try to be happy despite that."

She remains silent for a moment. "Are you going to still see her?" She asks finally.

"Yes," he answers almost immediately. "We've talked, and she understands." He swallows heavily, "I don't expect you to be faithful to me either, just discrete." He parrots his Grandfather's words to her.

"Shut up," she whispers brokenly, "Just shut up."

And then she flees, leaving him behind.


She emerges from their bedroom the next day, an effortless brittle smile on her face that reminds him of the Blair that appeared after Serena left for boarding school. She dodges Nate's attempts to talk, playing the loving ditzy wife.

She kisses his cheek when he leaves for work with his briefcase, "I won't wait up," she trills out as he flinches at the ice in her voice.

He grabs his briefcase and walks out.


She wonders for a long time whether she should leave her husband.

It would be easier, she supposes, to stay with him and pretend to be the loving supportive wife, then to out their marriage as a complete sham, despite the satisfaction it would give her to humiliate Nate and Serena, she knows that it would come at the cost of her own dignity.

And where would she go?

She knows that she can't raise a baby on her own, not Nate's baby. She can't. She needs someone, and an absentee Nate is better than no one.

So she stays by his side, and pretends, because that's all she's good for these days.


She buries herself in getting ready to be a mother.

When she had been younger, she had always assumed that she would be a typical Upper East Side mother, give birth through planned C-section or heavy epidural, hire a highly competent Nanny, and enjoy the perks of being a mother, without the work.

But the farther along with the pregnancy she gets, the more attached to her child she becomes. The child is the sole constant in her life. Without her baby, she has nothing, no one.

She shops for everything, by herself. She takes all the classes, by herself. She goes to all the appointments, by herself.

And every time the Doctor asks her, "No husband today, Mrs. Archibald?"

"Not today," she replies, "And please call me Ms. Waldorf."


She considers is a miracle when Chuck and Vanessa elope.

She doesn't have to sit through their wedding, watching the two of them promise to love and treasure each other.

Instead they throw a party to celebrate their marriage. She watches as the parade around the party, laughing and talking with their guests. Vanessa, an upcoming documentary filmmaker, fields questions about her newest documentary, and Chuck talks business. And they sound so put together and wonderful, Blair steams with jealousy the entire night.

She spots Nate and Serena dancing out of the corner of her eye.

Chuck and Vanessa. Nate and Serena.

And her.

Alone again. The constant theme of her life.

She rubs her slightly protruding stomach. "At least I have you," she murmurs softly, fighting off tears.


It was an accident, they tell her when she wakes up in the hospital.

She had been in a car with her husband, and it had spun out of control and smashed into a wall. She seizes her stomach in a panic. And it's flat.

"Where's my baby?" She screeches in panic.

The Doctor winces before he can control his emotions. "Mrs. Archibald, we were able to preform an emergency C-section, but your son's state is very precarious right now."

"Can I see him?" Tears are flowing down her cheek.

"Not yet. He's been transferred to the NICU, and they're trying to stabilize him," the Doctor assures her. "I'll have someone come and explain his case to you when we know more about your son."

The Doctor is halfway out the door when she thinks to ask about her husband.


Nate escapes the crash with a small cut above his eye, they don't even think it will scar.

She wants to scream. Her baby is fighting to survive and Nate is completely fine. She can barely look at him as he sits besides her, sobbing into her hands because it's all his fault. "It was Tripp," he explains in between sobs. "He was jealous of the attention Grandfather has been giving me, and he sabotaged the car. I'm so sorry."

"Nate," she says monotonously. "I don't care. Have you seen our son? How is he doing?"

"I—," he trails off; he looks towards Serena who stands in the doorway for support. "He's doing okay. The Doctors' say—."

"You haven't seen him, have you?" Blair guesses. "Too busy fucking your mistress to see your dying son?"

"Blair," Nate's voice is sharp, "Stop, that's not fair. And he's not dying."

"He's in the NICU because he was born too early because your psychotic cousin caused us to have a car crash. The doctors say that his chance of survival is 45%, the odds are not in his favor, and you don't have enough time to see your son?" She screams. "Get out. I want you gone, both of you."

They both look at her as if they want to say more.

"Go," she shouts, as they scurry out of her room.


No one visits her after that.

She expressly forbids the nurses from letting her husband in, or her ex-best friend. Her parents haven't made the flight from Paris (something about a storm keeping them from making the next flight out, she doesn't care anymore), and she doesn't have the energy to return their phone calls.

(There's only one person she wants to see, other than her son, and he's on his honeymoon, not due back for another few weeks.)

When she can finally leave her room, the first place she goes to is the Chapel.

She kneels before God and begs, "Please, you let me lose Chuck, don't make me lose my baby too. I can't live without him."

She prays and begs and barters until a nurse comes in and escorts her back to her room.


He is enters her room with pink peonies and a devastated look, and he's the first person to see her since Nate left.

"What are you doing here?" She sits up in alarm. "I thought you were on your honeymoon."

"I was," he admits, coming to sit beside her. "I was on the next flight out as soon as I heard."

"Must have been a pretty long flight," she says ruefully.

"Nate called Vanessa," he says with a hint of bitterness, "She didn't want to tell me, didn't want to ruin our honeymoon. My PI told me."

She's not even surprised he still has a PI following her.

"Do you know anything about my son?" She's desperate for news of him. His doctors keep her updated, but she knows that they hide things from her, worried about her fragile mental state. They only tell her about the small progresses or the miracles, not the struggles, which she know far outweigh the triumphs.

He looks downwards for a moment. "What do you want to know?"

"Everything," she breathes out.

So he tells her. He tells her about how dangerously underweight her son was, how the Doctors didn't think he was going to make it, how her son fought to live, how he was doing much better but would still have to stay in the hospital for a few weeks. He tells her that the Doctors don't think her son will suffer any lasting damage if he survives, but they are worried that he could develop some heart problems.

Her heart aches at the end, but she's grateful. "Thank you," she says sincerely.

He dismisses her with a wave. "Have you thought of a name?"

"Nate hasn't named him yet?" She asks curiously. She would have thought he'd have made that decision without her.

Chuck avoids her gaze again. "I don't think Nate's been around much."

"Think?" She raises an eyebrow; there are very few things that Chuck Bass doesn't know.

"Blair," he says softly, and she knows.

She closes her eyes. "He's sleeping with Serena," she informs him softly.

He takes her hand in his own. "I know."

Of course, she thinks. "I don't know why I wasn't good enough. Why aren't we good enough?" She thinks of her poor son struggling to survive, and the husband that just doesn't care.

"Of course you're good enough," he says fiercely. "Both of you are. You're better, in fact. More than Nate will ever deserve."

She opens her eyes, tears fill her vision. "Charles," she says suddenly.

"What?" He looks bemused, caught off guard by her sudden declaration.

"Charles Harold Waldorf," she says softly. "That's his name. I'll call him Charlie."

"Blair," Chuck trails off, not sure what to say.

"You'll be his Godfather, won't you?" She turns desperate eyes on him. She needs him, needs him to have this link to her son.

He says the only thing he can. "Of course, Blair. It would be an honor."


He stays with her after that.

She asks about Vanessa in the beginning. All her questions he blows off with a simple, "She understands" or "She's fine with it." Eventually Blair stops asking about Vanessa because she'd rather Chuck not remember his wife waiting for him at home. She becomes incredibly dependent on his presence at the hospital, even after her parents arrive. He's her rock, the one steady thing for her to cling onto.

She likes to pretend that he's there for her, for their son, instead of the fact that he's there because she's barely holding onto her sanity or because every day her son's health fluctuates like mad and the Doctors still can't give her a straight prognosis on whether or not her son was going to survive or because she has no idea where her real husband actually is.

He's there when they take Charlie off the ventilator, and there when her baby stops breathing at night (for a sudden horrifying moment), and there when she can hold Charlie for the first time, and there to wipe her tears when the Doctors tell her that Charlie is going to live, and there when the Nate finally shows his face with tears and flowers that she doesn't even like.

She's tempted to turn Nate away because Chuck is standing by her side, but Nate is Charlie's father so she lets him have a moment with her son and turns a deaf ear to any of Nate's questions about her own well-being.

"You need to back off," she overhears Chuck telling Nate later on. "She doesn't need your dick moves here."

"I'm her husband," Nate argues.

"You haven't been here for her," Chuck says furiously. "I have. And when you're gone again, I will still be there for her."

She can't help the large smile that overtakes her face.


She doesn't mean to overhear them.

She had gone looking for him a fit of happiness over the fact that the Doctors have finally gave her approval to take Charlie home, and she need to celebrate with him.

She barely rounded the corner when she heard his voice, harsher than she had heard him in a while. "Vanessa, what do you want me to do?"

"I want you to come home, Chuck," Vanessa is standing a few paces in front of Chuck, looking furious. "You just ran off on our honeymoon, and I find out from Nate that you're with Blair at the hospital. Then when I tried to come to you, you asked me to give you space, through a text, and I did so, because I know this is a tough time. But you've been here for weeks, Chuck. I haven't see you in weeks, because you've been spending all your time with Blair and her baby."

"Nate isn't here, I can't just leave her here alone." He argues back.

"But she isn't alone. She has her mom, Cyrus, Roman, and Harold," Vanessa lists. "She doesn't need you."

"She does," Chuck says firmly.


Chuck stays silent.

"I know that you two have a connection," Vanessa says suddenly, her voice a lot softer. "I knew that when we got in a relationship, and when you married me. I guess part of me always knew that you would always love her, more than anyone, more than me."

"Vanessa," he says softly, a bit pleading.

"Do you remember what I asked you when you proposed?" Vanessa said ruefully, crossing her arms over her chest protectively. "I asked you if you really wanted to do this, be with me. And you said yes. Well I'm asking you again, do you want to be with me?"

"I'm married to you," Chuck says, his voice growing a bit hard.

"And I'm asking if you still want to be?"

Before she can hear his answer, Blair flees. Her chest seizes up, because she realizes in that moment that even the slightest possibility of him saying yes, he still wanted to be with Vanessa, would devastate her. And in that moment, she knows what she has to do.


She considers leaving him a note, like he did that night after his father's funeral when he left her.

But she can't be that cruel to him, not after everything he's done for her.

So when all the plans are set and her father assures that he'd be delighted to have her and Charlie in Paris with them, she says her goodbyes to everyone and approaches him finally.

She's been steadily avoiding him for more than a week, requesting that he doesn't come to the hospital, and she knows that he's probably out of his mind with worry and furious at her for not talking to him.

She goes to his office before the airport.

"Blair, thank god." he stands up when he sees her. He looks so relieved to see her that she almost loses her resolve right there. "Do you know what you've been putting me through?"

"I'm sorry, Chuck," she says softly.

"No Blair," he excuses her immediately, "It's fine. I just don't know why you've been pushing me away."

"Chuck, I'm leaving."

He's silent for a moment, the relief washes off his face. "What?"

"I'm leaving New York," she looks away from him, because she can't look at him anymore, it hurts too much. "I'm moving to Paris with my dad and Charlie."

"Blair," he pleads with her, "I know things are tough, but you can't just leave. Nathaniel—."

"Nate and I are getting a divorce. It's going to be rough, but he knows we'll both be happier without the other. He's got visitation rights, but we agreed that Charlie will be better off with me." She dismisses, because Nate hasn't even been a consideration in everything.

"What about me?" He murmurs, and her heart breaks.

"Chuck," she says, voice cracking with emotion. "You have been amazing these past few weeks. I don't know how I could have made it without you."

"But you're still leaving," he finishes. "Even after everything?"

"I'm leaving because of everything," she explodes. "Don't you get it? I love you. I always did. I love you more and more every day, if it's even possible to love someone that much."

"You love me?" He stares at her dumbstruck. He straightens quickly, "Then why are you leaving?"

"Because you're married," she inhales deeply. "I can't be with you when you're married, and I can't let you leave Vanessa just because I said I love you."

"What if I love you too?" He looks at her intently.

She smiles brokenly. "It would make me insanely happy and devastated, but it wouldn't change my mind about leaving, so please, don't."

"Blair," he tries again. "New York is your home."

"And it always will be. But I'm a mother now, and I have to put Charlie first." She feels the tears well up in her eyes, but she refuses to shed them. "I will always love you Chuck Bass, but I can't play these games with you anymore. I need to put my son first."

"Of course," he looks as devastated as she feels, but he backs down. And she loves him even more for that.

"You'll visit, right?" She blinks and a tear falls. "I want Charlie to grow up knowing his wonderful Godfather."

"Of course," he repeats, looking down at his shoes.

She walks towards him and kisses him softly. "You're a good man, and a good husband, Chuck Bass." She pulls away, "Don't let this destroy all the good in you."

He nods, still not looking at her.

She walks away, and right before she slips out, she looks back at him. "Just because we can't be together, doesn't mean I won't always love you."

Even though she's leaving, he smiles softly. "I love you too."

She doesn't hear it.


Okay so a bit of justification. Like I said in the beginning, the first four chapters will not have Chuck and Blair getting together, so it's going to be a mess of angst and heartbreak and very very messy. However the last chapter will be so fluffy your teeth will rot.

Choosing people for Chuck to end up with was the hardest part because I felt like his love interests in the show weren't taken very seriously. Not like Blair's were. So I had to elaborate on them a bit. It might appear like Blair is more miserable in every chapter, but it's because this entire fic is through her perspective.

Believe it or not, this was sort of the hardest chapter to write because I started to bring Chuck and Blair together by the end. I hadn't planned to write the accident, it just happened. And as I was getting to the end, I knew that Blair and Chuck would end up together, which wasn't the point. So I ended it at this point. However, secretly, I believe that Chuck got on a plane and pulled of one of those grand romantic gestures that the Basses are known for. But you can believe what you will.

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