A/N: Because if the writers aren't going to fix it, then someone has to do it for them. There aren't any spoilers for the show in this. The waitlisted thing is in the books, so I stuck it in here because it worked.

***

He stares at the flowers on the floor the entire elevator ride down, trying to accurately label the emotion that he's feeling. His intestines feel like they're being squeezed by an icy hand, but his face feels the opposite, his cheeks burning several degrees too hot. He thinks about the disappointment he saw etched on her lovely face as the doors closed on her and the fact that it was him who put it there. He remembers his actions of the past 24 hours and his face flushes hotter.

It's only when the elevator dings and the doors open to reveal the lobby that he finally realizes what it is: shame.

Before he exits, he picks up the sad-looking peonies from the floor. He doesn't stop to think about why.

***

The bouquet lands on his nightstand next to a generous glass of scotch that he's poured for himself. He stares at his reflection in the mirror as he rips off his father's tie and thinks that he might hate her.

On days like these he wishes that things could go back to the way they were before; before she danced onstage in front of him and captured his heart with one fatal swivel of her hips. Because he was perfectly content with his life before her. Back then things were simple, when all he did was laugh, smoke, drink, and fuck without sparing a second thought on just how empty he truly felt. Sometimes he wishes he were still empty.

He thinks that maybe she's the worst thing that's ever happened to him because he's never felt more wretched than when she's turning her face away from him in disgust; and he's never felt lower than when she's hurting because of him. But then he remembers what it felt like when her teeth tugged on his bottom lip while he kissed her, and what he saw when she looked into his eyes right before she was about to come, and he knows that she's quite the opposite of the worst thing.

He knows he doesn't deserve her, but he wishes he did. (On days like these, he wishes for impossible things.) He drains his glass and wonders what it would be like to be a better man.

***

He can't bear to look at his uncle, and contemplates moving out of his suite just so he can be away from him. Every time Jack looks at him with that smug smirk, he wants to punch him in the face, because even though he'd like to blame losing Blair on his uncle's machinations, Chuck knows that Blair's right: he has no one to blame but himself. Jack may have set the trap, but he's the idiot who so willingly walked into it. And that thought only serves to make him want to punch his uncle even more. (It's all a vicious cycle, really.)

And while he knows that it wasn't Jack's fault, the fact remains that his uncle is still an asshole who set up his own nephew in order to gain control of the company, and that makes their relationship unsalvageable. So when Lily invites him to dinner, he accepts because he realizes that he can't really afford to be angry at her anymore. Considering that all the other parental units in his life are either assholes or, well, dead, he figures that Lily was the only adult who ever had his best interests at heart. There's also a plan formulating in his head, and Lily's support is key.

The dinner is not as uncomfortable as he thought it would be. He keeps it strictly business when he asks Lily to be his guardian, explaining to her that she'd control the majority shares of Bass Industries. The plan doesn't seem to faze her, however, even when he tells her that he might have to move back into her penthouse. In fact, she smiles warmly at him and tells him that she'd like it very much. He's slightly confused, but it's her next words that render him mute: she tells him that she's pregnant with his little brother or sister.

Suddenly he feels so completely unprepared.

***

He's sitting at a table in the courtyard at school waiting for Nathaniel (who is late, as always), when Blair takes a seat next to him. She's been avoiding him for over a week, and he's momentarily confused into silence.

"Congratulations on the new sibling," she says.

"Uh. Thanks."

"How does it feel?"

"I really haven't had the chance to process it, to tell you the truth," he replies. She gives him a small smile and, for some reason, he just can't leave it alone. "I thought you were done," he says, with no hint of accusation or smugness in his voice, just genuine curiosity. It's probably because of this that she decides to answer.

"Done with the fantasies and expectations," she says with a small shrug. "Not done completely. If you think about it, we've been friends for a really long time, and it would be a shame if we couldn't put all the crap aside and just be there for each other…as friends," she finishes lamely.

Relief floods through him, but the smile he gives her is small. "It definitely would be a shame."

Her smile to him is just as small, but he feels happier than he has in weeks.

***

The papers are signed and he moves back in with the van der Woodsens at the end of January. Serena huffs a breath and rolls her eyes at him, though the corners of her mouth quirk up in a smile. Eric just launches himself at Chuck in a tight hug and tells him that he's glad to have his brother back. Chuck privately agrees.

Lily tells Jack that his presence in New York is no longer required. Chuck buys his uncle a Cartier watch as a going away gift because even though he's trying to act more like an adult, it's going to be a long time before he decides to forgive and forget.

***

His acceptance letter to NYU shows up on the 2nd of February. The envelope is thick, so he knows he got in before he even opens it.

Dear Mr. Charles Bass,

New York University is pleased to offer you undergraduate admission to the Leonard N. Stein School of Business…

He allows himself a small smile, but doesn't read the rest of the letter. He frankly doesn't even remember applying to NYU, and wonders how many millions his father had to donate in order to get him there.

***

It's like déjà vu when she sits next to him the next day as he's waiting for Nate in the courtyard.

"I feel like I keep saying this, but, congratulations," she says. "Again."

"On what?"

"On getting into NYU."

He hasn't told anyone yet, but he's not really surprised. "Wow, good news travels fast, considering I haven't said anything to anyone about it."

"Serena saw the package," she explains.

"Of course," he says, because, of course.

"Not that a degree is necessary," she continues, "considering you'll be CEO of Bass Industries when you turn 18 in 3 months."

"I've already filled out the acceptance form. Just have to mail it in."

"Oh." She's clearly surprised. "I just never thought you were serious about school, or college, or anything."

He gives her a meaningful look. "I'm serious about plenty of things, Waldorf. Besides, it's one of the top business schools in the country, and I think a degree in business might come in handy if I'm going to take over a multi-billion dollar company. I know I was born gifted, but I wouldn't mind learning a thing or two."

She says nothing, just stares at him unabashedly.

"What?" he asks when he can no longer take her searching gaze.

"What's going on with you, Bass?" she wonders quietly.

He shrugs. "Nothing. Just trying to better myself, I guess. Why is that so hard to believe?"

Her eyes scrutinize him again for a few seconds, but she leaves without answering his question.

***

Yale sends out its letters a couple days later. Everyone in the van der Woodsen-Bass penthouse is thrilled when Serena is accepted. It all goes sour, however, when they find out that Blair has been waitlisted.

He wants to speak to her the next day, but she's not at school and won't answer any of his calls or texts. He's pretty sure she's plotting her way to the top of the waiting list, or planning the downfall of some naïve future freshman (she's Blair fucking Waldorf, after all), so he decides to leave her alone for the time being and waits for the hammer to fall.

Only it doesn't. He gets a text message later that night from Serena as he's dozing trying to finish his calculus homework: R u home? B's wasted. Downstairs. Help! -S

When he finds them at the Palace bar, Blair is drunker than he's ever seen her, including those couple days after her father left, when a martini glass seemed to be permanently attached to her hand (and even then, she only ever got tipsy-bordering-on-drunk, because even at her lowest, Blair never wants to lose what little control she can grasp). Serena is on the verge of tears, making her practically useless, so Chuck takes Blair's arm and wraps it around his neck while he puts his own arm around her tiny waist and practically carries her to the elevator. She's light as a feather. They climb into the elevator and Serena pushes the button and explains that Eleanor is at home and Blair doesn't want her mother to see her this way.

"How much did she drink?" he asks.

"I stopped counting after her 5th martini."

Up in the penthouse, he deposits her on Serena's bed while Serena goes to get her some water. He sits beside Blair on the bed and looks down at her. Her eyes are closed and several strands of hair have fallen over her beautiful face. He gives in to the impulse and takes his hand to brush the stray locks behind her ear, ignoring the way his chest tightens at the gesture. "Do you need to puke?" he asks her.

"Do you need to puke?" she counters, her eyes still closed. She's silent for a moment before a frown line appears between her brows. "Why is it never enough?" she asks pathetically, her voice small and quivery. "I give and I try and it's never enough…" She trails off muttering about stupid Yale, and stupid Daddy, and, finally, stupid Chuck.

Something inside him clenches painfully when she says his name. He tries to talk past the knot forming in his throat. "Maybe they don't think they deserve you," he says gently.

Her bottom lip quivers and he's about to panic thinking that she's going to cry, but what she does is something he never expected: she blows a giant raspberry at him, spraying half his face. "Pffffffft."

He laughs quietly and amends his answer. "Or maybe we're just fucking idiots who don't know a good thing when we see it."

"That must be it," she concurs with a sharp nod.

Chuck privately agrees, because looking at her now, he knows that he was indeed a fucking idiot for not valuing what he had when he had it. He thinks that if he had it again, he'd appreciate it that much more.

Serena finally shows up with a bottle of water and he asks her if she had to pull it up from a well because she took so damn long. She rolls her eyes at him, and he takes it as his cue to leave, but he can't help himself so he presses a kiss to Blair's temple. And because he knows she won't remember this in the morning, he whispers secrets in her ear. "I'll figure it out one day, Waldorf. Then I'm going to marry you."

He walks toward the door, but before he can leave, Blair yells out to him from her place on the bed. "Like I'd say yes," she scoffs.

He chuckles as he closed the door behind him because he'd like to think that she would.

***

She doesn't mention Yale again to him, choosing to tell him instead that she's having such a hard time deciding between Harvard, Princeton, and Columbia; all preeminent institutions of higher learning with impeccable standings and storied histories, and who would want to live in Connecticut anyway?

He doesn't believe her because she doesn't even believe it herself, but he doesn't say anything to her about it and just watches her as she keeps herself busy planning her Valentine's Day party. A part of him wants her to pick Columbia because then they would both be in New York in the fall, but he knows she's always had her heart set on Yale. And if that's what she wants, then he was going to try his best to help her get it, because somewhere along the way her happiness became more important than his own. He considers it an unfortunate side effect in his quest to become a better person.

***

The day before Valentine's, Blair bursts through the doors of the penthouse elevator while they're all having dinner, throws herself on Serena, and incoherently babbles about Yale through sobs. He's on the verge of putting out a hit on someone when he realizes that it's that weird sort of happy crying that girls sometimes do.

It takes almost five minutes for her to calm down enough to tell them why she's there: Dean Berube had just called her not half an hour earlier to congratulate her on her admission.

Everyone is elated, no one more so than he, especially when she throws her arms around his neck and hugs him. He's kind of shocked because they haven't had this much physical contact in weeks, but he squeezes her tightly anyway (ignoring Lily and Serena's secret smiles over Blair's shoulder), glad that she's letting him bask in her happiness. Champagne is uncorked to celebrate and Blair is giddy and radiant, like the weight of the world has been lifted off her shoulders. She and Serena screech about what residential college they'll be placed in, who they can bribe in order to room together, and when they can come home for weekend shopping trips. He makes a mental note to google the distance between Yale and NYU.

He sends her an enormous bouquet of flowers the next day, justifying it to himself by claiming that it was just his way of saying congratulations. It was just a coincidence that it happened to be Valentine's Day.

***

Lily approaches him a few days later with a very serious look on her face and a request to have a meeting about his finances. He tries not to be too annoyed because she is his guardian, after all, and he's not one to be mean to pregnant women. While their relationship was still a little formal, it wasn't strained, and he wanted to keep it that way.

"Charles, I'd like to know why the bank called me yesterday o inform me about a 10 million dollar transaction posted to your account."

He decides to play it cool. "There was a very important…opportunity that presented itself to me. I couldn't pass it up. I apologize that I couldn't let you know beforehand."

Lily looks at him with searching eyes, studying him, and he begins to feel a little uncomfortable under her gaze. Suddenly she smiles, surprising him. "I just wanted you to know that you can come to me with these things. You don't have to do things behind my back because I will always try to listen, and maybe even be able to help. And I know you're turning 18 in less than three months, and you won't legally need a guardian, but my door will always be open to you."

"Thanks," he replies, a little confused as to what brought this on. "I'll keep that in mind." He gets up to leave, but her voice stops him.

"Oh, Charles, one more thing," she begins, the corner of her mouth moving upward in apparent amusement. "Dean Berube called me this morning to thank me for Bass Industries' generous 10 million dollar contribution to his university. I guess I should pass that thank you along to you."

He attempts to shrug it off. "Well, I've always been a patron of higher education." He gives her a serious look, but she says nothing, only quirks the other side of her mouth upward and she's smiling at him fully now, grinning like the cat that ate the canary, and he just sighs in exasperation because, well, he's busted. "Please don't tell Blair."

"I won't," she promises and makes that ridiculous hand gesture like she's locking her mouth with an imaginary key, but her smile is wider than ever, and all he can do as he leaves is roll his eyes.

***

He knows the jig is up on Wednesday when he sees her marching purposefully towards him in the hallway at school, her Jimmy Choo Mary Jane pumps clomping out an angry beat on the floor. He schools his features to display disinterest, but the temperature rises under his collar.

"Is it your mission in life to humiliate me?" she asks in an angry whisper, looking around to see if anyone is paying attention to them.

"What the hell are you talking about?" he asks with feigned nonchalance, digging around in his locker just to give his hands something to do.

"You know damn well what I'm talking about, so drop the 'Who, me?' act. I can't believe you would do this to me."

He sees the angry tears in her eyes and deflates. "I told Lily not to tell you."

"She didn't. There are other people who live in that penthouse."

"Dammit, Serena," he sighs, irritation at his step-sister flaring.

"Every time I feel like we're making some sort of progress, you turn around and do something that ruins everything. How could you do this?"

He sticks his hands deep in his pockets and shrugs, feeling helpless as he looks into her eyes. "I was just trying to grease the wheels a bit. I know how much going to Yale means to you."

"I don't want to be indebted to you," she spits

"Indebted?" he asks incredulously. "I didn't do it to have you in my debt. If anything, I'll always be in yours for everything you did for me when…" He glances away, unable to look at her. He doesn't like remembering how far down he spiraled. "When my father died," he finishes softly. "I was only trying to help, Blair. I swear."

She narrows her eyes at him, but he thinks she might believe him. "Why? What's in it for you?"

Her suspicion only increases his frustration. "Is it so hard to believe that a guy could do something nice for a girl without expecting anything in return?"

She's momentarily speechless before she lets out a weird breath, like a laugh/scoff hybrid. "It's not hard to believe any other guy could do that. But you're Chuck Bass."

"And you're Blair Waldorf. And though you may not believe it, I want you to be happy. Because I care about your happiness above all others, including my own."

"Since when?"

And this is the moment he decides to tell her the truth, because he's so damn tired of going in circles. "Since the day I realized that I love you more than even myself."

She's stunned into silence, and her mouth opens and closes several times without any words coming out. He almost wants to laugh because the sight of her gaping like a fish is actually kind of funny. Instead he closes his locker and walks away.

***

After school, he's sitting on the steps outside waiting for Serena and Eric when she sits beside him, looking anywhere but at him. "I don't know what to say," she begins gently.

"Then don't say anything," he offers.

She doesn't for a while and he wonders if that's the end of the conversation. Finally she says, "I'm still annoyed with you."

He smirks, because he already knew that. "And I'm still sorry about that."

His hand is resting on his knee and she puts hers on top of it, pushing her fingers through his, interlocking them. He stares at their joined hands and his stomach starts with that stupid fluttering. She leans into his shoulder. "We only have two months til graduation. Maybe it's too late."

He lifts their hands to his mouth and kisses the back of hers. "We still have the summer."

"And then I'm off to New Haven in the fall," she points out softly. "I don't know, Chuck. Do you think we can do it?"

"I don't know, but I don't mind trying. Besides, Yale and NYU are only 78.9 miles apart."

She pulls away from him so she can look at his face, a smile already forming on her lips.

"What?" he asks, trying not to feel embarrassed. "I googled it."

Her smile just widens, and even though he's trying not to because she's making him feel stupid, he can't help but smile back. She's never looked more beautiful. "You googled it?" she asks, her voice rising several octaves on the second word.

"It's no big deal," he insists. "You type in one address, then another, then you click--"

He doesn't finish his tutorial because suddenly her lips are on his and talking is the furthest thing from his mind.