We know that Chuck did plenty over the course of six seasons (particularly seasons 1-4) to hurt Blair, but we rarely acknowledge the hell that Blair put Chuck through in season 5. It's really frustrating that the show never addressed how much she hurt him throughout that season - shutting him out after the baby, crashing his therapy session to change Louis, baiting him to be 'bad' and slapping him when he kissed her the way she wanted, accusing him of trying to win her back with the dowry, refusing to help him when he came to her as a friend, kissing Dan in his bedroom, telling him that she didn't love him anymore, etc. So many fics focus on Chuck's mistakes that I wanted to explore Blair as the one who needs forgiveness and needs to earn Chuck's trust back.
In this fic, pretty much all of season 5 is canon, except 5x24. Blair doesn't break up with Dan (yet), her diaries aren't leaked, and she and Chuck don't have any of the 5x24 conversations. Also, Bart does betray Chuck by cutting him out of the company, but he doesn't turn into a psychopath like season 6. This fic is set 5 years after the events of season 5, but I will include flashbacks to fill in blanks because there will be a lot of questions.
Prologue
"Mom? Cyrus?" Blair called out as she entered the Waldorf penthouse after a long day at the atelier. "Dorota?"
A familiar silence echoed back to her through the expansive foyer, and she sighed, setting her bag on the center table to sift through the mail. The stillness didn't bother her the way it used to, but the unyielding loneliness that she felt since returning home sank deep into her chest, causing her heart to clench from the weight of her past mistakes.
The stack that used to be brimming with invitations to galas and fashion shows now boasted little more than bills and letters from various solicitors. She tossed each one into the discard pile for Dorota to take care of whenever her next shift started, but she honestly couldn't remember when that would be. Since having her third child, Dorota had cut back her hours extensively, and since Eleanor and Cyrus spent most of their time in France, they hadn't bothered hiring additional help. Of course, Blair could take up the task herself, but it was just another item on her to-do list that she left unchecked.
As she reached the bottom of the pile, renewed excitement shot through her at the sight of an elegant envelope that had been opened and abandoned on the table. Her elation subsided a bit when she saw that the envelope was addressed to Mr. and Mrs. Cyrus Rose, but perhaps she would be able to accompany her parents to the event – anything to don a pretty dress and get out of the house. She let out a self-deprecating scoff at how pathetic she'd become. The name Blair Waldorf used to mean something, and now she was hoping to tag along with her parents to a social event to which she technically wasn't even invited.
She read slowly, her heart thudding in her chest with each word stamped on the paper. Her head grew dizzy as she tried to rationalize exactly what it was she held in her hand.
The pleasure of your company is requested
at the marriage of
Charles Bartholomew Bass
and
Caroline Amelia Whitlock
Saturday, the fifteenth of October
Two-Thousand Seventeen
at six o'clock in the evening
She dropped the stationery to the ground as if the embossed inscription would scorch her fingers. Her hands trembled, her eyes brimming with inexplicable tears, and she slumped against the wall. Her vision blurred and her knees buckled underneath her until she stumbled to the floor in a heap, one pitiful sob emanating from deep within her belly.
"Blair?" Eleanor's concerned voice called out through the fog clouding her mind some time later, but Blair couldn't be certain how long it had been.
She couldn't move; she couldn't acknowledge her mother. If she moved, if she stood, it would all be real.
"Blair?!" Eleanor's tone shifted to panic when she saw the invitation crumpled on the floor. "Oh, my God. Blair!"
She ran to fetch a glass of water and washcloth before dropping to her knees in front of her daughter. Frustration at her own recklessness pulsed through her body as she cried out to Cyrus to come help her carry Blair to her second floor bedroom. How could she have been so careless to leave the invitation on the table? It should've gone in the trash the minute it was opened, but she foolishly forgot about it when the atelier called with an emergency from another issue that Blair had neglected to rectify.
When Eleanor found out that Chuck Bass was dating one of Cyrus's most high-profile clients, she made her husband promise that Blair would never find out his involvement. He couldn't break his contract with Caroline without suffering serious professional repercussions. Honestly, he liked the girl, and she'd needed his help, but Blair's mental well-being always came first. For years, he'd managed to keep his working relationship with Caroline – and by extension, Chuck – a secret from his step-daughter. Now, though, this one small mis-step could prove to be enough to undo years of therapy.
XOXO
Chuck glanced halfheartedly over the 500-person guest list that his fiancé handed him. He'd attended enough big weddings to last a lifetime, but it was important to Caroline, so he swallowed his own selfish reasoning for wanting to keep a low profile and pretended to care about any of the people on the list – the majority of whom he didn't even know. When she'd asked him who he wanted to invite to the wedding, his own list was pretty short: Lily, Serena, Nate, and the Board of Bass Industries.
He flipped through the pages, barely registering most of the names until he came to the final page, and his chest clenched at the names staring back at him. He gripped the paper so tightly that it crumpled under the pressure. Caroline looked up at him from her iPad, narrowing her eyes at the destroyed list she'd spent hours creating.
"What is it?" she asked.
Chuck swallowed hard, clearing his throat before speaking. "The list is fine," he answered brusquely. "But I have to ask: why are the Waldorf-Roses on the list?"
"Cyrus helped me so much when I was trying to get out of my contract with Hartman Anderson. Why wouldn't I invite them?"
"It's just our wedding isn't a business affair -"
"Nonsense. More than half of your guests are from Bass Industries." She waved her hand in the air to indicate how utterly absurd she found his objection.
"Don't they spend most of their time in France anyway? Perhaps it would be best to save their invitation for someone who can actually attend."
"We're planning a six figure wedding, and you're concerned about two extra people?" Caroline flipped her auburn hair over her shoulder and let out a low chuckle. Slowly her face changed from amusement to understanding when Chuck exhaled through his nose. "Oh."
"It's not what you're thinking." He took a seat across from her, pulling her hands into his own so that he could soothe his fingers over her knuckles.
"This isn't about a girl you dated when you were nineteen? A girl you haven't even seen in five years?" Her blue eyes shone brightly, desperate for reassurance that her insecurities were unfounded.
"It's not about her," he spoke softly. "It's about the way we ended things. I just don't want to make things awkward for her. She's been through a lot."
"Well," Caroline gave him a sweet smile. "Good thing that she's not invited, so I don't see how it could be awkward for her. I've worked with Cyrus for years, and you've never said anything about it. It would be awkward not to invite him." She studied his expression carefully, still after two years together, struggling to read his emotions through his stoic countenance. "But, if it bothers you, we can remove them from the guest list."
He could see the vulnerability behind her eyes, and he couldn't bring himself to project any more of his demons onto her than he already had by simply being who he is. "No, it's fine; you're right. Cyrus should be there."
She grinned widely, wrapping her arms tightly around his neck. "I love you, Chuck."
He winced, returning her hug, trying futilely to ignore the guilt knotting itself together in the pit of his stomach. Every time she spoke those words to him, it felt like he deserved them less and less. He was a different man than he was years ago, thanks in large part to Bart's resurrection and subsequent betrayal, but he still struggled with emotions.
He knew that he loved Caroline, something that had both shocked and upset him when he finally came to terms with his feelings for her. It wasn't anything like he'd experienced with Blair; it wasn't volatile or passionate, but it was heartwarming and comforting. He sometimes wondered if it was the type of love that made more sense for a man like him. He didn't grow bored with Caroline the way he had with Eva; she was far more independent and self-assured than Eva ever was. She wasn't assertive like Raina, though, and she wasn't as competitive and stubborn as Blair. He hated comparing the few women he'd dated, especially the two he'd loved, but he couldn't help noting Caroline was in many ways an embodiment of his favorite qualities of the other three. She was intelligent, ambitious, loyal, and supportive. He trusted her more than he trusted anyone else in the world, and he was truly happy with her – a type of happiness that didn't come with stipulations. When he looked at her, he saw a woman who would always be his biggest champion, a woman who would always choose him.
"I love you, too," he whispered quietly, each word burning his throat. He ignored the sting spreading through his chest and pressed his lips gently to her temple, promising himself that no matter how screwed up he was, he would always protect her.
His biggest regret in life was that he hadn't been able to protect Blair - not when it really counted, and it led to the most painful years of his life. He'd be damned if he made the same mistake with Caroline.
Still, though, those words never got easier to say, no matter how true they were. He always felt like they belonged to someone else.
A/N: I know that original characters can be hard to accept. This is definitely a Chair fic, so, while Caroline will be a big part of the plot, she won't get in the way of the HEA in the end. I know it's also hard to accept that Chuck could actually love another woman, but we always see Blair 'loving' other men so I wanted to explore what it would be like if Chuck really did move on in the way he said he was trying to at the end of season 5. In reality, I don't think he would get into another relationship; I think he would just make work his life, but for this fic to work, we have to see him with someone else.
Also, I know that you were hoping for an update on Love and Loathing or Come Rescue Me, but this idea was dancing around in my head so I had to write it while I was thinking about it. Let me know if you're interested. :)