Chapter 2
Six Years Ago
Friends' Trip #1
Blair glared at her best friend in disbelief. "You're kidding!" she hissed, daring a peek through the rear window to the entrance of the building where Nate stood with his hands shoved into his pockets. "This is supposed to be a girls' trip for us to bond over hot guys. I've met my quota for charitable contributions this year, thank you very much, and I'd rather not spend my Christmas break watching you and Nate shove your tongues down each other's throats while fending off every lewd comment from that Basstard."
Serena sighed, "Come on, Blair. Chuck isn't that bad, but after everything that went down with the Captain this year, I really don't want to leave Nate here. Anne isn't exactly competing for Mother of the Year lately."
Blair's face softened slightly as she considered everything that Nate had been through. She shook her head, her nose snarling into a grimace. "Fine, but why does Chuck have to come?"
"Well, Nate refuses to leave him. His family is even more dysfunctional than mine or Nate's. If he doesn't come with us, he'll end up completely alone for Christmas."
Blair felt a twinge of an unfamiliar emotion knit itself together inside her chest when she glanced back toward the sidewalk to see Nate clasping his hand on Chuck's shoulder in greeting. She turned back to Serena and crossed her arms over her chest. "I don't see why I should suffer just because –"
"Ugh, Blair -"
"Whatever," Blair quipped just before the car door was yanked open, adding quickly, "Just keep him away from me as much as possible."
Serena smiled. "If I can't, then Eric or Jonathan will. You'll always have a buffer. Promise."
Less than eight hours later, Blair learned how little Serena's promises were actually worth when she found herself seated next to Chuck in a busy club. Jonathan and Eric had opted to stay in for the night, claiming jet lag from the long flight, and, as predicted, Nate and Serena snuck off somewhere after failing miserably to keep their hands to neutral territory on the dance floor.
Chuck lifted a scotch to his lips, expressionless, cold eyes fixed on the crowd of sweaty bodies writhing together to the beat of the music. He dropped the tumbler back to the table, the slight flare of his nostrils the only indication that something heavy was plaguing his mind.
Blair's eyes traveled along the clenched lines of his sharp jaw to the tension racking his stiff shoulders. She recalled Serena's words about his family situation. Rolling her eyes at her own softness, she moved to the bench beside him and popped the olive in her mouth from her empty martini glass. He arched a furrowed brow in her direction, and she shrugged with a smirk.
"It's Christmas, Bass," she waved the waitress over to their table, "And there's no room for another Scrooge this year."
He couldn't help the small upward pull at the corner of his mouth. When Nate had first introduced Chuck to Blair, they'd immediately butted heads. He found her entertaining, but she seemed to have little patience for his antics. When he wasn't in such a foul mood, he looked for ways to push her buttons, just to see what kind of rise he could get out of her. She usually tolerated his presence for their friends' sake, but this was new. "What do you have in mind?"
"Copious amounts of alcohol, of course."
"Hm," he sighed as the waitress replaced his glass with a full tumbler of premium scotch, "I like the way you think."
Blair raised her glass. "To forgetting this whole shitty year."
Chuck's eyes flashed, the bored scowl replaced by amusement. "Every year is shitty. What makes this one any different?"
"Whoa, that's such a bleak outlook to have on life at 20." She reclined back into the booth, naturally angling her body towards his with her martini glass dangling from her fingers.
"You learn through experience, I guess," he shrugged, pursing his lips together as he studied her more relaxed posture. "Back to my previous question. What made this year shitty for you?"
"I don't really want to get into the details," she answered, "But, long story short, my doting father filed for divorce from my mother after she discovered his affair with one of her models."
A humorless smirk spread across Chuck's lips. He couldn't count the amount of times he'd witnessed models half his father's age leaving Bart's office far more disheveled than when they had arrived. "Let me guess: she's no more than twenty-five with more surgeries than -"
"Bold assumption that she's a woman," Blair cut in bluntly. "Male model."
"I -" Chuck's mouth closed into a thin line, his brows knitting together to form a crease on his forehead. "Oh."
Blair burst out laughing. She'd spent too many hours crying over her father's betrayal, but, now with alcohol coursing through her bloodstream, the whole situation was absurd.
Chuck stared at her. "Are you okay?"
"I'm fine," she said between spurts of laughter, "But this whole conversation is a downer."
"What do you say we get out of here then?" He arched an eyebrow in challenge.
She nodded her head toward his scotch, and, lifting her own glass to her lips, she downed the rest of her martini. After he'd swallowed back his drink, she held out her hand for him to help her from the booth. "Lead the way, Bass."
An hour later, Blair's head was swimming in the most delicious way as she sat in a dive bar listening to off-key karaoke from the locals. If you asked her about this night in the future, she would deny ever having stepped foot in such a shithole, but, for tonight, it was exactly what she needed.
"You're up, Waldorf," Chuck gestured toward the make-shift stage.
"Um, no," she snorted. "I'd need a hell of a lot more alcohol in my system for that, but I'd love to hear you belt out some Celine Dion."
"Nice try." He narrowed his eyes playfully and motioned to the bartender to pour two shots of tequila. "But you're doing this. We're not on the Upper East Side anymore."
"You're not kidding," Blair laughed, snarling her nose as a burly man with a bulging belly let out a loud burp behind her. "Gross."
"Come on. No excuses." He pushed the shot toward her, reaching for her hand. Slowly, he raised it to his lips, just barely pressing his tongue to the back of her hand. Her eyes remained fixed on his, her breath hitching in her throat at the unexpected feeling of wetness against her skin. "Focus," he murmured, his eyes twinkling with mischief as he sprinkled a pinch of salt on the back of her hand.
When she didn't react, he lifted her hand to her own mouth. Something about the way he watched her felt entirely too intimate when she licked the same spot his tongue had just moistened. Finally, breaking eye contact for the first time in several beats, she threw back the tequila, immediately placing the lime in her mouth.
"Oh, God," she groaned, shuddering as the liquor rushed through her body.
"Now," Chuck grinned, "What song will you grace us with?"
Present Day
Friends' Trip #7
After a tense dinner, Blair was more than ready to call it a night. She felt a migraine working its way behind her eyes, and the mounting pressure made it even more difficult to put on a happy face in front of her friends. Sitting beside Chuck at dinner – listening to him regale their friends with fabricated stories of their past few months together in Paris, feeling his warm hand tracing circles on the exposed skin of her shoulder – caused her stomach turn in a mixture of rage and dejection.
Gathering on the sidewalk outside of the restaurant, the five others chatted excitedly about their plans for the rest of the week, but Blair remained quiet. Chuck's palm never left the small of her back; however, unlike the thousands of times before that she'd felt comforted when he'd let his hand graze her back while talking with friends, her skin now grew cold wherever his fingers lingered. It took everything in her not to shrug him off and distance herself from him. She couldn't fathom how he seemed to play into their lie so easily while she was barely holding it together.
She vaguely heard Nate ask, "So what're we getting into tonight? Maybe Enigma?"
"Nah," Eric shook his head. "I'm in the mood for something a little more mellow for our first night."
"Oh, there's that karaoke bar on 8th down by the park," Serena offered enthusiastically. Blair let out an involuntary scoff, causing Serena to roll her eyes. "Oh, come on, Blair. You can put your snobbery aside for one night –"
"Hm," Chuck cut in with a smirk, "Blair's well-acquainted with Tony's. In fact -"
She glared at him, horrified. "That's not…" she sighed. "I just have a headache. I think I'm going to head back to the house, but you all should go have fun."
"But -" Serena's face softened, her eyes reflecting the concern that she felt. She knew Blair well enough to know that there was more to the story than a headache.
"It's just jet lag," Blair waved her hand in the air dismissively.
"Hey, wait," Nate's face contorted in confusion, "What did you mean when you said that Blair's well-acquainted with Tony's? In all the times that we've been here, she's never gone -"
"Let's just say that when she's feeling -" Chuck started suggestively.
"Okay," Blair interrupted in a shrill voice, "My headache isn't getting any better with all this yapping. Have fun! I'll see you in the morning."
She quickly retreated from her friend's group, a cacophony of thoughts and emotions swirling in her mind. Within seconds, she felt a presence beside her and groaned outwardly when she looked up to find Chuck walking in-step with her. "What the hell are you doing, Chuck?"
"Walking with you."
"But why?"
"For the sheer pleasure of annoying you."
"If that's all," Blair narrowed her eyes, "then you don't have to try so hard. Your mere presence on this trip is enough to accomplish that."
"Yeah, well," he returned, sarcasm lacing his tone, "You've always made me want to aim a little higher, Blair."
If the metaphorical daggers that Blair shot from her eyes had the ability to wound, Chuck would lay bleeding on the sidewalk within a matter of seconds. Her frigid expression only served to elicit an exasperated huff from her ex.
"I'm accompanying you back to the house," he explained matter-of-factly. "It's what a doting boyfriend would do, right?"
"And which of those words is supposed to describe you?" she snapped.
"Both of them."
She scowled and kept walking, irritated that her stride wasn't long enough to outpace him.
"When in the past seven years would I ever have left you to walk home alone with a headache to go to a karaoke bar, Blair? I thought the point was to act as normal as possible."
Her eyes stung, but he was right. "Nothing about this is normal."
"I know." His words were quiet, and, for once, Blair didn't know how to respond. They walked side-by-side in silence for several minutes, an air of uncertainty growing between them.
"I don't want to do this," she whispered as if she was confessing a deep dark secret. "Tonight's been miserable – pretending I'm happy…pretending I'm still in love with you." She knew she wasn't being fair or truthful, but after he broke her heart, she'd never let him know that she'd die loving him while he'd eventually move on – if he hadn't already.
He was silent for several beats, and Blair felt the beginnings of regret and guilt knitting together in her stomach. Before she could apologize, he cleared his throat and said, "Maybe tonight was enough. Maybe tomorrow we'll tell them."
"Tell them?"
"We can tell them that things haven't been great for some time and seeing how happy they all are made us realize that we've grown apart."
Her chest ached; her eyes burned. It wasn't the exact phrasing, but it was close to what he'd told her months ago: "We were kids when we got together, and things are different now. It's time that we accept that."
"You -," she inhaled a shaky breath, "You don't think they'll suspect anything?"
"Blair," His eyes sparked beneath the streetlights. "They didn't even know we'd been hooking up for a whole year before we got together."
Her mouth fell open to respond, but what could she say to that? It felt like their secret rendezvous had happened in a different lifetime – one where they ended up together, growing old and dying happy in each other's arms. She had to guard her heart, so she refused to entertain those memories. Instead, she shook her head and said sadly, "We should've told everyone months ago."
"But we didn't." She could hear the same regret that she felt hidden in his voice.
At first, it wasn't intentional. She was too stunned and in denial, but a few days after their breakup, carefully wrapped packages showed up at Harold's chateau containing every single one of her belongings that she'd left at Chuck's place in New York. There was no note. It was so abrupt that she half-suspected that he headed straight to the post office after ending things.
After that, her heartache melted into anger. She mailed his stuff back the same day, tossing the 8-carat engagement ring into the bottom of the box recklessly – a symbolic representation of how carelessly he had treated their relationship.
Three days later, a courier hand delivered a neatly wrapped package to her, complete with the protective box that the ring came in. In a rage, she sent the ring back in a manilla envelope, hoping that it was damaged somehow in the mail.
When he got it, he texted her for the first time in two weeks: Keep the ring. It belongs to you.
I don't want it, she replied.
Days passed before he responded to her: Have you told Serena and Eric?
She paused, contemplating her answer. She hadn't told anyone, not even her own parents. Finally, she tapped out: Waiting until I can tell them at the same time.
After a minute, he wrote: Can we wait to tell everyone? Just for a little while? I just don't want to deal with it right now.
She found immense relief in that request, like perhaps they were just going through a rough patch and eventually everything would go back to normal. Maybe he really did just need some space.
Now, though, it seemed that putting off her problems to the future had made things infinitely more difficult. She sighed, stopping in her tracks and looking up into his eyes. She focused on the thin ring of yellow outlining his irises rather than the entirety of him. Being so close to him still knocked the breath directly from her lungs. "No," she said firmly, "We committed to doing this for our friends. We need to see it through until after the wedding."
His eyes closed for a moment. If she knew they would remain closed, she wouldn't be able to help herself: she would trace her finger along the line of his jaw to the curve of his mouth, not touching him but relishing in the near touch - the indefinable almost-but-not-quite that has always existed between them. She hated how utterly entwined they still felt, like her body would never stop trying to find its way back to him, like it didn't know how to exist independent of him.
His eyes slid open, and she averted her gaze, feeling as if she'd just been caught entertaining fantasies that were off-limits.
"They're going to ask questions," he said quietly.
"About?"
"When we last saw each other, how wedding planning is going, if we've set a date…all of the natural questions that would be asked of an engaged couple by their friends who haven't seen them in months."
"You're right." Blair resumed her trek back to the house as a means to sever threads still binding her to him. "We'll work it out tonight."
He nodded in acknowledgement, falling in step beside her once more.
"How's work?" she asked after a few moments of silence stretched between them. She hated that it sounded like small talk.
Chuck opened the door for her as they reached the front entrance. "Good."
She waited for him to elaborate, and, when he didn't, her heart clenched tightly. It stung the way he'd meant for it to, a reminder that she wasn't entitled to more information about his personal life than that single-word reply – a noncommittal response one would offer a complete stranger.
He softened when he saw her face drop. "Bass Industries is doing great. I took control from Jack two months ago, so it's been a transition, but, truly, it's going well."
As they made their way up to the bedroom, the awkwardness of the situation seemed to dissipate for the time being. Chuck asked about Harold and Roman, and Blair told him horror stories of working under the dictatorship of Eleanor Waldorf. He laughed, the first true genuine laugh she'd heard from him in half a year, and a bittersweet ache spread through her chest. God, how she missed him – and how she hated herself for it.
"By the way," she arched an eyebrow in his direction as she lowered herself into a large lounge chair, "Consider this your warning: if you ever tell them about my one and only foray into karaoke, I will actually castrate you."
A sly smirk spread across his lips. "Don't worry. That's a memory I want to keep all to myself."
With a wink, he left her to her night-time routine. A little while later, after scrubbing the day's stress from her face, she settled between the sheets of the enormous bed. Sleep couldn't come soon enough. As she flipped off the lamp on the bedside table, the door to the bedroom creaked open, allowing a soft glow to engulf the room.
"Hey," Chuck whispered softly. "I didn't mean to wake you."
"I wasn't asleep yet," she said, wrapping the sheets over her chest in an attempt at modesty that she'd never previously needed around Chuck.
Carefully, he made his way to her side of the bed and handed her a small teacup and saucer.
"What's this?"
"Herbal tea," he explained. "You said you have a headache."
What was meant to be a gesture of kindness - something to bring her relief – cut so deep that she was certain the wound would never heal. "Thank you," she spoke quietly, her voice breaking at the end.
"Anything for you, Waldorf," he rasped, as he gathered blankets and pillows to form a make-shift bed on the floor.
"Chuck -" she started, setting the teacup on the nightstand. Her heart beat an unsteady rhythm, panic sinking into the pit of her stomach.
"You should get some sleep. Goodnight, Blair." His words held such finality that she didn't dare respond. There really wasn't anything left to say anyway.
Six Years Ago
Friends' Trip #1
"Oh, my God!" Blair squealed, running off the stage after she finished her performance. Quickly, she grabbed Chuck's hand and yanked him toward the door. "I cannot believe I just did that."
Once they hit the sidewalk, he pulled her into a hug, relishing the feeling of her body against his. "You were amazing."
She wasn't sure if it was the liquor, the city, or the warmth of his skin against hers, but she couldn't think of a single reason to heed to her inhibitions. In a moment of boldness, she placed her hands against his shoulders and pushed him backward until he was engulfed in the darkness of an alley.
His back hit the stone wall behind him, and he husked "What are -"
Before he could finish the question, her mouth was on his, her tongue pressing insistently against his lips. For a beat, he remained still, shocked. As if every sensation in his body awoke at the same moment, his hands wound around her waist, flipping them so that he could press himself into her. He returned her kiss with fervor, running his hands over every exposed ounce of skin he could find.
He tore his mouth from hers, trailing his lips down her jawline to the column of her throat. She wrapped her arms around his neck and thread her fingers through his hair, anchoring herself to him. His palms slipped up her torso to cup her breasts through her dress, causing her to arch into his touch.
"God, Blair," he groaned, kissing a path to her ear, his breath hot on her neck. "You taste so good."
Hearing her name from his gravelly voice sent shockwaves through her, and reality hit her like a brick. She pushed him away, shoving at his shoulders until he disentangled their bodies. "We can't do this," she panted between heavy breaths.
"Why not?" he whined petulantly.
"You know why," she said. "It'll get too complicated. If things go south…"
"Good thing neither one of us is emotionally invested then."
She ignored his protests. "We're friends now, right?"
"Yes, we are," he agreed. "You've heard of friends-with-benefits, haven't you?"
"It's not that simple. We share four best friends." Blair adjusted her dress, putting more distance between them. "We can't risk that for sex."
"It wouldn't just be sex," he smarmed. "It'd be the best sex of your life."
"Chuck -" she sighed, trying through the haze of alcohol to ignore that very excellent point.
"Okay," he grinned. "You're right, but that doesn't mean that I'm not going to imagine what could've been."
"Have fun with that, Bass," she laughed.
"Oh, I fully intend to as soon as we get back to the house."
She shook her head, unable to resist the smile that pulled at her mouth. He offered her his arm, and she looped hers through the crook of his elbow. It was a small concession – at least she was touching him, even if it wasn't the way either one of them desperately wanted.
For the remainder of the week, Chuck kept his behavior in check. While he would never suppress the occasional innuendo, he respected Blair's boundaries. They spent each night of the trip talking about every topic possible – childhood dreams, embarrassing moments, biggest fears, role models, political candidates. Slowly, by the end of the week, Blair's view of Chuck completely shifted. She no longer dreaded his presence; she missed him in his absence and counted down the days until she could see him again. For a year, they never mentioned their first kiss, maintaining clear lines of platonic friendship.
Of course, the second friends' trip was a different story entirely. If you draw a line in the sand, it's only a matter of time before it gets erased.