A/N: This is my third fanfiction, one that I've been planning for months, which may or may not end up as a series depending on the response I receive. I usually write one-shots, but I have a few ideas as to where I want to go with this. One possibility is continuing the plotlines of Season 1, only with the Roaring Twenties as the setting. Another is diving into the Great Depression with Blair losing her home and having to move in with the Van der Basses? Please read, review, and tell me what you think!

Blair's mother would surely die if she saw her now. Two identical rosy circles of rouge adorned her cheeks, her face framed by a sleek dark bob, which was all the fashion nowadays. Though her dress was certainly more modest than Serena's, whose hemline was pushing even the most lenient boundary of society's dress code, it did show a fair amount of leg, tantalizingly obscured by stockings rolled down to her knees (well, a girl had to dance). To top it off, she had snuck her grandmother's prized pearls out of the house; they were now fashioned into an elegant ring around her head. Though Blair knew she had taken a huge risk by doing so, she always had to have the best in accessories. After all, she was Queen B of the Upper East Side and the Roaring Twenties was all about taking risks.

"My God, Blair! Those pearls are the cat's pajamas!" one of her minions crowed. "Who's the designer?"

"My mother, of course. All of the ladies in Paris are wearing them." The cluster of girls around her tittered and she smiled to herself, knowing that by tomorrow, at least half of the junior girls would also be sporting pearls around their heads. It wasn't long before Nate arrived and Blair had scooted to his side, the very image of the model girlfriend.

"Hey, honey. I missed you," she murmured. "Where've you been all day?" She could already smell the liquor on his breath. Her smile dissolved as she spotted his best friend lurking behind him. "And you brought Chuck. Charming."

"Oh, sorry. Chuck has this plan to buy a speakeasy and I was helping him with the proposal for his dad." Blair cocked an eyebrow at Chuck, who quickly put on his most innocent expression.

"Natie!" squealed Serena, launching herself into a bear hug that lasted just a little too long. Blair frowned.

"Waldorf," Chuck said in that flirtatious manner of his, taking the opportunity to step closer as Serena chatted with Nate. "Well, aren't you the doll tonight?"

"What ever happened to your gang of quiffs? No one to entertain you tonight?"

"None as keen as you, I'm afraid." He tried to wrap an arm around Blair's waist, but she swatted him away.

"Careful, Bass. Wouldn't want Nate to find his pal putting the moves on his girl. Especially after all the help he gave you with the speakeasy."

"And here I thought Nate was the gullible one."

"What do you mean?" Blair demanded, crossing her arms. Chuck raised an eyebrow suggestively.

"Oh my God!" she said. "What were you two really doing at that speakeasy?"

"I believe the better question would be, who were we doing at Victrola." Chuck laughed at Blair's scandalized glare.

"Relax. Your perfect boyfriend kept his hands to himself. The two of us got a little bent. Me on the other hand? Well, if you saw the gams on that Rosie, you'd—"

"You're disgusting," Blair cut in.

"You're just jealous."

"What?!?"

"Admit it, you're not as much of a bluenose as you want us to think." Chuck leaned in closer, backing Blair up until she was cornered against the wall. I know you're just dying for a taste of what I have to offer." With his warm breath on her face and his eyes drinking her in, Blair suddenly regretted sewing up the hem of her dress. Under his leering gaze, she felt as if she was wearing nothing at all.

"You are presumptuous. I don't know why I'm even friends with you."

"Oh, you know, I'm sure." Chuck grinned at her. Her eyes changed and she lifted her fingers up to his face to tenderly graze his cheek. His face suddenly lost all its laughter as she placed her warm hand on the back of his head, wrapping her slender fingers in his dark hair. In spite of himself, Chuck began to close his eyes in anticipation of the kiss. That's when she grabbed hold of his ear and tugged, hard.

"Owww, what the—" his eyes flew open to glare at her, but she was already gone.

Later, at the same party.

The night was only getting started. Serena had leapt up onto the bar counter and was dancing to the upbeat, brassy sounds of the jazz band assembled in the corner. She kicked out her feet and waved her arms to the music, the silver fringe that hung from her tiny dress spinning out. Even when she was completely zozzled, she still managed to look graceful as she danced, her pale yellow hair seeming to emit its own glow.

Blair was trying and failing to keep Nate's attention. The poor girl really stood no chance when Serena was up on the bar in all her blond glory. Every girl seemed to be facing the same struggle as all the males in the room stared at her, transfixed.

"I'm going to get her off the bar!" yelled Blair over the music.

"What?" replied Nate, completely oblivious, as Blair detached herself from her boyfriend.

"Oh, forget it." Blair made her way through the throngs of drunk people, who stank of sweat and booze. She climbed up onto the bar, and all of the men hooted. It had been the longtime fantasy of many to see the two hottest girls in the city dancing in their short little dresses—and perhaps, doing a bit more.

"Keep dreaming!" yelled Blair to the catcalls and wolf-whistles. "Serena, come on. We're leaving." Serena, however, had no intention of leaving.

"But Blairrr," she slurred. "We're only just starting. And this is funnnn," She howled to the crowd. "Am are 'ight!" The din became deafening as the crowd howled back. "Dance with me!" She threw her hands up in the air and twirled around, stumbling slightly. It was no easy feat, dragging her down from the bar, as she was at least four inches taller than Blair, not to mention fighting back the angry protests from the crowd.

"Really, it's nearly two in the morning!" she yelled to one. "Oh, screw, you rummies!"

Serena, Blair, Nate, and Chuck had finally made it outside and were halfway to Chuck's brand new, state-of-the-art stretch limousine when the disastrous happened. Serena stumbled, grabbed for Blair's neck, and missed. Before Blair could blink, the chain of pearls had been ripped off her head, the string snapped, and pearls spilled out across the pavement.

"Oh, FUCK!" Blair cried out, immediately down on her knees, scrambling to capture the pearls as they rolled away. "Goddamnit, Serena!" Both Nate and Chuck watched in stunned silence as Serena began retching behind the car and Blair quickly dissolved into a mess, sprawled on the pavement in tears.

"That was my grandmother's pearl necklace," she sniffled. Nate looked at the ground, unsure of what to do. Chuck got down and put an arm around her. He was taken aback when she flung her arms around his neck and sobbed on his shoulder. Not knowing what else to do, he pet her hair rather awkwardly, motioning to Nate to take his place. Nate, however, shook his head insistently and looked at Serena.

"My mother is going to murder me. Oh, God, I'm as good as dead." Chuck motioned to Nate to clean up Serena, whose puking sounds were starting to subside.

"Tell you what, Waldorf. Let's bring you home first and I'll see what I can do. "Nate, can you bring Serena home in a cab?" Nate nodded and immediately flagged one down.

Chuck guided a distraught Blair to his limo and directed the chauffeur to drive to Blair's apartment. "Now what kind of pearls were they?" he asked as the vehicle began moving. Blair stuck out a shaking hand, tightly fisted around the pearls she had managed to rescue from the sidewalk. Chuck slowly pried open her fingers and pocketed a few, all the while shushing her gently.

"Now when you get home, you're not going to tell your mom about the pearls. If she misses them, tell her you lent them to Serena. Promise me you'll do this and I'll take care of everything." Blair nodded between sobs.

"I'll see you in the morning."

It had been a rough night. Half-lucid dreams of her mother discovering the empty velvet box and demanding the pearls were gnawing at her resolve to simply concoct a story to tell Eleanor of the missing necklace. Blair had cried herself silly, her pillow drenched, and her eyes unfortunately rimmed in red.

At around six in the morning, a very weary, but beaming Chuck knocked on her door and, without invitation to enter, stepped in. She looked up briefly to see who it was, then immediately buried her face in her pillow. To have Chuck see her in such a state—it was nothing short of unbearable. Chuck, however, thought that she looked, if possible, even more beautiful in her vulnerable state.

"Why the grin?" she sniffled. "Can't you see I'm about to face my execution?" He smiled wider at the knowledge that even devastated, she could put up such a steely front against him. Gently smoothing the sheets, he took a seat on her bed.

"You're such a bearcat, Blair. But that's why I like you."

"Oh, spare me. Why can't you go harass some other Jane."

"Alrighty then. I'm leaving. But maybe she would appreciate this nifty present." At the word "present", Blair's head popped up, overtaken by curiosity. He chuckled.

"Knew it would get your attention." He pulled a sleek, beautifully wrapped box from behind his back and handed it to her. She delicately untied the silver ribbon and opened it, fully aware that he was watching her face with anticipation.

It was a pearl necklace. Blair let out a cry of delight, nearly crying again in the process.

"Exactly like your grandmother's. I showed the jeweler the pearls. Rare ones, too, they were, but he tracked them down."

"But no jewelry store is open at one in the morning."

"They'll open for a Bass." She realized how much he had went through to get them to her before Eleanor returned from her trip.

"Do you like it?"

"Oh, Chuck! It's the berries!" She carefully placed it back in its packaging and stuck out her hand stiffly. He took it, then pulled her close to wrap her in a hug.

"Don't push your luck," she chided, though she really was too glad to care.

"Oh, you know I will." She pushed him off.

"Now, how about we go replace the necklace before your mom gets back." She threw back the covers and leapt up, all thoughts of the night before forgotten and wrapped a sheer white robe around her lavender nightgown. Giggling, the two of them hurried off to her mother's enormous bedroom, which lay dusty and mostly unused. While Chuck locked the door so that they wouldn't be caught by Dorota, Blair stood on her tiptoes and extracted the velvet box from its high shelf. After he had placed it in, they replaced the box and tiptoed to the closed door, just in time to meet—

"Mom!" Blair gasped, as they swung open the door to her bedroom. "You're early!"

"Blair Cornelia Waldorf!" came the stern reply. "What on Earth are you doing in my room! With the door closed…with a boy!"

"Well, Mom, I really—"

"Blair was just giving me a tour around the apartment when I expressed curiosity in viewing the rare van Gogh she mentioned you had acquired recently," Chuck drawled, almost lazily. "I'm doing a project on him for Art History, so why not view a real work of his, I thought." Chuck gave her his most innocent look. Blair's mother sniffed and decided to let it slide.

"Next time, get Dorota to show you around. And no closed doors."

"Yes, ma'am."

"Blair will see you out." Blair nearly ran to the elevator, Chuck following nonchalantly behind.

"That's the second time I've saved your ass in one day. You owe me." He gave her a wolfish grin.

"Aw, go screw!" she replied, but she could hardly keep the smile off her face.

"Just so you know, I always come to collect," he yelled, as the doors slid closed.

"Blair." She had just begun to head back to her room, but turned around at her mother's call.

"Yes, Mother."

"A little advice. Charles Bass is a rather unorthodox choice, but a very wealthy choice, all the same. However, if you're going to play the two of them, I suggest you pick one before you lose them both." Blair's mouth fell open.

"Don't make that face, Blair. It's not becoming."

"Yes, Mother, of course, I just—it just—I'm not stuck on Chuck." Her mother raised an eyebrow in disbelief.

"Oh, please. The way you look at each other."

"We're just friends." Blair crossed her arms. Why did she have to explain herself?

"Very well, then. You may go." Blair walked away, feeling slightly nauseous and very confused.

"Dorota!" called Mrs. Waldorf.

"Yes, ma'am."

"Get Bart Bass on the phone. I'm sure Waldorf Designs can arrange something with Bass Industries. Something very beneficial." The machinery in her brain was already hard at work. Blair may not end up with the Vanderbilt ring on her finger, but ending up the wife of a billionaire might just be the next best thing.