A/N: This chapter is way longer than the last one and not realistic at all. But screw you because headcanons trump all.
Summer 2012, Chapter 2: The Designer
"Damn it!"
Chuck turned into his hall in time to see a woman in front of the door next to Blair's drop the dress bags that had been dangling precariously on her luggage cart. The dresses had caught some shoeboxes and jewelry cases, and the floor was now a litter of Louboutins and glitter.
"Here, let me." Chuck ran up and started handing the woman various items.
"Ugh, thanks. I'm such a - " She turned her head toward him. "Chuck?"
"Jenny?"
Blair looked up from the samples she'd been staring at for at least an hour, completely exasperated. "Mother, none of these designers are right."
"They can't all be that bad," Eleanor Waldorf replied from her drawing table.
"Some of them are awful, yeah. There are a bunch here that're, you know...great. The dresses are beautiful. I'd love to own a lot of them. It's just that they're not the right fit for the company."
"Well, darling, you'll have to choose one of them. I'm sure you can find one designer that would be acceptable."
"That's it, though. All of these designs are adequate. But I'm not looking for adequate. I'm looking for extraordinary." Blair crossed the room and looked over Eleanor's shoulder. "Oh, Mother. That's beautiful. What's it for?"
"Actually, this is one of Jenny Humphrey's pieces. She doesn't think it's her finest work but it has potential, and she asked me to take a look at it."
Blair stared at the dress on Eleanor's table. "Jenny Humphrey," she whispered. "She's perfect."
"Blair, you hate Jenny. How would the two of you work together?"
"I can handle working with her if she keeps making things like this. Besides, if Chuck and Jack can do it..."
Eleanor smiled. "If you're sure the two of you can work together, then I think she's a wise choice."
"I'm going to call her." Blair pulled out her phone and walked into the empty kitchen across the hall.
Jenny answered on the second ring. "Um, why are you calling me? You told me by proxy that I could spend the summer in the city as long as Erik keeps an eye on me."
"Look, I know we hate each other, but hear me out." Blair took a deep breath. "I saw the dress you sent my mom. The white sleeveless one."
"Oh. Well, what'd you think of it?"
"I don't think it was your finest work...but it was still one of the most amazing dresses I've ever seen."
"Thanks, I guess. But, um, you're calling me about one of my more mediocre designs for, what, a chat?"
"I don't know if Eleanor told you or if word travels quickly in the fashion world or something, but I'm guessing you've heard by now that my mother is stepping down from Waldorf Designs and I'm taking her place as CEO."
"Yeah, Eleanor told me awhile ago. Why?"
"Because, Jenny Humphrey, I'm not a designer. The plan was for me to officially be the company's titleholder and business manager, I would hire a designer to replace Eleanor, and we would be fifty-fifty shareholders. Kind of like you and what's-her-name, but with more class."
"Agnes. Seriously, though, Blair, I'm supposed to leave to go to JFK in, like, thirty seconds, so get to the point."
"I've spent the summer looking at hundreds of designers' portfolios. Lots of them were good, but they're just not the right fit for the Eleanor Waldorf name. Then I saw your dress a few minutes ago and it hit me: you're the perfect person to replace my mother."
Jenny was silent for a moment, then she said, "What?"
"Jennifer Tallulah Humphrey, will you be the new Eleanor Waldorf?"
"You want to work with me? Are you serious? Or is Ashton about to jump out at me from behind Lily's couch?"
"You know how hard it is for me to say this, but I need you."
"Um, then, duh. Of course I'll take them job."
"Fantastic!" Blair exclaimed. "Is there any way you could come out to Paris for the summer instead of staying in New York?"
"I'm actually supposed to be leaving to visit Dan in Italy right now, but you know what, screw Dan."
"Great. I'm booking you a flight as we speak. There's one that leaves from JFK in two hours."
"Cool. I guess I'll, you know, see you?"
"It's gonna be kind of late by the time you get here, so I'm just going to send a car to get you at the airport. Bring every clothing item you own. I'll pay you back for baggage."
"Blair - " But the line had already gone dead.
"Jenny?"
"Oh my God! Hey!" Jenny exclaimed. They stood there awkwardly for a second, until Jenny finally said, "So, can I, like, have a hug or something?"
Chuck laughed and they hugged.
"So, what're you doing here?" Jenny asked. "Are you and Blair finally, like - ?"
"Kind of, but no, not really. Blair's stalking me, actually, which is an interesting change of pace." A smile twitched at the corner of his lips. "What are you doing here? Isn't Blair going to kill you or something?"
"Hopefully not; she invited me here."
Suddenly, the door in front of them flew open, and Blair stood there in a Batman t-shirt and faded camo sweats. "Jenny, is that you - oh, hey, Chuck. Good, less explaining for me. I'm sure Chuck's already told you about my modified stalking."
"Yup." Jenny replied.
"Chuck was standing there smirking. "Nice outfit, Waldorf."
"You, too, minus the sarcasm." Chuck looked dashing as always, his yellow bowtie and pocket square sitting up jauntily. "This is what us single ladies wear to bed."
"Am I ever going to get an explanation for this?" he asked, gesturing between Blair and Jenny.
"You'll get your explanation as soon as you've had your few months." Blair smiled innocently at him.
He grinned. "Good night, Blair. Jenny, nice to see you."
"Night, Chuck," they chorused. Blair turned to Jenny. "Do you want to drop your stuff in your room and then we can talk?"
Jenny nodded and pulled her key card out of her pocket, opening her door.
Five minutes late, they were sitting in the armchairs in Blair's suite.
"So how'd you stomach calling me?" Jenny asked, taking a sip of her cream- and sugar-laden coffee.
"Honestly, it wasn't as hard as I thought it would be. I haven't really been mad at you since...if I had to pick an exact moment, it would be when you came to my house and told me everything about you, Juliet, and Vanessa. I mean, facing my wrath by even coming to my place was brave enough, but to confess your involvement in something that ended in my best friend being hospitalized? That scored you major points. Plus when I asked you to go double-agent and you said no? I'm not going to lie, I admired you so much then." She got quiet for a minute, then continued. "My mom told me you got into Parsons last year. You should have told me. I would've let you go."
"Maybe," Jenny replied, "but I wouldn't have let me go. The two years out of the city were good for me. So good that I think i may actually be able to come back now."
"Well, that's perfect, because we'll need to work together all year. Eleanor's still going to be the officially head for another year, so that I can graduate, and then it's ours. But it's still going to be a lot of work. I'll need you in New York." They sat in silence for a minute, sipping their coffee, until Blair said, "I'm really going to try to make this not awkward."
"Yeah, I don't think that's going to be possible. There's too much bad blood for us to not be awkward, and way too much history, even though we may not have the very core of our beings filled with hatred. Which is a shame, you know, but as Penelope once said to me, 'This is about fashion, not friendship.'"
Blair laughed. "It's a tragedy, though, because I feel like if I didn't hate you, I would genuinely like you."
They both chuckled. Then Jenny said, "So what's the story with you and Chuck?"
Blair rolled her eyes. "Oh, my God. Well, the last year happened. I'm sure you heard about a lot of it."
"Jesus Christ. Between Erik and Dan, it was all I heard about. Serena kept ranting about you and your drama to Erik. It was funny because she would just show up at Erik's dorm room and he secretly put her on speaker so that I could hear it firsthand. But then by like the fourth time she caught on and that sucked. But yeah, I heard."
Blair was laughing really hard by then. "Yeah, so Chuck's kind of been chasing me all year, but a bunch of crap went down, mostly on my end, and then Bart Bass magically came back from the dead and convinced Chuck that I suck ten minutes before I went to tell him I was ready to actually be with him. Long story short, he shot me down, I stalked him down to a Monte Carlo casino with Jack Bass' help, and we talked. So yeah, I said some stuff. We decided that we're taking some time this summer so that he can reestablish himself in the business world, and he's going to call when he's ready. In the meantime, I'm on modified stalk mode."
"So what you're saying," Jenny said, "is that Chuck Bass is available and living next door? 'Cuz in that case, I gotta go."
Blair threw a pillow at her. "Hush, Little J."
"But seriously. What if he doesn't call and it turns into the last few years all over again?"
"He'll call." Blair replied confidently. "Chuck's reliable now. Much more reliable than I've ever been."
"But seriously, what's your relationship status right now? I'm curious and I'll have to report back to Erik, since he's lost Serena as his Chair news source."
"Chair?"
"Oh, yeah. Do you not know about this? There's a whole underground betting ring in Manhattan, wherein people bet on who you're going to ultimately end up with, and Erik has $30,000 on you and Chuck."
"Oh my God. Why do I not know about this?"
"Trust me, it's crazy. You don't want to know. There's all kinds of crazy Blair couples people bet on."
"Who else that I know bets on this, other than Erik?"
"Chuck has twelve dollars on the two of you. Erik saw him and Nate there once and spied on them. Nate has $20,000 on it, but Chuck doesn't know; he thought Nate was just there for support. Serena doesn't know. There are other people, but yeah. It's a huge thing."
"Chuck only has twelve dollars? That's not very confident."
"Well, he could have hundreds of thousands on it, but then there would always be the chance of not knowing whether he's chasing you because he loves you or for the money."
"Good point. Twelve dollars, though."
Jenny looked at the clock. "Oh, wow. When did it get to be one in the morning?"
"Time change. You'll get used to it. I'm exhausted, though, so I'll have to call it a night. We can go into the studio tomorrow and hang out with my mom."
"Fabulous." Jenny stood up. "I think I'll watch TV or something in my room."
"Cool. Good night."