At the Empire Hotel bar.
"Come on, sis. I need you to focus."
Serena always got a bit too relaxed when she drank scotch—it made her brain a bit woozy, her body loose-limbed—but it seemed to have the opposite effect on Chuck. He was sitting with perfect posture, tracing the condensation on the bar with a finger. From the intense look in his eyes she knew that his mind was working programmatically—generating a plot, calculating its outcome, rejecting it, and moving on to the next. She, on the other hand, was having trouble thinking at all. Seeing Dan and Blair together was so outside the realm of belief—so contrary to everything she knew and loved—so deeply, horribly wrong—she felt like her entire world had gone topsy-turvy, and nothing mattered or made any sense any more.
"I'm sorry, Chuck," she said, rubbing her eyes. "I'm just so out of it."
"Let me remind you that we share a common objective," Chuck said. "We must destroy this unholy union as soon as humanly possible."
"Trust me, I couldn't agree with you more," Serena morosely replied. She tilted her glass, and drained it.
"So help me out here. You've barely said a word tonight. I know you're no Blair Waldorf, but you're not exactly a dilettante when it comes to the art of scheming. All you've done is shoot down my ideas. So please. Try to contribute."
"Okay," Serena said. "Maybe…we should take a psychological approach." As soon as the words were out of her mouth, she realized that she had no idea what she was talking about.
"What do you mean?" Chuck asked.
"Well— Her mind raced. If only there were an Idiot's Guide to breaking up a couple. A guide. A book. Suddenly she remembered her reading for last week's literature class. Othello. "We try to figure out how we should make them feel—so that they lose interest in each other. That's what we want, right?"
Chuck was quiet for a moment, and then he nodded several times. "That sounds really good, actually."
"Thanks," Serena said, a little surprised at the praise.
"I said it sounds good, sis, but that's not enough. The question is, how do we need to make them feel so that they realize their little experiment needs to end. Immediately."
"Well, we need to figure out how to make them feel, you know, angry. Jealous. Disgusted with each other." Serena thought about Othello. He was insecure about the color of his skin, his place in Venetian society, and, most of all, his beautiful young wife. All Iago had to do was whisper a rumor into his ear. "The question we need to answer is—how are they weak?"
Chuck looked at her, wide-eyed. "Impressive strategy, sis. Have you been taking a business class or something?"
"No. Elizabethan tragedy."
Chuck stared at her for a beat. "Okay. Profiles. Blair."
"Well, Blair's in a transitional period right now. She's on this whole powerful woman kick. She wants…to reinvent herself. To be independent. So…maybe she doesn't feel as close to us anymore. The question is, how to make her realize—"
"—that that's not a good thing," Chuck finished.
"That she needs us," Serena said, looking into his eyes. "Not Dan."
"Perfect," Chuck said, refilling his glass. "What about Humphrey?"
"Dan…you know, I think he's still a bit pissed at me. For…not choosing him."
"I thought you did choose him."
"I did," she insisted, "but then the whole Ben thing got in the way. I don't know. Maybe he went after Blair to get back at me."
"I don't get it. They always loathed each other," Chuck said. "But it was nothing like the hatred that Blair and I shared, you know, the kind that ends in explosive, mind-bending sex—"
Serena wrinkled her nose.
"It was the hatred of people from two different worlds and absolutely no desire to build a bridge between them," Chuck continued. "People who hate everything that the other person represents." He sipped his scotch. "If Dan Humphrey is going after Blair Waldorf, he must have been doing some reinventing of late, too."
"Yeah, he reinvented himself, all right," Serena said, "into a total asshole. You wouldn't believe what a jerk he was to Ben."
Chuck's eyes lit up. "We have to make him disgusted with the person he's become," he said.
Serena's jaw dropped. "Chuck, that's really good. You're right. But…how do we do that?"
"I've almost got it," Chuck said. "Who does he hate more than anyone?"
"Well, no offense," Serena said. "But…you. Obviously."
"And he's going after my ex," Chuck continued. "So what does that make him?" His voice trailed off, and then he looked at Serena with wide eyes. "Oh my God. Serena," he said. "I've got it."
"What?"
"It's like it was predetermined by a higher power," Chuck said in an awestruck tone. "Something out there knew we would find ourselves in this situation one day. It's…providential. It's miraculous."
"What are you talking about?"
"It's the perfect fucking plan."
"Chuck, come on," Serena said. "Tell me. I'm on the edge of my seat."
To her surprise, he leaned in towards her, reached out his hand and began to stroke the underside of her wrist. "Do you happen to remember," he purred, "what you were doing five years ago tonight?"
"Uh, no," Serena said. "Chuck, come on. What does that have to do with anything?"
"Think a little harder," Chuck said. "Try to remember…the special times we've shared."
Her eyes widened. "No."
"Yes."
"That can't be right. No. How would you even remember that?"
"Did you really think that I could ever forget the sensation of Serena van der Woodsen's thighs against the sides of my head?" Chuck said. "Her knees wrapped around my shoulders? Her face in ecstasy? On the contrary. For years I cherished it as one of my choicest sexual memories."
"Eww, Chuck!"
"Look, sis, relax. I haven't turned to it in my...hour of need for some time now. At least not since you officially became my sister. But that doesn't mean that I developed selective amnesia."
"Well, you should have. We had a solemn vow to never, ever, speak of that night again."
"And it's a good thing that we didn't," Chuck said. "Because now is the perfect time to tell the world about it."
Serena stood up. He grabbed her arm. "Look, hear me out," he said.
"There is no fucking way we're sending this to Gossip Girl, Chuck."
"Listen," he wheedled. "It's perfect. We all know how Gossip Girl gets her kicks."
"Uh, by ruining people's lives?"
"By creating the biggest sensation possible. That's why she sometimes withholds information in order to release it at a more strategic time. Now, if we drop this now—it won't look like a response to the current situation."
"It'll look like one of Gossip Girl's productions," Serena said slowly.
"Right," Chuck said. "And what's more spectacular than the five-year anniversary of Serena van der Woodsen's first orgasm?"
"First of all, you're a pig." Serena said. But she was already sitting back down again, her mind beginning to whirr. "But you're right. She won't be able to resist it."
Chuck smiled.
"And you're right about the date, too," Serena continued. "No one will think that we're the ones who leaked it."
"Mm-mm," Chuck said, wagging a finger. "Dan will. That's why I'm going to stage a run-in with him. He'll accuse me of making up the rumor, I'll inform him that it's true…and then I'll take it one step further."
"How?"
"Maybe you haven't noticed, but Dan Humphrey has something of a pattern when it comes to women. Georgina, Vanessa, Blair…and you."
"All women you've slept with."
"And why do you think that is?"
"Um, because you're such manwhore that it's pretty much impossible to find anyone on the Upper East Side who you haven't slept with?"
"No—well, yes," Chuck said, "but that's not the point. I'll tell him that he's unconsciously obsessed with me. That he wants to be Chuck Bass. And that's why he's going after Blair."
"Chuck, that's ridiculous."
"Oh, I agree. But who cares? Once he hears that Chuck Bass slept with the love of his life, he won't be able to think straight. Trust me—a fragile mental state combined with circumstantial evidence is a compelling combination. Even if it weren't true, planting a seed of doubt would be enough for our purposes."
"Yeah—just like Othello!" Serena said. "That's totally what I've been thinking about this entire time."
"What are the hell are talking about?"
Serena stared at him for a beat. "Wow. You really did skip a lot English class to smoke up in the courtyard when you were at St. Jude's, didn't you?"
Chuck shot her a disgruntled look. "Anyways," he said, "Humphrey will pretend not to believe me, and then he'll go to you."
"And I'll confirm?"
"Yes. And from that moment onwards, every time he looks at Blair—all he'll see is me." He drained his glass.
"What about Blair?" Serena asked. "How do we handle her?"
Chuck frowned and reached again for the decanter. "She'll be upset."
"I'll reassure her, tell her it's ancient history—"
"—And that you understand why she's upset," Chuck finished.
"She'll be upset at me for hooking up with you," Serena said, "so she'll feel guilty that she hooked up with Dan."
Chuck nodded. "And hopefully she'll finally realize who she really wants to be with. Me."
"You're right," Serena said. "It really is the perfect plan."
"What about collateral damage?"
"Um, our reputations?"
"Already shot to hell," he returned.
Serena sighed. "True."
"The only thing I'm worried about is Lily," Chuck said, frowning. "Does she still read Gossip Girl?"
"No, giving it up was her New Year's resolution this year," Serena said with a laugh. "But Erik reads it. He'll be weirded out for sure."
"You think he'll tell her?"
"I dunno. Maybe."
"You think they'll get over it?"
"Well, it's not like they haven't had plenty of practice," Serena said. "I mean, hello—me and Dan? Also stepsiblings."
They sat in silence for a moment.
"Then it's settled," Chuck said.
"Yep."
"You want to do the honors?" he asked.
Serena whipped out her phone, tucked a strand of blond hair behind her ear, and took a deep breath. Her thumbs danced over the keypad, and then hovered over the send button.
"Do you want me to see it through?" Chuck asked.
"No," Serena said. She pushed the button.
"To love and happiness forever," Chuck said, lifting his glass.
"Love and happiness forever," Serena repeated, clinking her glass against his.
They drank and set their glasses down on the bar, and they sat for a few moments in silence.
Then they heard the familiar chime. Even though they were expecting it, it still made their stomachs drop, their hearts thump in their chests. Serena fumbled in her pocket for her phone.
"I knew she wouldn't be able to wait," Chuck crowed. "What does it say?"
Serena held out her phone between them. There were their yearbook portraits from sophomore year, photoshopped together—Serena wearing eyeliner, her mouth open in a laughing grin, Chuck with artfully tousled hair, smirking.
"God, we look so young," Serena said, a little dismayed.
Underneath the picture was the blast:
Gather 'round, children—have I got a juicy gossip blast from the past for you.
It's no secret that Serena van der Woodsen likes to keep it in the family, but I bet none of you knew about the intimate evening she shared with her stepbrother five years ago to the day. Oh no—I'm not talking about Dan Humphrey. I'm talking about her other stepbrother.
Turns out the infamous Chuck Bass bedded our favorite blonde beauty when they were only fifteen years old. And while he didn't get her V-card, we hear he was the first—the first to see her O-face, that is. Rumor has it the bass is quite the expert when it comes to swimming downstream—if you know what I mean.
Ta-ta, children. You know you love me.
xoxo,
Gossip Girl
Chuck stared at the blast for a few seconds. "It's perfect," he declared. "Even better than I thought it would be."
Serena didn't say anything.
"What, you don't like it?" he asked. "I like it."
"Of course you like it. You come off like Casanova. I sound like a psycho-slut who likes to sleep with my stepbrothers."
"Well, she did call you a 'blonde beauty,'" Chuck said. "That's good—right?"
"Hm."
"I think it's great. Humphrey is going to lose his shit," Chuck said. His eyes rescanned the last few lines of the post. "I like that 'swimming downstream' thing," he added. "That's pretty clever."
"You know," Serena said, "I always wonder when she's going to run out of bass puns. But they just keep coming, don't they?"
More chapters on their way. In the meantime, I'd love your thoughts.