Gossip girl

"Upper East Siders know that sometimes you have to take risks to get what you want. A bold move can catapult you to the top… or send you crashing down. So, who's ready to play? XOXO, Gossip Girl."

---

Morning at the Jain Penthouse – A Business and a Bet

I started my morning the way I always did—with a fresh espresso and a check-in on my family's investment firm. Jain Capital had been making quiet but steady moves, using my knowledge of the future to secure key positions in growing markets. Nothing too big, nothing too fast. Just enough to stay ahead without drawing attention.

Today's focus? Tech startups.

I had my assistant prepare a report on a small but promising company that would soon revolutionize e-commerce. Nobody in the market was paying attention to them yet. But in a few years? They'd be a gold mine.

As I finished reviewing my notes, my phone buzzed.

Chuck: Brunch at The Palace. Be there.

I smirked. Chuck Bass didn't invite people—he summoned them. But I had nothing better to do before school.

---

The Palace – A Game Begins

Brunch at The Palace was exactly what you'd expect from Chuck—endless mimosas, perfectly cooked eggs, and a table full of the elite.

"Gentlemen," Chuck greeted as I slid into the booth across from him and Nate.

"Morning," I said, grabbing a coffee.

Nate looked distracted, stirring his drink absently. Chuck, on the other hand, was in his usual smug mood.

"So," he drawled. "I hear Little J wants to be a big deal."

I raised an eyebrow. Jenny Humphrey. Serena's unofficial protégé and Dan's little sister.

"What about her?" I asked.

Chuck leaned back. "She's getting desperate to prove she belongs in our world."

I smirked. "That's not new."

Jenny had been trying to claw her way into Blair's social circle since day one. She was ambitious, I'd give her that. But ambition in our world was dangerous.

Nate sighed. "Blair's been pushing her into all these little games. She's going to get eaten alive."

Chuck grinned. "Or she'll adapt."

I glanced at my phone, a Gossip Girl blast lighting up the screen.

"Spotted: Little J playing with the big kids. But is she ready for the stakes? Careful, Jenny. The higher you climb, the harder you fall. XOXO, Gossip Girl."

Chuck laughed. "See? Even Gossip Girl knows this is a disaster waiting to happen."

I took a sip of my coffee. "Then let's see how far she's willing to go."

Because if there was one thing I knew about the Upper East Side—it was that people only revealed who they truly were when the stakes were high.

---

Jenny's First Real Test

That night, Blair and her clique dragged Jenny into their latest game: truth or dare. But in our world, dares weren't harmless.

The challenge? Sneak into a high-end boutique after hours and steal a dress.

Reckless. Stupid. Exactly the kind of thing that separated the weak from the elite.

I found out about it from Chuck, who was practically giddy with anticipation.

"This is going to be spectacular," he said.

I watched Jenny from a distance as she hesitated outside the store, Blair and the others egging her on.

"This is insane," Nate muttered beside me. "She's going to get caught."

"She's trying to prove herself," I said. "And Blair's watching."

Nate frowned. "You think she'll do it?"

I studied Jenny. She was nervous, but there was something in her eyes—determination.

"She wants this," I murmured.

And sure enough, Jenny took a deep breath, then slipped inside.

Chuck grinned. "Looks like Little J's got a backbone after all."

I wasn't so sure. Because ambition without caution? That led to disaster.

---

Dan and Serena – A Different Kind of Dare

Meanwhile, Dan and Serena were on their first official date. I had no doubt he was overthinking every second of it.

When I ran into him the next day, he looked surprisingly relaxed.

"How'd it go?" I asked.

Dan smiled. "Actually? Pretty great."

I smirked. "So you didn't completely embarrass yourself?"

He rolled his eyes. "No, but I did get roped into some ridiculous game at an Upper East Side party."

"Let me guess—Blair's crowd?"

Dan nodded. "They dared Serena to kiss someone in the room."

I raised an eyebrow. "And?"

Dan sighed. "She kissed me."

I laughed. "That sounds like a win."

Dan hesitated. "Yeah, but… I don't know. This world—your world—it's full of these little tests. Like people are always watching, waiting for someone to screw up."

I nodded. "That's because they are."

Dan frowned. "That doesn't bother you?"

I shrugged. "I grew up in it. You didn't."

Dan exhaled. "Yeah. I'm starting to see the difference."

He would learn. Or he'd get crushed.

---

The Fallout – And a Warning

Jenny got away with the dress—barely. But Blair wasn't done with her yet.

The next day, I found Jenny sitting alone on the Met steps, looking exhausted.

"You look like you've been through hell," I said, taking a seat beside her.

She gave a weak smile. "That obvious?"

I nodded. "You got what you wanted, though. You're in."

Jenny looked away. "For now."

I studied her. She was still naive enough to believe this was just about friendship. That Blair would ever truly accept her.

"Let me give you some advice," I said. "Blair doesn't pick friends. She picks people she can use."

Jenny swallowed. "I can handle it."

I smirked. "We'll see."

Because in our world, people either adapted—or they broke.

---

Final Gossip Girl Blast

"Dares have been played, secrets have been made. But in this game, the real winners are the ones who know when to fold. Careful, J. You might think you're climbing—but all it takes is one wrong step to send you tumbling down. XOXO, Gossip Girl."

I glanced at my phone and smirked.

This world thrived on chaos. And I was just getting started.