Picking Up Girls With My Pickup System-Chapter 39: Derek Makes His Move.

The countdown didn’t slow just because Kent made a choice.

If anything, it felt like the System turned the screws tighter.

[Countdown: 21h 12m]

The numbers glowed faintly in the corner of his vision, a constant drumbeat in his skull. Every time he blinked, every time he exhaled, they were waiting for him.

Morning sunlight filtered through the Ridgeway windows like nothing had changed, but to Kent, the halls felt like a hunting ground. Every laugh sounded like it had his name in it. Every glance lingered too long.

Derek hadn’t lifted a fist. He didn’t need to. His whispers were knives, and the school was bleeding out belief in Kent one rumor at a time.

The System confirmed the rot:

[Reputation: 23%]

[Hostility: 52%]

[Status Effect: Social Isolation II – Stigma Active]

Kent walked with his head down, but the murmurs still reached him.

"Did you hear? He got caught hacking into the office files."

"No way, that’s a felony."

"My cousin swears he has dirt on teachers too. Blackmail. Totally explains why he hasn’t been expelled yet."

Jake was waiting by his locker, jittery as always. His hoodie hung crooked, his eyes bloodshot from another sleepless night. He barely let Kent reach for his books before snapping, "Tell me you’ve got a plan. Please. Anything."

Kent shoved his binder into his bag. "We stick to the trap."

Jake groaned, dragging a hand through his hair. "The trap. Right. Where you dangle yourself in front of Derek like a slab of steak. Genius. Totally not suicide."

Before Kent could respond, Mia appeared, moving like a shadow between students. She didn’t even glance at Jake. Her eyes fixed on Kent. "Derek’s spreading the file rumor harder. Three people mentioned it to me in first period alone. If he pushes it any further, teachers will start hearing."

Kent’s stomach clenched. "Then we need to make him overplay it. Fast."

Samir joined them, calm as always, though the faint tension in his jaw betrayed him. "The key is control. Derek wants you isolated. He is building a frame where any denial looks like desperation. We must design a stage where his arrogance compels him to reveal too much."

Jake muttered, "Great. Except right now it looks like he’s already winning without lifting a finger."

The System pulsed:

[Group Unity: 58% – Strained]

[Warning: Infighting Risk High]

Kent exhaled, forcing the weight down. They couldn’t crack now. Not with the entire school watching.

******

Derek made his first open strike.

It happened halfway through class, when the teacher turned to scrawl equations across the board.

Derek’s voice carried from the back row. Not loud—but just enough.

"...yeah, weird how someone broke into the office records last week."

The room stilled. Pens stopped scratching. Heads tilted.

Derek chuckled low, casual. "Must’ve been someone desperate. Y’know, trying to dig up dirt to stay relevant."

Whispers prickled across the classroom. Kent kept his eyes locked on his notebook, but his ears burned.

The teacher half-turned. "Mr. Lorn. Is there something you’d like to share with the class?"

Derek raised both hands in mock innocence, grin sharp as glass. "Just saying—kinda crazy, right? Imagine someone sneaking into files to hold stuff over people. Makes you wonder what kind of person would even do that."

A few kids snickered. More leaned back in their seats, eyes drifting toward Kent like magnets.

The System delivered its verdict:

[Reputation Check Failed]

[Student Support: 23% → 19%]

[Hostility: Rising]

Kent didn’t move. Didn’t blink. He felt Derek’s gaze burning into the back of his skull, waiting for him to snap, to lash out, to prove the rumors right.

But Kent stayed still, jaw locked, pen frozen above the paper.

That was when Derek leaned forward, voice dropping just enough for Kent alone to hear:

"Tick-tock, Gilbert."

The words crawled under his skin like acid.

By the time lunch hit, Kent’s nerves were stretched so thin he thought he’d snap if one more person whispered his name.

The cafeteria felt different now. Not like a battlefield. More like a trial. Every table was the jury box. Heads turned when he entered, whispers rippling outward like waves. Phones tilted ever so slightly, screens glowing as they captured his every move.

Jake muttered under his breath, "This is a circus. They’re literally waiting for you to trip. Dude, I swear—half of them are live-streaming this."

Kent scanned the room. Mia was already seated at their usual table, her expression unreadable, Emily beside her with her ever-present notebook, pen tapping steadily against the page. Samir sat across from them, calm but focused, like he was calculating outcomes of a chess match.

They weren’t the ones Kent was worried about.

It was Derek.

He sat at the far end of the cafeteria, surrounded by his usual pack. His grin was razor sharp, his laugh just loud enough to cut through the noise. And when his eyes met Kent’s across the room, he didn’t look away.

The System pulsed:

[Critical Rival Encounter Approaching]

[Probability of Confrontation: 86%]

Kent slid into his seat. His tray remained untouched. His hands trembled just slightly under the table, and he clenched them into fists to hide it.

Emily leaned closer, voice low. "He’s coming. You know that, right?"

Kent swallowed. "Then we make him walk into the trap."

Jake snorted. "Trap? Dude, we don’t even have a trap yet. All we’ve got is a ticking clock and the genius plan of ’let Derek punch you in the soul until he screws up.’"

Samir’s tone was cool. "Correction. The trap is Kent. All that remains is the stage."

"Awesome," Jake muttered, raking his hands through his hair. "So we’re banking on Gilbert’s face being bait enough to piss Derek into making a mistake. Love it. Totally love it."

The words had barely left his mouth when the cafeteria fell into sudden hush.

Because Derek was moving.

He cut across the room like he owned it, his entourage trailing behind him. His smirk grew with every step. Every table turned to watch. The whispers sharpened into gleeful static.

Jake cursed under his breath. "Here we go..."

Derek stopped at their table. His shadow fell over Kent’s tray.

"Well, well. Gilbert the ghost." His voice was smooth, casual, dripping with mockery. "Heard you’ve been real busy. Digging through other people’s lives. Blackmailing. Sneaking. Real stand-up citizen."

Laughter rippled behind him. Phones tilted closer.

Kent didn’t move. His pulse thundered. The System pulsed:

[Decision Point: Respond]

Options:

Deny → Risk: Appears desperate.

Stay Silent → Risk: Appears guilty.

Counterattack Verbally → Risk: Escalation.

Jake tensed beside him, whispering furiously, "Don’t just sit there! Say something—anything—"

Kent raised his eyes slowly, meeting Derek’s smirk. His voice came out low, steady.

"You really like hearing yourself talk, don’t you?"

The cafeteria reacted instantly—snickers, gasps, a few cheers.

Derek’s grin flickered, but only for a heartbeat. Then he leaned closer, his face inches from Kent’s. His voice dropped to a venomous whisper that only their table could hear.

"You’re dead, Gilbert. Not today. But soon. Everyone’s gonna see you for what you are—a fraud. And when they do, no system’s gonna save you."

The System pulsed viciously in Kent’s vision:

[Rival Escalation Detected]

Derek is preparing a major move.

Probability of Entrapment Attempt within 24h: 94%

Derek straightened, flashing that grin again, and sauntered off with his pack.

The whispers exploded behind him like fireworks.

Kent’s chest heaved, but he forced his hands to stay flat against the table. Emily’s pen tapped faster, her voice sharp. "He’s setting up. That wasn’t just talk—he’s telegraphing something. Big."

Mia finally spoke, her tone calm, certain. "Then we force him to act faster."

Jake groaned. "And how the hell do we do that? Put a target on Kent’s back and hope Derek bites sooner?"

Emily’s eyes flicked to Kent. "Exactly."

The System pulsed:

[Entrapment Path Progression: Phase Two]

Next Step: Stage the Perfect Opening.

Kent swallowed hard. His throat was dry as sandpaper.

He was the bait. And Derek was circling closer.

The basement smelled faintly of dust and old carpet, the single lamp overhead throwing their shadows long against the walls.

Kent sat hunched forward, elbows on his knees, staring at the log in its taped sleeve on the table. It hadn’t moved, but it felt heavier with every second the System’s countdown ticked in his head.

[Time Remaining: 19h 06m]

Emily clicked her pen against her notebook, each sound like a gavel in the silence. She had already drawn another flowchart, arrows and boxes sprawled across the page like the wiring of a bomb.

"We don’t get to wait for Derek to pick the stage," she said, her tone sharp. "If he chooses, he controls the fallout. We need to create the stage ourselves. Somewhere public. Somewhere undeniable."

Jake groaned, throwing himself against the back of the couch. "So what? You want us to just plant Kent in the middle of a spotlight and pray Derek takes the bait? That’s not a plan, that’s assisted suicide."

Mia’s voice cut through, soft but absolute. "Public is the only option. If Derek moves in the dark, he controls the narrative. If he moves in the light, he exposes himself."

Samir adjusted his glasses. "Correct. The key is to present Derek with an opportunity so tempting he cannot resist—yet structured so his strike leaves evidence."

Kent finally looked up. His voice was hoarse. "So what’s that opportunity?"

Emily tapped her notebook. "A crack in the armor. We make Derek believe you’re about to break. That you’re isolated. Weak. Ready to confess something."

Jake sat up fast, disbelief etched across his face. "You mean pretend Kent’s about to spill? Like, stage a fake confession?"

"Exactly," Emily said.

The System pulsed in Kent’s vision:

[Entrapment Path: Sub-Option Unlocked]

Fake Confession

Fake Betrayal by Ally

Accidental Exposure Setup

Mia tilted her head slightly. "Fake confession is dangerous. He might wait. Fake betrayal forces him to act faster."

Jake swore under his breath. "Or it forces him to gut us in the open and leave us bleeding."

Samir’s tone was level, detached. "Accidental exposure is cleaner. A ’leak.’ Something Derek thinks he can exploit before anyone else sees it. He would rush to seize the advantage."

Emily nodded once. "Then that’s our strongest play."

Kent rubbed his temples. "So what—you want me to stage something? Like a fake recording or...?"

Emily’s eyes locked on him. "A message. Something ’slipped.’ Something Derek will believe you didn’t want out—but that he can’t resist twisting. He’ll try to weaponize it. And that’s when we catch him."

The System chimed:

[Quest Update: Stage the Leak]

Requirement: Plant falsified bait evidence before deadline.

Time Remaining: 18h 42m

Jake buried his face in his hands. "This is insane. We’re literally manufacturing our own blackmail just so Derek steals it."

Mia’s calm voice broke the silence. "And when he does, we bury him with proof."

Kent leaned back, heart pounding so hard he thought it might crack his ribs. He could see it all playing out—the cafeteria whispers, Derek’s smirk, the trap slowly closing.

He whispered, almost to himself: "So we fake a leak. And wait for the wolf to bite."

The System pulsed, brutal and clear:

[Entrapment Play: Phase Two Active]

Objective: Create Believable Bait File.

The room was silent, every pair of eyes fixed on Kent.

For the first time, he wasn’t just playing defense.

He was laying the snare.

The glow of Kent’s old desktop screen lit the basement like a stage spotlight. Lines of text scrolled as Emily typed, her expression taut, her pen tucked behind her ear.

Jake hovered behind her chair, fidgeting with the drawstring of his hoodie. "This feels so wrong, man. Like... we’re literally making fake evidence. That’s Derek-level dirty."

Emily didn’t look up. "It’s not fake evidence. It’s bait. There’s a difference."

Jake barked a short, humorless laugh. "Wow. Yeah, sure. We’re lying for justice. Totally different."

Mia, seated cross-legged on the floor, tilted her head. "Derek has already framed Kent with lies. This only forces him to reveal himself in pursuit of them. That’s not corruption. It’s strategy."

Samir adjusted his glasses, eyes reflecting the monitor’s light. "Correct. The distinction is intent and control. We’re not deceiving the innocent—we’re exposing the guilty. The moment Derek acts on this, he condemns himself."

Kent sat at the far end of the table, staring at his hands. His palms were damp, trembling despite how tightly he clenched them.

The System pulsed faintly:

[Moral Integrity Check: Strained]

[Leadership Stress: Rising]

He forced himself to speak. "What exactly are we making?"

Emily’s fingers flew across the keyboard, the clack of keys filling the silence. "A fabricated note. A draft of a ’confession.’ Something Kent supposedly typed out and saved, but never sent. We’ll plant it somewhere Derek can find it—on a decoy USB, maybe. Something too tempting for him to ignore."

Jake frowned. "And what does it say?"

Emily’s tone sharpened. "Enough to make him think Kent’s about to admit to blackmailing half the school. Enough to make him believe he’s won. But vague enough that Derek has to act fast to twist it before anyone else sees it."

She hit the enter key with a sharp tap. The screen blinked, and a block of text appeared, the draft confession.

Jake leaned closer, muttering as he read:

"I can’t hold it anymore. Derek’s right. I recorded things I shouldn’t have. I thought it was harmless at first, but now it’s out of control. If anyone finds out what I did, I’m finished. Maybe I deserve it. Maybe I should just come clean before he forces me to."

Jake’s face twisted. "Jesus. This is... brutal."

Mia’s voice was flat, clinical. "It is believable."

Samir nodded. "Psychologically precise. It frames Derek as both predator and liberator. He won’t resist using it."

Kent swallowed hard. Reading the words felt like staring into an open grave with his name etched on the headstone. It was too close. Too real.

His throat tightened. "If this leaks beyond Derek, I’m done."

Emily finally looked up at him, her expression unflinching. "It won’t. Because we’ll control it. The moment Derek touches it, we catch him in the act. He’ll try to parade it as truth, but we’ll have the metadata, the timestamps, the setup itself. He’ll be trapped."

Jake rubbed his face with both hands, groaning. "And if he doesn’t take the bait?"

Mia answered before Emily could. "Then Kent burns alone."

The basement fell into silence. The words hung in the air like a guillotine.

The System pulsed viciously:

[Risk Level: Severe]

[Reward Potential: Decisive Blow]

[Countdown: 17h 21m]

Kent forced himself to stand, pushing his chair back. His knees felt weak, but his voice was steady enough when he spoke.

"Do it. Save the file. Make the USB. If Derek wants me broken, let’s give him the perfect reason to overreach."

Emily’s fingers flew across the keyboard again, locking in the file, copying it to a small silver flash drive. She snapped it shut with a click, setting it on the table like it was a loaded weapon.

Samir leaned back, his calm tone almost eerie. "Now comes the harder part. Making sure Derek sees it—and thinks he’s stealing it."

Jake groaned again, dragging a hand through his hair. "Which means we have to fake a screw-up. Great. My favorite kind of plan: the kind where we hope our enemy buys that we’re idiots."

Emily closed the laptop with a sharp snap. "Then we’d better act convincingly."

The System chimed:

[Quest Progression: Bait Prepared]

Next Step: Stage the Leak]

Time Remaining: 16h 49m

Kent stared at the USB on the table, his reflection warped in its silver shell. It looked so small. So harmless. But if Emily was right, this was the noose Derek would wrap around his own throat.

He whispered, almost too soft for the others to hear:

"Please let this work."

The System pulsed, cold and merciless:

[Outcome Uncertain]

******

By the next morning, Ridgeway High felt like a powder keg waiting for a spark.

Kent sat through first period without hearing a single word. His notebook stayed blank, his pen unmoving. The System’s countdown throbbed at the edge of his vision like a second heartbeat:

[Time Remaining: 13h 12m]

Every tick of the clock dragged him closer to the moment Derek either fell... or Kent shattered.

At break, the group huddled by the far end of the library where no one went unless they needed the dusty shelves of reference books. The USB sat in Emily’s palm, its polished silver glinting like a knife.

Jake kept pacing the carpet, muttering under his breath. "This is insane. Totally insane. We’re gambling our lives on the assumption Derek’s too nosy to resist. What if he doesn’t even find the thing?"

"He will," Emily said, her voice clipped. "Because we’ll put it exactly where he expects us to slip."

Samir adjusted his glasses, his tone as calm as ever. "The psychology is sound. Derek thrives on weakness. If Kent ’accidentally’ leaves this behind, Derek will not see restraint as an option. He will act."

Mia leaned against the shelf, arms crossed. "Then the question is where. The wrong spot makes it obvious bait."

Emily placed the USB on the table between them. "His locker. Too controlled. His desk? Too visible. No—the most natural option is Kent’s bag. If Derek thinks he’s stealing it directly from Kent, the thrill doubles. He won’t resist."

Kent’s stomach twisted. "So I’m supposed to... what? Just walk around with this thing hanging out of my pocket like a neon sign that says ’Please rob me’?"

Emily’s gaze didn’t waver. "Yes."

Jake stopped pacing and stared at her. "That’s not a plan. That’s suicide."

"Not if we control the circumstances," Emily countered. "We’ll orchestrate it during lunch. Kent will ’forget’ to zip his bag. Derek will see the USB sticking out. He takes it, thinking he’s clever. But we’ll already be recording everything from three angles."

Mia’s voice was steady, almost eerily calm. "And if he suspects?"

Emily’s jaw tightened. "Then he doesn’t take it. And Kent burns anyway."

Silence slammed down.

The System pulsed mercilessly:

[Risk Level: Maximum]

[Group Unity: Strained]

Jake slammed his fist lightly against the shelf, voice cracking. "I hate this. I hate that we’re sitting here plotting like we’re spies while Derek just... smirks his way through the halls. This isn’t a plan—it’s a coin toss with someone’s life on the line!"

Samir’s gaze flicked to him, unshaken. "It is better than certain defeat. Derek has momentum. We have one chance to redirect it."

Jake snapped, "You sound like a robot! Do you even care what happens to Kent?"

For the first time, Samir’s voice sharpened. "That’s why I’m here."

The words hit like a slap, silencing Jake.

Kent forced himself to stand, his throat dry. His pulse hammered so loud he thought they could hear it.

"I’ll do it," he said. "If Derek wants to destroy me, then fine. Let’s give him the chance to try."

Emily’s eyes softened, just barely. "You’ll need to act convincingly careless. Nervousness will kill the setup."

Kent gave a hollow laugh. "I’ve been nervous for a week straight. Shouldn’t be hard to fake."

The System chimed:

[Quest Updated: Stage the Leak]

[Objective: Ensure Derek Notices USB]

Time Remaining: 12h 07m]

Jake dropped into a chair, burying his head in his hands. "God help us. We’re really doing this."

Emily slid the USB across the table toward Kent. Its smooth surface caught the dim library light as it stopped at his hand.

For a moment, he didn’t touch it. Couldn’t. The weight of it wasn’t plastic or metal—it was reputation, survival, the difference between triumph and annihilation.

Finally, he closed his fingers around it.

The noose was ready.

Now all they had to do was feed it to Derek.