Picking Up Girls With My Pickup System-Chapter 34: Midnight At The Old Gym.

Kent sat at his desk, the glow of his phone screen washing over his bruised face. The message pulsed at him like it carried its own heartbeat:

[We saw you stand up last night. You don’t have to face Derek alone. Meet us. Midnight. The old gym.]

His ribs ached every time he leaned forward. His lip stung where it had split. But it wasn’t the pain that left his hands trembling—it was the choice.

The System was merciless in its timing.

[New Quest Branch Unlocked: Unknown Allies or Greater Trap?]

[Objective: Decide whether to meet the sender.]

[Warning: Ambush Probability: 61%]

Kent muttered under his breath. "Sixty-one. Great. So... coin flip with extra knives."

The floor creaked behind him. Jake leaned against the doorframe, hair a mess from sprinting over after seeing the same message. He jabbed a finger at Kent’s phone. "Bro. That’s a setup if I’ve ever seen one."

"Or it isn’t," Kent countered, though his voice lacked conviction. "What if it’s... real? What if people actually want to help?"

Jake snorted. "People don’t just hand out loyalty cards, man. Especially not against Derek. He’s got the school wired tighter than the cafeteria Wi-Fi."

Kent rubbed his temples. His head was already pounding from the day’s whispers, the stares, the way Derek had loomed over him at lunch like a thundercloud waiting to break. Enjoy your fifteen minutes, Gilbert.

He didn’t want to admit it, but Derek wasn’t bluffing. Payback was coming. And maybe—just maybe—walking into the old gym tonight meant finding allies before Derek found a chance to corner him alone.

The window rattled. Mia slipped in like she owned the place, tossing her backpack to the floor. She didn’t even bother with greetings. "Don’t go."

Kent blinked. "What—"

"—To the gym," she cut in. Her eyes burned with clinical precision. "It’s a trap. Anonymous number? Midnight meeting? That’s the oldest ambush setup in every crime show ever. You’d be walking in blind."

Jake threw his hands up. "See? Mia gets it."

Samir’s voice crackled over a speakerphone on Mia’s desk. He hadn’t come in person—probably calculating—but he’d joined anyway. "Statistical models support her. Probability favors Derek exploiting this. Still..." His tone sharpened. "Still, it could be real. Remember—he’s losing grip. That creates dissent. And dissent seeks leaders."

Kent sank back in his chair, the conflicting voices bouncing in his skull. His heart hammered harder with every argument.

The System nudged again, its text glowing sharper than before:

[Critical Decision Pending.]

Decline: Avoid risk. (Derek maintains initiative.)

Accept: Face possible ambush. (Potential for allies, or trap.)

Jake crouched beside him. "Kent. Please. I don’t want to watch you get jumped in some moldy gym. We’ll fight Derek another way."

Mia folded her arms. "Walking into unknown variables isn’t bravery. It’s stupidity."

Samir’s voice lowered. "Sometimes, stupidity changes games. Gilbert, if you’re going to be the symbol people whisper about, symbols can’t hide. They confront."

Kent’s hands clenched. His whole life had been about hiding—shrinking, surviving in the margins. But the cafeteria, the lot, even Emily’s words... they’d shoved him into the spotlight. Whether he liked it or not, the school was watching.

His phone buzzed again. Another message.

[Midnight. The old gym. Don’t be late.]

Kent stood. His ribs screamed in protest, but his voice came out steady. "I’m going."

Jake’s jaw dropped. "You’re insane."

Mia’s glare could’ve cut steel. "Then I’m going too."

Kent shook his head. "No. If it’s a trap, I don’t want anyone else caught in it."

Jake grabbed his arm. "Forget that. You think I’m letting you walk in alone? Not a chance."

Samir’s voice was crisp, decisive. "Then we prepare. Signals. Exits. Contingencies. If it’s a trap, you escape. If it’s real..." He paused. "...then maybe you stop being a piece on the board, and start being a player."

The System chimed:

[Quest Accepted: Into the Unknown]

[Time Remaining: 02:14:32 until Midnight.]

Kent exhaled, forcing down the fear tightening his chest. The old gym waited, and with it, an answer—ally or enemy.

And for once, he wasn’t going to run.

******

The old gym hadn’t hosted a game in years.

By midnight, its windows were nothing but black squares, glass fractured in spiderwebs, some panes missing entirely. The chain-link fence sagged where students had bent it for shortcuts, and the parking lot was a graveyard of weeds and broken asphalt. The building loomed in the dark like a fossil, half-buried but still dangerous.

Kent pulled his hoodie tighter around his ribs, every step sending a dull ache up his side. Jake walked at his shoulder, flashlight beam cutting through the night, too jittery to stay silent.

"Okay, real talk," Jake whispered. "This is how horror movies start. Two idiots walk into an abandoned building at midnight, and boom, ghost clowns. Or Derek and his gorilla squad with crowbars."

"Helpful," Kent muttered, though the edge in his voice was more nerves than annoyance. His stomach was knotted, his palms clammy. The closer they got, the heavier the night felt, like the air itself knew something was wrong.

From Kent’s pocket, his phone buzzed. Another message.

[Inside. Alone.]

Jake swore under his breath. "Nope. Nope. No way. They want you alone? That’s rule number one of ’definitely a setup.’"

Kent swallowed hard, staring at the glowing text. His pulse hammered in his ears. "If I don’t go in, I’ll never know. If it’s real..." He let the words hang, unfinished.

"Or if it’s a trap, you’ll be chum," Jake shot back.

Before Kent could respond, another voice cut in from the shadows.

"Then he won’t be alone."

Mia stepped into the faint moonlight, arms crossed, her face set like stone. She wore a black jacket, hood up, and moved with the kind of quiet confidence that made Kent wonder how long she’d been tailing them.

Jake threw his hands up. "Seriously? Do none of you value your lives? Am I the only one here with survival instincts?"

"Survival isn’t just hiding," Mia said flatly. "It’s knowing when to take calculated risks." She leveled her gaze at Kent. "This could be real. And if it is, going in without backup is suicide."

Kent’s phone buzzed again.

[Alone. Or don’t come at all.]

Jake looked between them, panicked. "See? See?! That’s Derek’s guys for sure. He’s gonna shut the lights off and—bam—steel-toed boots to your ribs."

Kent’s stomach turned. His instincts screamed to walk away. But the System pulsed sharp in his vision, forcing clarity into the chaos.

[Choice Trigger: Enter or Withdraw]

Withdraw: End event. Derek maintains initiative.

Enter Alone: High risk, high reward.

Enter With Allies (Defiance): Reject terms. Risk escalation, possible discovery of true intent.

Kent clenched his fists. He was sick of being shoved around by other people’s terms—Derek’s, the System’s, anonymous threats. His ribs hurt, his reputation was a storm waiting to collapse, and yet... he couldn’t keep ducking.

He lifted his chin. "If they want me alone, that’s too bad. I’m not walking in without backup."

Jake blinked. "Wait, really?"

Mia smirked, the faintest edge of approval in her eyes. "Good. For once, you’re learning."

The System chimed:

[Alternative Path Selected: Defiance.]

[Difficulty Increase: Moderate.]

[Potential Reward: Influence Shift.]

Kent pushed open the rusted gym doors. They shrieked on their hinges, echoing into the cavernous dark beyond. The smell hit him first—dust, mildew, the faint tang of rust. Their flashlight beams carved through shadows that pooled like oil across the warped wooden floor.

The bleachers were skeletal, half-collapsed, graffiti sprawled across their backs. Broken basketball hoops hung like gallows from the ceiling, chains swaying faintly with the draft.

Jake muttered, "Yup. Definitely haunted."

Mia ignored him. Her eyes scanned every corner, every possible shadow. "Too quiet."

Kent stepped forward, each creak of the warped floorboards sharp in the silence. His pulse thundered in his ribs, every instinct screaming to turn back. But he forced his legs to move.

Then, a voice rang out. Smooth. Confident.

"Well, well. You really showed up."

From the far side of the gym, figures stepped out of the shadows.

Three of them.

Not Derek. 𝚏𝐫𝚎𝗲𝕨𝐞𝐛𝕟𝚘𝐯𝚎𝗹.𝕔𝐨𝗺

Older—college-aged, maybe. Their clothes sharp, almost too sharp, like they’d dressed to intimidate. The leader, tall and lean, had a grin that didn’t touch his eyes.

"You’re braver than I thought, Gilbert."

Kent froze. His throat tightened. "Who are you?"

The grin widened. "Friends. Or enemies. Depends on your answer."

The System’s text burned across his vision:

[New Faction Encountered: The Outliers.]

[Unknown Reputation Standing.]

Kent’s heart stuttered. Not Derek. Not a prank. Something else.

And suddenly, the trap didn’t feel smaller—it felt bigger.

The leader of the trio moved closer, his steps echoing faintly on the cracked gym floor. His presence was unsettling—not brute force like Derek, but sharp edges, the kind that cut without warning.

Jake muttered behind Kent, "These dudes look like they mug people for practice."

"Quiet," Mia hissed, but her hand shifted subtly into her jacket pocket. Kent didn’t have to guess what she was holding.

The man stopped a few feet away, his grin unwavering. "Name’s Rafe. These are my guys—Cole and Vance." He gestured lazily at the two shadows flanking him. One broad-shouldered, silent, arms folded. The other wiry, restless, fingers twitching like he couldn’t stand still.

Rafe tilted his head, studying Kent like a lab specimen. "You’ve been making noise, Gilbert. Big noise. Standing up to Derek in front of the whole school? Bold. Reckless. Impressive."

Kent forced himself not to look away. His ribs ached with every breath, but he stood firm. "And what? You came to... congratulate me?"

Rafe chuckled. "Not exactly. We came to offer perspective. You think Derek’s the big bad wolf of Ridgeway? Cute. Truth is, he’s a pawn. A loud, angry pawn. Guys like him—brute force, shallow control—they always burn out."

He stepped closer, lowering his voice just enough to draw Kent in. "The real game? Influence. Networks. Factions. Derek rules by fear, but fear crumbles the moment someone laughs at it. Which..." Rafe’s grin sharpened, "you’ve already proven."

Mia’s eyes narrowed. "You’ve been watching."

"Of course," Rafe said smoothly. "Everyone’s watching now. Gilbert’s the spark, and sparks can do two things—burn out fast, or ignite something bigger." His gaze locked on Kent. "We’re here to help you ignite."

Kent’s stomach twisted. "Help me... how?"

Rafe spread his hands, like the answer was obvious. "We’ve got resources Derek doesn’t. Reach, money, connections outside Ridgeway. You team with us, and Derek stops being a problem. We’ll tear him down piece by piece until there’s nothing left of his little kingdom."

Jake whispered, "Okay, sounds great. Where do I sign?"

Mia shot him a glare that could have melted steel. "What’s the catch?"

Rafe’s grin widened like he’d been waiting for that. "Simple. Loyalty. You roll with us, you back us when the time comes, and in return, we make sure you rise. Influence, protection, reputation—you’ll have it all. But it means you stop playing solo." His voice dipped, colder. "No more half-measures. No more hiding behind accidents and lucky comebacks. You pick a side."

The air thickened with the weight of his words.

Kent’s throat felt dry. The System pulsed again, crisp text lighting up his vision:

[Quest Trigger: The Outliers’ Hand]

Objective: Decide response to the faction’s offer.

Options:

Accept: Join The Outliers. Gain faction protection. Lose independence.

Decline: Maintain freedom. Risk retaliation from The Outliers.

Stall: Buy time. Risk suspicion, but retain choice later.

Kent’s mind spun. Every instinct screamed this was dangerous—trading one predator for another. But Rafe’s words weren’t wrong. Derek was already plotting retaliation, and Kent was running out of time.

Jake leaned close, whispering, "Dude... allies. You need allies. Even shady ones."

Mia, sharp as ever, muttered from his other side, "Allies who demand loyalty usually mean shackles. Don’t sell yourself to someone you don’t even know."

Kent stood in the middle, heart pounding, three sets of eyes burning into him—Jake’s anxious, Mia’s guarded, Rafe’s hungry.

He realized the silence had stretched too long. Rafe’s grin flickered, thinning at the edges.

"Tick-tock, Gilbert," Rafe said softly. "We don’t make offers twice."

The System’s text pulsed again:

[Warning: Failure to respond will result in reputation loss with The Outliers.]

Choose. Now.

Kent drew in a shaky breath. His ribs screamed. His head spun.

But he knew—whatever he said here would echo far beyond the walls of this ruined gym.

The silence stretched taut, like the gym itself was holding its breath. Dust drifted lazily through a slice of moonlight cutting across the cracked floor. Kent could hear his own pulse pounding in his ears, a relentless drumbeat against the tension.

Rafe tilted his head, his grin no longer playful. "I’ll say it again, Gilbert. We don’t offer twice. You’re either with us, or you’re nothing."

Jake fidgeted beside him, whispering, "Bro, just say yes. At least buy time before Derek crushes you."

Mia’s hand pressed lightly against Kent’s arm, her voice razor-sharp but hushed. "Don’t. You can’t tie yourself to a gang you don’t control. That’s trading Derek for another leash."

The System chimed in Kent’s vision, merciless as always:

[Decision Point: The Outliers’ Offer]

Accept: Gain faction benefits. Lose autonomy.

Decline: Risk Outliers’ hostility. Retain freedom.

Stall: Delay outcome. Danger of suspicion.

Kent inhaled, ribs screaming with every breath. His thoughts raced. Accepting meant protection, sure—but also shackles. Declining would make enemies of people who clearly weren’t afraid of Derek. And stalling? That might only buy a sliver of time before the knife came anyway.

He straightened slowly, forcing his voice steady. "You want loyalty?" He met Rafe’s sharp gaze head-on. "Loyalty’s earned, not bought. If you really think I’m worth backing, prove it first."

The Outliers shifted, surprise flickering across their faces. Rafe’s grin froze for the first time. Behind him, Cole’s broad shoulders stiffened, while Vance actually snorted in amusement.

"Bold," Vance muttered. "Cocky little bastard."

Mia’s grip on Kent’s arm loosened, approval flashing in her eyes. Jake, on the other hand, looked like he was about to faint.

Rafe’s silence stretched long enough to make the air thick. Finally, he laughed. Low at first, then building, echoing off the gym walls.

"You’ve got teeth after all," he said, amusement sliding back into his voice. "Most kids would’ve bent the knee already. You..." His eyes glinted, sharp and assessing. "You want proof? Fine. We’ll give you proof."

He snapped his fingers. Cole stepped forward, producing a folded piece of paper from his jacket and tossing it onto the floor at Kent’s feet.

Kent hesitated before crouching to pick it up. His ribs ached as he unfolded the page.

It wasn’t a note. It was a photo.

Derek. Laughing, his arm slung around one of his crew in front of the Riverside Lot. But behind him, in the corner of the frame, a car window was cracked—just enough to reveal a flash of a weapon inside.

Kent’s stomach turned. A gun.

Rafe’s voice cut through the silence. "Derek’s not playing schoolyard bully anymore. He’s got people. Dangerous people. If you think bruises are the worst you’ll face, you’re dead wrong."

Jake’s breath hitched. "Holy—are you saying Derek—"

"I’m saying," Rafe interrupted smoothly, "you’ve got a choice. Walk blind and get buried, or walk with people who know how the game really works. We’ll handle Derek’s little... extracurriculars. But you?" His eyes narrowed. "You need to decide if you want to stay prey, or start hunting."

The System pulsed again, bright and insistent:

[New Quest Branch Unlocked: Predator or Prey]

Accept Outliers’ support → unlock faction path.

Reject → trigger Rivalry escalation.

Remain neutral → increased danger, hidden opportunities.

Kent folded the photo slowly, his jaw tight. Every eye in the gym was on him. He could feel Mia’s approval, Jake’s fear, and Rafe’s sharp hunger pressing against him all at once.

He pocketed the photo. "Then I’ll think about it."

Rafe studied him for a long, heavy beat. Then he smiled—not wide this time, but thin, sharp, almost predatory. "Fair enough. But don’t think too long, Gilbert. Choices expire."

He snapped his fingers again. The Outliers melted into the shadows as suddenly as they’d appeared, leaving only dust motes swirling in the empty gym.

The silence that followed was deafening.

Jake finally exhaled, collapsing onto a broken bench. "Dude... DUDE. What the hell was that? They’re like the—like the villain DLC expansion pack!"

Mia didn’t smile. Her gaze was sharp, calculating. "They gave you a warning. Derek’s more dangerous than we thought. And now you’ve got another faction circling you, waiting to see if you’ll bite."

Kent’s ribs throbbed as he sank against the wall, the folded photo burning hot in his pocket.

The System’s last words for the night pulsed across his vision, crisp and cold:

[Quest Update: Predator or Prey]

Timer: 72 hours until Outliers demand answer.

Warning: Rivals escalating in parallel. Multiple threats converging.

Kent closed his eyes, exhaustion washing over him. He wasn’t sure which terrified him more—Derek’s fury, or the smile Rafe had left behind.

The old gym’s doors groaned as they swung shut behind Kent, the sound reverberating like the final toll of a bell. Outside, the night pressed heavy, damp air clinging to his skin. The streets were deserted—too late for stragglers, too early for morning joggers. Just him, Mia, and Jake, their footsteps echoing against cracked pavement.

Jake broke the silence first. "So... are we just not going to talk about the fact we almost got recruited by a gang? Because, uh, my brain is melting."

"Not ’we,’" Mia corrected. Her arms were folded tight across her chest, her jaw clenched. "Him. They want Kent."

"Yeah, well, Kent almost told them to shove it," Jake muttered. "Which I respect, by the way. Bold. Suicidal, but bold."

Kent walked slower than usual, every step tugging at his bruised ribs, every thought snagging on the folded photo in his pocket. He hadn’t shown them yet. Couldn’t. Not until he processed it himself.

But Mia noticed anyway. "They gave you something," she said flatly.

Kent glanced at her, startled. "How—"

"You’ve had your hand in your pocket since they left," she said. Her eyes narrowed. "Show me."

Reluctantly, he pulled out the photo, passing it to her. Moonlight hit the glossy surface as she studied it. Her lips pressed into a thin line.

Jake leaned over her shoulder, then staggered back. "Holy crap. That’s a—"

"Shut up," Mia snapped. She folded the photo and shoved it back into Kent’s hands, her voice low and urgent. "Don’t show this to anyone else. Not Samir. Not even Jake."

"Hey!" Jake protested.

Mia ignored him, her gaze drilling into Kent’s. "If Derek really has access to this, then the game changed. This isn’t about popularity contests anymore. This is—" She broke off, glancing at the empty street. "This is dangerous in ways none of us signed up for."

The System pulsed in Kent’s vision, as if confirming her words:

[Warning: Threat Level Escalation]

New Variable Identified: Potential Lethal Force.

Kent’s throat went dry. He shoved the photo deep into his pocket, like burying it might erase what he’d seen.

Jake scratched the back of his neck nervously. "So what, we just... wait for Derek to go full mafia boss? Or do we call the cops? Because I don’t know about you guys, but I like being alive."

Mia’s reply was sharp. "Cops won’t do anything without proof that holds up. And if Derek’s smart, nothing will trace back to him." She shot Kent a look. "You know what that means."

Kent swallowed. "We need to be smarter."

"Exactly," she said.

The rest of the walk was tense, every shadow feeling heavier, every passing car a possible threat. When they finally reached Kent’s street, Jake let out a shaky laugh. "I don’t know about you guys, but I’m never sleeping again."

Mia gave him a withering glare. "Grow up, Jake."

But Kent barely heard them. His mind was a whirl of Derek’s glare in the cafeteria, Rafe’s predatory smile, the cold gleam of the gun in the photo.

He stopped at his front gate, looking back at them. "Thanks for coming tonight. I... I couldn’t have handled it alone."

Jake clapped him gently on the shoulder. "That’s what bros are for, man."

Mia’s gaze softened, just for a second. "Rest. Tomorrow, we figure out next moves."

They left him there, their silhouettes fading into the dark.

Kent slipped inside quietly, the house dark except for the faint glow of the kitchen clock. His mom was asleep. He crept upstairs, every step weighed down by exhaustion.

In his room, he shut the door and pulled the photo back out, staring at it under the lamplight. The image seemed even heavier now, like it carried its own gravity.

The System pulsed one last time:

[Quest Log Updated]

Predator or Prey – Countdown: 71 Hours

Sub-Objective: Withhold photo or expose it? Consequence branches diverge.

Kent dropped onto his bed, the photo clutched tight in his hand. His bruises throbbed. His thoughts spun.

And for the first time since the fight in the lot, he realized: this wasn’t just about Derek anymore.

It was about survival.