Picking Up Girls With My Pickup System-Chapter 8: An Unexpected Ally.

Kent hadn’t slept much. Every time he closed his eyes, he saw Derek’s fist cocked back, ready to end his life, only to be saved by Coach barging in.

When he walked into school the next morning, the hallway buzzed with more noise than usual. The second he stepped past the doors, heads turned.

"There he is," someone muttered.

"That’s the guy who mouthed off to Derek."

"Bro’s insane... or suicidal."

Kent gripped the straps of his backpack tighter, trying to keep his eyes forward. His heart raced. Oh no. Oh no. They all know.

A cluster of sophomores near the lockers glanced at him, then broke into laughter. Kent’s ears burned.

At the drinking fountain, a pair of cheerleaders whispered behind their hands, their eyes flicking toward him. One of them smirked.

Kent’s stomach twisted. They’re all laughing at me. They think I’m a joke. Why did I listen to that stupid System?

The voice in his head chimed in cheerfully.

[Update: Host’s reputation has increased. Current Reputation: 12/100.]

[Note: Infamy still counts as reputation.]

Kent muttered under his breath, "That’s not helping."

At his locker, Todd leaned against the metal door like he’d been waiting. "Well, well, if it isn’t our little stand-up comedian."

Kent froze. "Todd."

Todd grinned, his voice carrying just enough for others nearby to hear. "Word’s going around that you’ve got a death wish. You’re not gonna make it to prom, Gilbert."

Laughter rippled from a few eavesdroppers. Kent’s throat went dry, but he forced himself not to shrink back. If he did, it would prove Derek right—that he was just a punching bag.

The System’s text flickered faintly in his vision.

[Micro-Quest Generated: Do not flinch when threatened. Reward: +1 Confidence.]

Kent swallowed hard. His knees wanted to buckle, but he tightened his jaw and met Todd’s gaze.

"Prom’s months away," Kent said, voice steady despite the quake in his chest. "Guess we’ll see if your boss can wait that long."

The kids around them let out a collective "oooh," like the sound of a crowd at a rap battle. Todd’s smirk faltered for just a second.

The System chimed.

[Micro-Quest Complete. +1 Confidence.]

Kent’s chest swelled—not much, but enough to keep him from running away.

Still, as Todd stalked off, muttering curses under his breath, Kent knew this was only going to make Derek angrier.

And judging by the way the whispers chased him through the hallways, everyone else knew it too.

Kent kept his head down most of the morning, avoiding eye contact. Every time a locker slammed or someone laughed behind him, his pulse spiked.

By lunch, he’d decided to eat outside under the bleachers, away from the cafeteria stares. He balanced a half-crushed sandwich in his lap when a shadow crossed over him.

"Skipping the crowd, huh?"

Kent looked up—and nearly dropped his sandwich. "Lena?"

She stood there in her café apron, tied loosely over a simple white blouse and jeans. Her hair was pinned back with a pen, as though she’d dashed straight from work. She looked wildly out of place among the teenage cliques roaming the quad.

"You—what are you doing here?" Kent stammered.

Lena smiled, brushing a strand of hair behind her ear. "Relax. I’m not stalking you." Her eyes sparkled mischievously. "I’m helping my cousin with a photography project. They’re a senior here. I figured I’d drop by and, oh, look who I found."

A few students at nearby tables had already noticed her. Whispers spread like wildfire.

"Who’s that with Gilbert?"

"No way—he knows her?"

"She’s hot."

Kent’s stomach lurched. He was being watched again, except this time it wasn’t laughter—it was envy.

Lena sat down right next to him, close enough for her perfume to tickle his nose. She glanced at his squished sandwich and frowned. "That’s your lunch? Tragic."

Kent wanted to melt into the ground. "It’s... uh... protein?"

She laughed—a warm, genuine sound—and leaned her elbow on the bench. "You’re funny when you’re not trying."

The whispers around them swelled. Kent could feel every eye drilling into the back of his head. His palms grew clammy. Why here? Why now?

And then, across the quad, he saw him.

Derek.

Leaning against a tree with his crew, watching. His expression was unreadable, but the tension in his jaw made Kent’s stomach knot.

The System’s cheerful ding echoed in his head.

[Optional Mission Unlocked: Flirt with Lena in public. Reward: Random Skill Upgrade. Failure: -2 Confidence.]

Kent’s eyes widened. Flirt? In public? With everyone watching?

The System helpfully added:

[Warning: Failure may result in social humiliation.]

Kent’s throat went dry as Lena arched a brow, waiting for him to say something.

Kent’s pulse hammered against his ribs. The mission text glowed in the corner of his vision like neon graffiti on a brick wall.

[Optional Mission: Flirt with Lena in Public.]

[Reward: Random Skill Upgrade.]

[Failure Penalty: -2 Confidence.]

He nearly choked on his own spit. Flirt? Here? In front of Derek? In front of the entire cafeteria’s worth of gossip vultures?

Lena tilted her head. "You look like you just saw a ghost. Everything okay?"

Kent’s brain scrambled for an escape hatch. Maybe he could laugh it off, maybe he could—

The System buzzed insistently.

[Timer: 45 seconds remaining to accept mission.]

"Oh, come on," Kent whispered under his breath.

"What’s that?" Lena asked.

"Uh—uh, nothing! Just... allergies." His voice cracked. Smooth. Real smooth.

[30 seconds.]

Kent’s palms slicked with sweat. He glanced around. Everyone was watching—some curious, some snickering, some outright glaring. Derek’s jaw flexed as though he could already hear the punchline.

If I screw this up, I’m done.

But then—just faintly—another thought crept in. What if I don’t screw it up? What if... I actually pull it off?

[10 seconds.]

Kent squeezed his fists until his knuckles whitened.

"Fine," he muttered under his breath.

[Mission Accepted.]

The System chirped happily.

[Flirtation subroutines online. Suggestion Module unlocked.]

Kent blinked—and then, like subtitles in his vision, a line of text appeared:

[Suggested line: "You make this whole place look boring by comparison."]

Kent’s heart nearly stopped. I can’t say that! That’s... that’s actually smooth!

Lena blinked at him, waiting.

The whispers around him grew louder. Derek’s eyes narrowed.

Kent swallowed hard. His tongue felt like lead. He opened his mouth—

Kent’s voice cracked as he forced the words out. "Y-you, uh... make this whole place look boring by comparison."

For half a second, silence blanketed the quad.

Kent wanted to vanish. His face flamed red. He braced for laughter, for Lena to roll her eyes, for Derek to storm over and smash him against the table.

Instead—

Lena blinked. Then she smiled. Slowly.

"Oh?" She leaned in, her elbow brushing his arm as she propped her chin on her hand. Her eyes sparkled like she’d just been handed front-row tickets to the best comedy show in town. "That’s a pretty bold thing to say, Kent Gilbert."

A few students gasped.

"No way..."

"Did he just—"

"She didn’t laugh at him?"

Kent’s ears buzzed. He had no idea if he’d just won or lost, but Lena’s grin didn’t look cruel. It looked... entertained. 𝙛𝓻𝒆𝒆𝒘𝙚𝓫𝙣𝙤𝒗𝙚𝓵.𝙘𝙤𝙢

The System flashed again.

[+1 Charm for Successful Delivery.]

[New Line Unlocked: Follow-up Banter.]

[Suggestion: ’What can I say? I’m a risk-taker.’]

Kent gulped. His body moved before his brain caught up. "What can I say? I’m a risk-taker."

Lena chuckled softly, tilting her head. "A risk-taker, huh? Dangerous reputation for a high school kid."

Whispers around them grew louder. Some kids actually looked impressed. Others traded disbelieving looks like they’d stepped into an alternate dimension.

Across the quad, Derek’s expression darkened. His knuckles whitened against the tree bark.

Kent caught it out of the corner of his eye. A shiver ran down his spine, but Lena’s warm laugh anchored him in place.

The System chimed:

[Mission in Progress. Keep momentum.]

Kent leaned back slightly, feigning more confidence than he felt. "Dangerous can be exciting, right?"

Lena’s lips curved into a sly smile. "Careful, Gilbert. Exciting people usually end up breaking hearts."

The crowd around them murmured like they were watching a soap opera unfold live.

Kent’s insides twisted into a knot, but he forced a smirk. "Guess you’ll have to stick around to see if I do."

For a moment, Lena just looked at him—searching his face, measuring whether he was bluffing or not. Then she laughed again, softer this time, shaking her head.

"You’re something else."

The System blared in triumph.

[Optional Mission Complete! Reward Granted: Random Skill Upgrade.]

[Congratulations, Host! New Skill Acquired: Quick Wit (Lv.1) — Your comeback lines will now strike faster and sharper.]

Kent’s vision swam with excitement. His first skill.

But the glare burning into his skin reminded him this victory came with a price.

Derek wasn’t going to forget this.

******

The bell finally shrieked, scattering the crowd like startled birds. Conversations lingered, but one by one the students drifted back inside, buzzing about the unexpected lunchtime spectacle.

Kent remained frozen on the bench, staring at his half-eaten sandwich as if it had betrayed him. His heart still thumped like a war drum.

Lena nudged him with her shoulder. "You okay there, Romeo? You look like you just ran a marathon."

Kent croaked, "I thought I was going to die."

She laughed, rich and amused. "You didn’t. In fact... you kinda killed it."

Kent blinked. "I... what?"

Lena leaned closer, her perfume tickling his senses. "You were smooth, Kent. Way smoother than I expected. Got me curious."

His brain short-circuited. Smooth? Me?

The System chimed politely.

[Skill ’Quick Wit’ Activated.]

[Effect: Faster, sharper responses. Bonus: +5% Charm in banter.]

And just like that, words bubbled up before he could think twice. "Careful, Lena. Curiosity can be dangerous."

He slapped a hand over his mouth immediately after. Oh crap. Did I just say that out loud?

Lena’s eyes widened for a moment—then she broke into a grin, teeth flashing as she laughed. "Dangerous again, huh? Guess that’s your brand now."

Kent’s face burned, but for once, not from humiliation.

"Seriously, though," Lena said, rising from the bench and dusting off her apron, "don’t let that crowd eat you alive. They’re sheep. Today? You weren’t."

She gave him a playful salute before walking off, hips swaying casually.

Kent sat there stunned, staring after her. His chest felt tight, but not from dread—something else. Something foreign.

The System hummed like a cat in his ear.

[Host’s Reputation has increased. Current Reputation: 18/100.]

But when Kent finally tore his gaze away, he spotted Derek at the far end of the quad. Still watching.

And this time, Derek wasn’t hiding the storm in his eyes.