Tim Drake oneshots

(4) New Persona

Tim had just started his solo patrol, bounding across the rooftops of Gotham, when his comm crackled to life. Oracle’s voice came through, steady as always.

“Tim, I’m seeing a lot of activity near the docks. Looks like Penguin’s crew is moving something big. You might want to check it out.”

Tim smirked as he adjusted his domino mask. “The docks, huh? I wonder if Oswald’s still thinking about my compliment from the other night.”

Barbara’s voice paused for a beat. “...You’re still on that?”

“Hey, I’m just saying, it’s fun. Don’t you think Gotham’s Rogues deserve a little positive attention now and then?”

“Just be careful,” Barbara sighed. “If you get in over your head, I’m not bailing you out.”

Tim chuckled as he clicked off the comm. “Got it. Just a little friendly banter with Gotham’s villains—what could possibly go wrong?”

---

The docks were quiet as Tim arrived, moving like a shadow between stacks of shipping containers. It wasn’t long before he spotted Penguin’s goons unloading crates from an unmarked van. And there, standing a few feet away, barking orders with his typical gruff voice, was Oswald Cobblepot.

Tim dropped down onto the shipping container directly in front of Penguin, landing gracefully with a flourish. “Well, well. If it isn’t Gotham’s finest businessman, hard at work. Oswald, it’s a pleasure, as always.”

Penguin’s monocle caught the light as he looked up at Tim, scowling. “Red Robin. You again? Didn’t I tell you to keep your snarky comments to yourself last time?”

Tim jumped down from the container, stepping closer. “I wasn’t sure if you meant it. After all, you seemed to like it. You know, you really do run a tight operation here. It’s… impressive.”

Penguin grumbled, clearly irritated, but he was trying to maintain his composure. “You got guts, kid, but flattery ain’t gonna stop me from running my business. So unless you plan on doing something about it—”

Tim leaned in, lowering his voice as if sharing a secret. “Or maybe I just came by to admire the man behind the operation. A little praise never hurt anyone, right?”

Penguin blinked, momentarily speechless. The goons nearby exchanged confused glances, unsure of what they were witnessing.

“Are you flirting with me, Red Robin?” Penguin asked incredulously.

Tim grinned. “Maybe. Is it working?”

Before Penguin could sputter out a response, a figure emerged from the shadows nearby. The slinking, graceful form of Poison Ivy stepped into the light, her green eyes narrowing as she took in the scene.

“Well, if it isn’t the little bird,” Ivy purred, her voice silky smooth. “What’s this I hear about you buttering up Gotham’s most eligible bachelor?”

Tim straightened up, turning to face Ivy with a confident smile. “Ivy. You’re looking radiant tonight. The plants must be doing wonders for your complexion.”

Ivy’s lips curled into a smirk as she stalked closer, her movements slow and deliberate. “I see you’re just as charming as ever, little Robin. Though I’d be careful if I were you. Not all of Gotham’s Rogues are as… forgiving as I am.”

Tim didn’t back down, meeting her gaze with the same playful smirk. “Forgiving? Ivy, I’d say you’re practically a saint compared to the rest of the crowd. I mean, all you want is to make the world a greener place. How could anyone fault you for that?”

Ivy’s eyes flashed with amusement as she stopped just in front of him, leaning in slightly. “Careful, Timmy. Flattery can be dangerous if you don’t know how to use it. But I must say, you’re doing well so far.”

Before Tim could reply, a familiar voice echoed through the docks.

“Well, well, what have we here? Red Robin, charming the villains of Gotham again?”

Harley Quinn bounced into view, her baseball bat slung over her shoulder as she approached with a wide grin. “You really know how to make a gal feel special, don’t ya? First me, now Ivy, and even old Penguin here. What’s next, you gonna write us all love letters?”

Tim laughed, turning to Harley. “You know me, Harley. I’m just trying to spread a little love in Gotham. Someone has to.”

Harley laughed along with him, clearly enjoying the banter. “You’re a riot, kid! I always said you were the fun one.”

As the three villains circled him—Penguin still looking perplexed, Ivy intrigued, and Harley outright entertained—Tim realized they were now fully in his game. The goons around them had paused their work, watching the bizarre interaction unfold.

“So what’s the deal, huh?” Harley asked, leaning on her bat. “You sweet-talkin’ all of us now? What’s next, you gonna ask Ivy out for a vegan dinner or somethin’?”

Tim smirked. “You know, that doesn’t sound like a bad idea. Ivy, care to grab a bite sometime? I hear there’s a new eco-friendly restaurant downtown.”

Ivy raised an eyebrow, clearly entertained by the boldness. “Oh, Timmy. You wouldn’t be able to handle it.”

Harley cackled, hopping up on a crate and swinging her legs. “Aw, come on! Let the kid try! I bet he’s got a few surprises.”

Penguin, however, was losing his patience. “Enough of this nonsense! Red Robin, if you think a few sweet words are gonna stop me from getting my shipment out, you’ve got another thing coming.”

Tim turned back to Penguin, his grin widening. “Oh, Oswald. I’d never dream of stopping you. I’m just here for the company.”

Penguin’s face turned red as he puffed out his chest. “You—”

But before he could finish, a shadow moved across the dock, and the unmistakable figure of Red Hood dropped down from above, landing beside Tim.

“Am I interrupting something?” Jason asked, his voice dripping with sarcasm as he surveyed the scene.

Tim smirked. “Just a friendly conversation with some of Gotham’s finest.”

Jason crossed his arms, glancing at the villains. “You know, most people would just punch them and be done with it.”

Tim shrugged. “Where’s the fun in that?”

Penguin, clearly done with the situation, barked at his goons to finish loading the crates. “Enough! We’re leaving. And you, Red Robin—stay out of my way.”

Tim waved casually as Penguin stormed off, his crew following close behind. Ivy lingered for a moment longer, her green eyes sparkling with amusement.

“See you around, Timmy,” she purred before slipping into the shadows.

Harley hopped down from the crate, giving Tim a wink. “You’re a real charmer, bird boy. Don’t go changin’!” And with that, she followed Ivy into the night.

Once they were gone, Jason turned to Tim with a raised eyebrow. “Seriously? Flirting with Ivy and Harley? You’ve got a death wish.”

Tim chuckled. “Hey, it worked, didn’t it? No one got hurt.”

Jason sighed, shaking his head. “You’re unbelievable. Bruce is gonna kill you when he hears about this.”

Tim grinned, already imagining Bruce’s reaction. “Totally worth it.”