Tim Drake oneshots

(3) New Persona

Tim sat perched on the edge of a rooftop in Gotham, scanning the dimly lit streets below. After his flirtatious escapades at the Wayne gala and the Watchtower, the idea had been bouncing around in his head all week. Could he really pull this off with Gotham’s Rogues? The people most likely to throw a punch (or a grenade) his way? The thought had him grinning, despite knowing it was a bad idea. Maybe that was what made it so tempting.

It wasn’t long before his comms buzzed in his ear.

“Tim,” Bruce’s deep voice cut through the static. “Why are you out tonight? You’re supposed to be on research duty.”

Tim sighed theatrically. “Come on, Bruce. I can’t be cooped up with paperwork all night. I needed some fresh air.”

“Fresh air?” Bruce sounded suspicious. “You’re not up to something, are you?”

“Me?” Tim asked innocently. “Never.”

There was silence on the other end before Bruce responded in a low tone. “Whatever it is, don’t. Gotham’s quiet tonight. Don’t start anything.”

Tim smiled. “Got it, boss.”

The second Bruce cut the comm, Tim sprang into action. He had no specific target in mind, but the city never disappointed when it came to villains crawling out of the woodwork.

His first stop: The Iceberg Lounge.

---

Tim slipped into the Iceberg Lounge, dressed down from his usual Robin gear, blending into the crowd of Gotham’s elite and the occasional lowlife who thought they belonged there. He moved with ease through the casino floor, looking for his prey. And there he was, behind the bar’s glass case, adjusting his tie—Oswald Cobblepot, the Penguin himself.

Penguin rarely did his own dirty work these days, but his ice-cold demeanor still held power. Tim slipped up to the bar, leaning casually against it, making sure to catch Cobblepot’s eye.

“Mr. Cobblepot,” Tim greeted, his voice smooth. “Nice to see you looking so dapper tonight.”

Penguin glanced up, startled at first, but then his eyes narrowed. “Who the hell are you? Another brat trying to get my attention?”

Tim chuckled, meeting his eyes with a smirk. “Just admiring the way you run the place. Iceberg Lounge is a class act. And, honestly, that suit? Sharp.”

Penguin blinked, clearly thrown off. “You think flattery’s gonna get you anywhere with me, kid?”

Tim leaned in a little, his voice lowering conspiratorially. “Oh, I’m not looking for anything… yet. Just paying my respects to a man who’s been running Gotham’s underground scene for longer than most of us have been alive. That’s worth admiring, don’t you think?”

Penguin squinted at him, trying to gauge the sincerity behind the words. His sharp, beady eyes narrowed, but Tim could see the subtle shift in his posture. He was intrigued. The flattery was working, though he’d never admit it.

“You’ve got some nerve, walking in here talking like that,” Penguin grumbled. “But I suppose it’s not the worst compliment I’ve heard.”

Tim grinned. “You’re welcome.”

Before Cobblepot could dig any deeper, Tim caught sight of the lounge’s second-floor balcony. His next target had just arrived: Harley Quinn, dressed in her typical red-and-black ensemble, leaning over the balcony railing, surveying the room with a wicked grin. This was going to be interesting.

---

Tim slipped past a few goons and made his way upstairs, approaching Harley with a smile as she spotted him out of the corner of her eye. She tilted her head, her grin widening as she recognized him.

“Well, if it ain’t one of Batsy’s brats!” Harley exclaimed, her voice high and playful. “Whatcha doin’ here, sweet cheeks?”

Tim chuckled, leaning against the railing beside her. “Just enjoying the view, Harley. You always know how to make an entrance.”

She looked him up and down, clearly trying to figure out what game he was playing. “Flattery, huh? You hittin’ on me, kid? Ain’t you a little young?”

Tim smirked. “Maybe, but age is just a number, right? Besides, I always did like a woman with a wild side.”

Harley’s eyes widened for a split second before she burst into a fit of laughter. “Oh man, you’ve got guts! And here I thought you were the boring one.”

Tim winked. “I’m full of surprises.”

Harley wiped a tear from her eye, still laughing. “I gotta say, you’ve got some spunk, but you’re messin’ with fire, you know that?”

“Maybe,” Tim said, shrugging nonchalantly. “But a little fire never hurt anyone.”

Harley gave him a long look before poking him in the chest. “Careful, kid. You don’t wanna play with me unless you know what you’re doin’.”

“Oh, I know,” Tim replied smoothly, standing up straight. “But who said I wasn’t?”

Harley looked genuinely surprised for a second, before she grinned wide again. “You’re funny! I’ll give ya that.”

Before Tim could continue his playful back-and-forth, he caught sight of a hulking figure entering the lounge below. Killer Croc. The giant lizard-man always looked out of place in such a classy setting, but there he was, towering over everyone, snarling at one of the waiters.

Tim turned to Harley. “I think my next target’s here.”

Harley followed his gaze, then gave him a pat on the back. “Good luck, toots! Croc ain’t exactly the flirty type.”

Tim grinned. “I’ll take my chances.”

---

Tim descended the staircase and made a beeline for Croc, who was busy intimidating the staff. He had to think quickly—Croc wasn’t known for his patience. But Tim was determined to see how far he could push this.

“Hey, Croc!” Tim called out, approaching with a confident swagger.

Croc growled, turning to face him. “What do you want, kid?”

Tim flashed his signature smirk. “Just wondering how you keep that skin looking so… rugged. Got any tips?”

Croc blinked, momentarily stunned by the question. “What?”

“I mean, I know a lot of guys would kill for a look that intimidating,” Tim continued, undeterred. “You really pull it off.”

For a moment, Croc seemed caught between confusion and anger. Then, unexpectedly, he snorted. “You’re weird, kid.”

Tim shrugged. “Maybe. But it works, doesn’t it?”

Croc gave him a long, hard look before shaking his head. “You’ve got a death wish, you know that?”

Tim smiled, taking a step back. “I hear that a lot.”

---

As Tim left the Iceberg Lounge, his mind buzzed with adrenaline. He couldn’t help but laugh at how each encounter had gone. Flirting with the Rogues had been a risky move, but surprisingly, no one had tried to kill him. Yet.

His comms crackled to life in his ear again. “Tim,” Bruce’s voice was gruff. “Report.”

Tim smirked. “Just keeping things interesting, Bruce. Nothing to worry about.”

Bruce’s long pause spoke volumes, and Tim could practically feel the disapproval radiating through the comms. “I’ll be back soon,” Tim added, cutting the line before Bruce could lecture him.

As he leaped off the rooftop into the night, he couldn’t help but wonder what his next flirtatious adventure might be.

Maybe Gotham wasn’t the only city with interesting personalities.