Tim Drake oneshots

(5) New Persona

It was a quiet night in the Batcave, a rare occurrence for Gotham. Tim sat at the large computer desk, absently tapping his fingers as he stared at the glowing screen. He had just finished another patrol, one that had been suspiciously devoid of villain activity. No heists, no breakouts, nothing. Even Harley had been strangely silent over the last week, which was an anomaly in itself.

As he leaned back in his chair, Tim’s mind wandered to the last interaction he had with the Rogues, especially Harley. She had been half-joking, but her suggestion had stuck with him. "You gonna write us all love letters?" she had teased, and now, that idea seemed both ridiculous and... oddly tempting.

Why not? He had been messing with them for weeks now, flirting and throwing them off their game. This would just be the next level of the joke, a way to keep them on their toes—and have a little fun in the process.

"Alright, let's do this," Tim muttered to himself with a grin, grabbing a notepad and pen from the side of the desk. He was going to write each of Gotham's most notorious villains a love letter—Harley’s idea, but with his own twist. It’d be harmless fun… hopefully.

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Letter 1: Harley Quinn

“Dear Harley,

I must confess that, despite your chaotic nature, there’s something endlessly charming about the way you swing that bat. It’s not just your acrobatics or your infectious laugh, but the way you keep everyone guessing—me included. I’ve always been a fan of surprises, and you, Harley, are the best kind of surprise.

Let’s call it what it is—you’ve got a killer personality. How could anyone resist? So next time you’re thinking about robbing a bank or smashing some skulls, maybe leave a little time to smash my heart too. You’ve already cracked it, after all.

Yours chaotically, Robin (Tim, if you prefer.)”

Tim leaned back, admiring his handiwork. He knew Harley would get a kick out of it. It was lighthearted enough to stay on the safe side but definitely flirty enough to keep her guessing.

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Letter 2: Poison Ivy

“Dear Ivy,

You know, they say beauty is deadly, but I think you’ve mastered that art. Every time I see you, it’s hard to decide what’s more dangerous—your plants or your smile. You’ve got that ethereal, untouchable quality, but I can’t help being drawn in like a moth to a flame—or in your case, a flower.

I could talk about how you’re one of Gotham’s most formidable eco-warriors, but that’s just stating the obvious. What’s more interesting is that underneath all that dangerous charm, you care. And that, Ivy, is the most attractive thing of all.

If you ever need someone to water your plants—or, you know, just hang out—I’d be happy to be the one.

Warm regards (in the most sustainable way), Tim”

He smirked as he set the second letter aside. Ivy would probably appreciate the compliment to her cause, even if it came with a healthy dose of teasing. Besides, what was the harm in it?

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Letter 3: Selina Kyle (Catwoman)

“Selina,

I’d call you a thief, but the truth is, you’ve stolen something far more valuable than jewels—you’ve stolen my attention. There’s something about the way you move, always ten steps ahead of everyone else. It’s... mesmerizing. I’d chase you across every rooftop in Gotham, just to catch a glimpse of that sly smile when you think you’ve gotten away.

But we both know you never really run away, do you? You always come back. And for that, I’m grateful.

Next time we cross paths, maybe we could skip the heist and have a rooftop dinner instead? I’ll bring the catnip.

Yours, with no strings attached, Tim”

He chuckled softly. Selina would probably roll her eyes, but deep down, he suspected she’d appreciate the humor. She always did love toying with people, and Tim wasn’t afraid to play the game.

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Letter 4: The Riddler

“Dear Eddie,

I’ve always loved puzzles, and I have to say—you might just be the most interesting one I’ve come across. Every time I think I’ve figured you out, you throw me another riddle, another twist. It’s... frustratingly fun.

You’re sharp, you’re clever, and most of all, you keep me on my toes. What more could I ask for in a nemesis? Or maybe something more? Who knows, maybe one of these days I’ll crack the code that is Edward Nigma. But until then, I’ll keep enjoying the challenge.

Here’s a riddle for you: What’s green, charming, and impossible to forget? Answer: I think you already know.

Looking forward to our next game, Tim”

Tim smirked, imagining Riddler’s reaction to a riddle he hadn’t come up with himself. Knowing Eddie, he’d probably send back a dozen more riddles just to keep the game going.

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Letter 5: Oswald Cobblepot (The Penguin)

“Dear Oswald,

You know, most people underestimate you, but I think you’ve got a certain... refinement. Sure, you run Gotham’s underworld, but let’s not pretend you don’t have a certain elegance about it. The way you carry yourself, the suits, the cigars—classy, really.

I’d say it’s refreshing to meet a villain with style, but let’s be real—you set the standard. So, here’s to you, Oswald, for keeping things classy, even when things get messy.

If you ever want to swap tips on keeping a tux looking sharp, I’m your guy.

Stay dapper, Tim”

He laughed softly, knowing Penguin’s ego might actually enjoy a little ego-stroking, even if it came from one of his enemies.

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Letter 6: Bane

“Dear Bane,

Strength comes in many forms, and while I can’t deny you’ve got plenty of it physically, I think it’s your resilience that’s most impressive. You’ve been through a lot—more than most people can imagine—and yet, you stand tall. I respect that.

I’m not one for brute force, but I can appreciate someone who’s built themselves up the way you have. It’s admirable, really. Maybe next time we meet, instead of trying to break me, we can have a conversation? Who knows, maybe we’ve got more in common than you think.

Either way, you’ve got my attention, Bane.

Respectfully, Tim”

He placed the final letter down, smirking at the absurdity of it all. Bane probably wouldn’t take kindly to the sentiment, but it was worth a shot. Tim wasn’t afraid of pushing boundaries, and this definitely pushed them.

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With all the letters written, Tim leaned back in his chair and looked at the pile with satisfaction. Harley had no idea what she’d started, but Tim was more than happy to see where it led. He sealed each letter in a black envelope, embossed with a subtle Robin symbol.

Now all that was left was delivery. And in Gotham, nothing stayed secret for long. This was going to be fun.