Chapter 1 – The Riddler
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Rose let out a weary sigh as she stepped out of the glass and steel doors of the Wayne Enterprises building. It had been a long day at work as the marketing coordinator, promoting the company's various products and philanthropic initiatives. Though she loved her job, Rose found herself longing for more friendship and community in Gotham City at the end of each day.

She had moved here a month ago, after coming across the listing for her role online and impressing Bruce Wayne himself during a lengthy phone interview. It was nice to leave behind her small hometown, where she felt like she had outgrown the limited career opportunities and familiar faces she had known since childhood.

Her closest friends from high school and college were now scattered across different states, busy building their own lives and careers. They tried to keep in touch through group chats and occasional phone calls, but conversations had grown more infrequent and superficial over the past few years. Rose had hoped moving to a new city would give her a fresh start to meet new people and form meaningful connections, but that had proven harder than expected.

Her coworkers were friendly and professional, but they didn’t seem interested in getting to know her better. They mostly talked about work-related topics in the break room or exchanged brief greetings and compliments. Rose tried initiating conversations about hobbies, interests, or personal stories, but they often ended abruptly or awkwardly.

Tonight, one of her coworkers had finally agreed to meet up for drinks after work at a nearby happy hour spot. Rose was looking forward to relaxing over cocktails and getting to know her coworker outside of the office. 

But just before leaving, the coworker canceled last minute. Rose tried not to let the disappointment show as she gathered her belongings alone like she had every other day for the past month. It seemed making friends in Gotham would not be as easy as she hoped.


Rose strode quickly towards the parking garage, the echoes of her heels slapping against the concrete floor. All she wanted to do was get home, remove these damn shoes, and collapse on the couch watching her favorite tv programs.

She reached her old gray Civic and slipped the key into the ignition, but the engine just clicked emptily in response. She tried again, pressing down harder on the gas pedal as if that would magically make a difference. Still nothing.

"Shit!" Rose pounded her palm against the steering wheel in frustration. The night was falling fast, and this part of town wasn't somewhere she wanted to be stranded after dark.

She grabbed her phone to call roadside assistance, but the screen was black. "Of course, the one time I need it..."

Throwing the useless phone into her purse, Rose took stock of her limited options.

The parking garage was emptying as the evening rush hour ended. Soon she'd be the only one left here alone. She didn't fancy waiting in the car, a sitting duck for anyone lurking in the shadows.

Her eyes scanned for the nearest payphone she could use. There was a run-down gas station a few blocks away that might have one. It wasn't ideal, but it was better than staying put.

Rose exited the car and threw her bag over her shoulder. With a deep breath to steady her nerves, she stepped out into the fading light and started the long walk to find help.

As she began walking down the street, Rose felt a growing knot of anxiety in her stomach. Gotham had a notorious reputation for danger, especially once night fell on the crime-infested streets. 

With her petite frame, long chestnut brown hair, and matching doe eyes, Rose knew she made an easy target for the city’s violent criminals lurking in the shadows. She quickened her pace, hoping to avoid any sinister encounters.

Suddenly, a gravelly voice called out from a narrow alley to her right. "Well well, what do we have here? A little lost mouse scurrying home?"

Rose whipped her head towards the sound and saw two thugs emerging from the darkness. She stumbled backward in alarm, only to collide forcefully with two more men who had been concealed behind her. They seized her roughly by both arms, their fingers digging painfully into her skin.

"Please, just take my purse and leave me alone!" Rose pleaded desperately, heart hammering in her chest.

"Oh we'll take more than just your purse," one of the men leered, his hot breath on her neck.

Rose felt paralyzed with terror. She squeezed her eyes shut and whimpered involuntarily. Her heart raced so fast she thought it might burst from her chest.

Through the rushing in her ears, she heard a faint, eerie sound in the distance - a sing-song voice echoing down the alleyway. The men froze, exchanging wary glances as the voice grew louder.

"Riddle me this, riddle me that. Who's afraid of the big black bat?"

Rose forced her eyes open and peered upwards. A shadowy figure was perched high above on the ledge of a building, backlit by Gotham's murky glow. He was clad in a green suit and a purple question mark tie that looked wildly out of place. A matching green domino mask concealed his face, and he gripped a golden cane capped with a question mark symbol.

She stared in bewildered confusion, uncertain who this bizarrely-dressed man might be. He clearly had theatrical flair, but she had no context for his strange costume and sinister-looking cane. Was he a friend or foe? Another criminal that came to threaten her?

As the green-suited stranger dropped down into the alley gracefully, Rose shrunk back warily. But he ignored her cowering form, turning his attention fully to her rough captors. 

The largest thug stepped forward aggressively. "Scram, creep, before-"

"Tut tut, such rudeness." The green-suited man cut in with an oily smile. "I merely wished to play a game. But it seems you gentlemen have...prior engagements..” 

The thug sneered in contempt, puffing out his broad chest. "We ain't got time for yer stupid mind games. Beat it!"

The man’s smile didn't fade, only widening with secret delight. “As you wish. But first...”

Without warning, he flung a small dart from his cane directly at one of the thugs. The man let out an agonized cry as the poison rapidly coursed through his bulky form. He collapsed to the ground, writhing and clawing desperately at his flesh.

"Johnny!" the others yelled in panicked alarm, instinctively dropping to their knees at his side.

"Your large friend has precisely ten minutes before that specialized concoction ceases his heart," the man casually explained, glancing idly at a pocket watch produced from within his emerald suit. 

"Answer my riddle correctly within the time limit, and I shall administer the antidote to neutralize his poison. However, refuse to engage or answer incorrectly, and Johnny dies."

The panicked thugs looked at one another with fear in their eyes, taking in Johnny's racked whimpers and spasms below. They realized with dread that they had no real choice left but to play along with the deranged criminal's deadly game if they wished to save their friend from a most gruesome demise.

The largest thug sneered up at the green-clad newcomer through bared teeth. "Fine, we'll do yer damn riddle. But Johnny here better still be breathin' after!"

"We shall see!" the man exclaimed with creepily theatrical glee, "Now then, riddle me this - what has roots as nobody sees, is taller than trees, up, up it goes, yet never grows?"

The thugs racked their brains frantically, throwing out wild guesses to the bizarrely dressed man between panicked glances at Johnny.

"The sky?"

"A tree?"

"Clouds?"

He merely chuckled as he inspected his watch. "Tick-tock, time is running out," he sang, his eyes wild with twisted excitement.

Finally, the largest thug lost his nerve. "To hell with this!" he spat, spinning on his heel to make a mad dash for the entrance to the darkened alleyway, hoping to bolt for safety while they still drew breath.

His remaining cohorts scrambled after him, only to stop mere feet away with gasps of horror. Somehow the man in the green suit now stood calmly blocking their only route of escape, having managed to slip in a blur between them without a sound.

"Uh uh uh," he tutted, wagging a gloved finger. "You're not going anywhere until you solve my puzzle."

They knew with dread that stalling would avail them nothing now. The thugs launched themselves at him, but he easily sidestepped their brutal assault. With a flick of his cane, he swept the legs out from under one attacker. 

As the thug crashed to the ground, the green-suited man spun low and struck another in the chest with a precise jab, forcing the breath from his lungs in a pained whoosh.

The last thug charged with an angry yell, swinging his fists fueled by fear and rage. The costumed man dodged each blow with mocking grace, teasing the thug ever closer to exhaustion. When an opening presented itself, he sprang into action. His cane whipped around to crack against the thug’s temple, dropping him into darkness.

Straightening his suit with a few brusque pats, the man surveyed the fallen thugs with lidded eyes. "It seems our time is up. Pity you didn't guess...a mountain.”

Rose watched nervously as he stepped over the fallen thugs carefully, spinning his cane expertly. She felt torn by uncertainty over her green-clad rescuer’s motives and true nature.

On the one hand, he had clearly mastered those brutes with cunning and grace when he could have simply walked on by. Yet there was an undeniable menace radiating from him - the cruelty in his smile as he poisoned one attacker, the wild excitement in his eyes as he manipulated them in his lethal game.

Rose bit her lip anxiously as his piercing gaze finally settled onto her cowering form. She recoiled instinctively when he closed the distance, his tall frame looming over her. Nervous tears gathered in her eyes as he stared down at her.

"My dear lady, are you alright?" he inquired, tone laced with concern as he approached. "Those foul miscreants didn't harm you I hope?"

Rose shook her head warily in reply, still wrestling with conflicting relief over being rescued and residual fear toward her enigmatic savior who had descended from the darkness. 

"Ah, it relieves me to see you unscathed," he proclaimed. 

Removing his bowler hat with a flourish, he gave an elegant bow. "Allow me to introduce myself. I am Edward Nygma, known in less reputable circles as The Riddler. Roguish genius and virtuoso of puzzles at your service."

He extended his hand graciously. "And whom might I have the honor of addressing, my dear?"

Rose hesitantly placed her hand in his. "I'm Rose. And...thank you for helping me, Edward.” She tried to keep the tremor of lingering fear from her voice.

"My pleasure, Rose," he said suavely, bringing her knuckles to his lips in a show of gallantry.

Rose gently pulled her hand back, still hesitant to let her guard down. She knew little of his true motives in her rescue.

Noticing her wariness, Edward adopted a reassuring tone. “You’ve nothing to fear from me now, my dear. You have my word you will come to no further harm in my company tonight.”

Though still guarded, Rose found herself believing the sincerity in his intense gaze. Gotham's most cunning criminal mastermind had no reason to offer protection if he intended her ill will. She would have to trust him, at least for now.

“Now then, what brings you out alone into Gotham's treacherous nights?” Edward inquired.

"My car broke down a few blocks over," she explained, averting her eyes self-consciously. "I was trying to walk to the nearest gas station for help when those men grabbed me. I guess you know the rest..." she trailed off.

Edward listened intently, his keen gaze sweeping their dingy surroundings. "My dear, Rose, as the one who disrupted those thugs in their nefarious ambush of you, I consider it my duty to ensure you make it home safely. The risk of further misadventure is too great should we part ways here.”

Rose bit her lip, hesitating. She hardly knew this eccentric man, but she knew he was right. It was too dangerous for her to walk home alone after what happened. "Thank you, I think I would feel safer with an escort," she replied.


As they navigated the twisting back avenues, an unlikely rapport grew between the pair. Rose couldn’t resist sly side glances at his sharp profile beneath the brim of that jaunty bowler hat. Her unlikely savior cut a striking figure with his lean athletic build, stylishly framed by that meticulous emerald suit.

Noticing her subtle attention, Edward met her gaze directly. The intensity of those keen green eyes behind his mask made her blush at being caught out.

“So Rose, might I trouble you to share some of your personal story?” he queried. “What is it that occupies your days in Gotham?”

Rose hesitated, but his expression radiated genuine interest. She reminded herself that he had proven trustworthy so far that night.

“Well, I work over at Wayne Enterprises in marketing,” she offered shyly. “I’m originally from a tiny rural town hours outside the city. There weren’t many job options there, so I took a chance moving here. A fresh start, I guess.”

Edward nodded along thoughtfully.

Rose continued opening up, compelled by his attentiveness. “I enjoy my work, but making actual friends has been tough." She exhaled softly. “Back home, everyone knew their neighbors. Here, people just come and go without much more than polite smiles or short chats.”

"Ah, I understand such isolation all too well," Edward acknowledged sadly. "As a boy I found myself scorned and rejected for my high intellect," Edward explained. "My ravenous curiosity intimidated dull minds."

"That must have been really isolating growing up," Rose replied sympathetically.

Edward nodded. "I eventually found some solace in stimulating puzzles and engineering elaborate schemes, but the social connections I craved always remained out of reach."

He glanced over at Rose. "That is, until our chance meeting tonight."

Rose felt touched by his openness. "I know what it's like to feel different. To have people misunderstand you or brush you off," she admitted.

"Indeed, such isolation can gnaw at one's spirit," Edward acknowledged.” 

He gave Rose a grateful smile. She returned it warmly, the growing bond evident between these two lonely souls finding an unlikely connection.

Their conversation meandered through hobbies, interests, and amusing anecdotes from their respective pasts. Rose felt herself open up more than she could remember doing since arriving in Gotham. For the first time, she didn’t filter her quirky observations or small-town stories. Edward listened with flatteringly rapt focus no matter the subject, interjecting insightful questions or witty remarks that made her giggle.

Before she fully registered their surroundings, Rose realized they had reached the steps of her apartment building. She hesitated, almost reluctant for their unexpected but pleasant walk to end. Facing Edward, she tucked a stray lock of hair behind one ear self-consciously.

“This is me...Thank you again for everything tonight, Edward,” she said. She met his striking eyes as she added sincerely, “It was really nice talking to you.”

Edward graced her with a courtly bow. “The pleasure was all mine, my dear.” 

Straightening slowly, he captured her hand and raised it boldly to his lips. The contact sent an unexpected tingle up her spine even through his gloves.

“I do hope our paths cross again someday,” he murmured, eyes glinting playfully. His voice dropped intimately. “I confess I really enjoyed your company this evening.”

Rose felt a thrill at the intensity of Edward's gaze. His words hinted at possibilities she hadn't considered. Something told her this unexpected meeting was just the beginning of unknown adventures ahead with this enigmatic man.  

With a wink, Edward released her hand and took a step back. "Until next time, my dear," he said mysteriously before melting into the shadows of the night.

Rose watched him walk away, skin still tingling from his touch. She sensed there was more to the Riddler than his showy persona let on. And though she barely knew him, she found herself wanting to uncover those hidden depths and solve the puzzle that was Edward Nygma.

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