Author's Note: Ok, so this is my first fanfiction published on this site, so I'm very new to how this works. Any and all (constructive) criticism is appreciated. Please keep flames down to birthday candle level!

Anyways, I'm a huge Riddler fan, because I feel that there's something about him that is different than most of the other rogues, hopefully I can convey this to you effectively.

Disclaimer: I own nothing, anything you recognize, or think you recognize is not mine except the lovely Doctor Allison Capuano. I make no money off this. If I owned The Riddler I would be a very happy girl.

And thank you for reading!

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Part I

Regret is mainly felt by two groups of people. First, there are those who didn't do anything spectacular with their lives. There were things they wished they'd done, jobs they wished they'd taken, people they wished they had loved, and the main questions that fill their minds usually begin with "What if…" They spend their lives playing it safe, and end up wishing they hadn't.

The second group is nearly the opposite, as it is full of those who live life a bit too wildly. They never thought twice about anything they ever did, and try not to look back, because sometimes, their pasts are just too gruesome. Their lives are full of risks taken, friends lost, and more than a fair share of mistakes.

And while they are on opposite ends of the spectrum, they both, in the end, share the immense feeling of remorse, wishing they had lived their lives differently.

Allison Capuano was part of our first group. All of her life, she had just blended into the background. In high school, she had skirted through her four years, maintaining an 87 average, graduating with only her group of friends really knowing her. She went on to medical school, despite really wanting to study art, and finally received her medical degree, and she got a job at Gotham General Hospital, playing it safe, as always.

Dr. Capuano was known throughout the hospital as being immensely nice, and even more as unable to say no to anyone. Another interesting piece of gossip concerning the good doctor was that she was irrevocably in love with her colleague Doctor James Wilder, although it was known that she was much too timid to ever act on it. Instead, she silently admired him, hoping that one day he would realize it, and feel the same for her. But she'd never act on those feelings. No, not when he was so… intimidating. That perfect jaw line, pouty lips, deep green eyes… I could never…

"Allison?" He was speaking to her. Talk dammit! He smiled patiently waiting for her response.

"Erm… yes James?" She nonchalantly placed the files for her patients on the counter, and pushed dark bangs out of her eyes.

"I know this is quite last minute, but would you be willing to cover my shift tomorrow? It's the midnight to noon shift." Midnight to noon… after my noon to midnight that day. Allison knew what she was going to say, despite her better judgment.

"Sure James…" She smiled pleasantly. A full twenty four hours at the hospital was going to be torture. But she really couldn't resist those eyes of his. I need to grow a backbone. She mentally scolded herself, and decided she'd go home and rest before a long double shift ahead of her.

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Is it legal to work 34 hours straight? Allison wondered to herself, peeling off her sweaty, bloodstained scrubs. I hope so… She glanced at her watch; it was almost 10:30. She groaned. The first twelve hadn't been too bad, the second twelve dragged a bit, and then, an hour before her double shift ended, all hell broke loose in Gotham. Within an hour there were fourteen injured from a gang fight, three random knifings, two car accidents, and around thirty civilians sick with fear from the Scarecrow's latest crime spree. After an additional ten hours of stitching, surgery, and administering antidotes, Allison's boss Lisa Craig had pulled her aside.

"How long have you been here?" Her voice was serious, yet concerned. Lisa arms were folded in business mode and her foot was tapping impatiently.

Allison, dazed at this point, held up fingers pretending to count the hours, even though she knew the exact amount. "Thirty-three hours and forty-five minutes," She mumbled.

Lisa's jaw dropped. "How many?"

"Almost thirty four," she managed to gasp out, rolling up the sleeves of her worn scrubs.

"Go home." Lisa placed a hand on her shoulder. "You're overworking yourself… and for what? James would be lucky to have you. You don't need to do him any favors." She had lowered her voice.

"What makes you think this is about Ja- Doctor Wilder?" Allison stated as professionally as she could manage.

"I'm the dean of medicine." Lisa rolled her eyes. "I know everything. Now, go home." And with that, Lisa had shooed her into the locker room.

After a brief hot shower, Allison pulled on her favorite sweat pants and was finally on her way home. Well… if she could find her car that is. It made her nervous, wandering around the deserted hospital parking lot at eleven o clock at night, searching for her car. You would think it would be easy to locate a sunny yellow Volkswagen beetle, but not when you couldn't remember which floor you had parked on. Allison groaned. This was going to take a while.

She was on the third floor of the parking garage when she spotted it, all the way at the other end of the room. Feet don't fail me now. She pleaded, becoming increasingly tired with each step. Allison paused for a moment, to catch her breath, and could have sworn she heard the sound of footsteps continuing after she had stopped walking.

"Hello?" She said out load. Living in Gotham all her life, Allison was a very superstitious person; you had to be when there were at least a dozen famed super villains who would kill you as fast as they would look at you.

Shaking off the thought, she finally approached her car, fumbling to get her keys in the lock. She opened the door, and smelt the faint smell of some sort of chemical somewhere behind her. After that, everything went black.