A/N: Welcome! This is quite possibly, Edward Nigma's nightmare. The premise is rather simple. Edward has forty-four rules to surviving Gotham's criminal underworld and each one comes with a lesson learned. The majority of these are funny one-shots, but they aren't exclusively for giggles. We've got Smug Edward, Cop Edward, Rogue Edward, something for everyone. Depending on my mood. Rules #1-#5 pertain to Edward Nashton before and during his transition into the Riddler. After that, it's a free for all.

Dead Switch, the faithful Riddler lackey will be giving her thoughts on the lesson at the end of the chapter as anecdotal commentary.

#1 Take the simplest route out of a building.

Oh well. This was just fantastic. Brilliant. All he needed. Who the hell knew that taking the left door instead of the right one would lead him the complete opposite way he wanted to go?

Do people know how to properly plan a building or are all architects constantly high? Well… this was a Pinkney building. It could be argued the man was strange before drugs entered his life. Just what is his fascination with Gargoyles? The bloody things decorate his buildings inside and out! It beggars belief!

A noise, the clattering shift of a bottle alerted him to their presence. Ugh. How utterly predictable. Gotham's finest. And now he was lost. In a Pinkney building. With some beat cops. The kind that shoot first and explain away the dead body later. He knew they did. Sometimes he helped them cover it up.

This was supposed to be a simple entrance and exit through the building to scout for possible server points but now, he'd hit a wrinkle.

The room appeared to be most recently used as storage. Containers and boxes piled towards the ceiling blotted most of the moonlight that shone through the high windows. Well, there was his escape, now if only he had enough light with which he could find his starting point-

'Musta been a false alarm Jim. There's no-one here.'

'The witnesses-'

'I don't care what the witnesses saw, witnesses never agree-'

He stood and fumed as the voices lazily drifted towards him. Of course the one time he was hoping they would be too stupid and lazy to bother with a proper investigation, they did.

His eyes restarted their search for a low point when the clouds above Gotham parted and illumined a heavily soiled and dust covered cloth overlaying something large.

Curiosity got the better of him and he approached. The cloth was stiff with dirt and effectively ruined his clothes but that took secondary precedent to the more pressing need not to be caught. The first few tugs barely shifted it, but the more it moved the easier it became until the cloth flopped to the ground and sprayed him with dust and mould.

For a second, he was blinded by the light that shone back at him and desperately tried to cover his watering, stinging eyes.

'-Can't we just file a section three "Unfounded Report" and call it the end?'

'Not until we search the entire building Frank. Those're our orders.'

'Shit, that'll take forever.'

As his eyes adjusted to the harsh light, he realised he was staring at his own reflection. Two brilliantly blue eyes shone out from a pale, almost grey face streaked with dark lines of dirt. Brown hair, bleached of all but a shred of colour stuck up at odd angles, coated finely in specks of dust. His glasses, while normally unused thanks to vanity issues were also obscured with particles. A lithe, slim frame turned this way and that as he examined the state of his favourite outfit.

Edward Nashton sighed. Frankly this wasn't how his criminal career was meant to be going and while he had expected parts would be grimy and certainly messy, he hadn't expected to be chased so far and so fast, not by the GCPD.

He suppressed a laugh. He was being chased by his own employers. There was irony.

Just why was this here? With the beams now scything through the darkness, he caught the edge of a stamp across a dusty box. Haly's Circus. Of course, this was being used as overflow storage. Moonbeams scythed through the darkness that interspaced the boxes and Edward found a likely looking box just the right height to climb. It wouldn't reach the window but all he had to do was climb the escalating pyramid of wooden frames to the window and freedom would be his.

The boxes were, if possible, filthier than the cloth of the mirror had been. He didn't care though. Within minutes he'd closed in on his escape route. Maybe next time they'll catch me. He thought as the knee of his favourite suit tore thanks to a badly placed nail. His shivering skin felt fat snowflakes as they lazily fell from the heavens. He snorted as he reached out to push the freezing glass further open. I doubt that.

The shocking boom of a discharged gun rattled him as a chunk of plasterwork was effortlessly blown from the wall. 'Thought I didn't see you, bastard?!'

The sudden imbalance of weight all but caused him to slide headfirst out of the window. He owed his postponement with the ground to a well placed nail that had caught the torn fabric on his knee. Ominously, it was still tearing. It didn't take a man of his intellect to see what was going to happen next.

He dropped painfully into a snowdrift.

Well fuck.

Now he was filthy, cold and wet. At least he hadn't been caught yet. That was the main thing. He could put up with some mud and blood to get away scot free.

'Hey- I heard something from outside!'

'He's somewhere out there!'

The voices drifted out of the building and down to him effortlessly and he idly anagrammed a curse.

Being a criminal was a lot more frustrating and annoying than he'd every thought possible but as his bloody knee twinged and his back ached as he lurched into the darkness again, he had to give a small smirk.

They had no idea what was coming.