So... this is just because I love the idea of Tom being the Joker and Harry being Harley Quinn. It's sort of based off of the suicide squad movie, but not really, because this is just them meeting for the first time.

Somewhat inspired by the fics "The Joke Was On Me" by BigJellyMonster and "Puddin', I Kill For You" by Fairygirl34 because that's where I learned of the Tom/Harry and Joker/Harley parallel.

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There was a feeling of anticipation coiling in his gut as he was led through the hallways of Hogwarts Asylum towards his new patient.

He had been extremely surprised when he was offered the chance to work with such a high profile patient, seeing as he was a relatively inexperienced psychiatrist, having only started the practice about a year ago. But, someone seemed to think he was good enough, as he was recommended for this job, and had readily accepted it.

It was the opportunity to get inside the mind one of the most notorious criminals of Hogsmeade city. Tom Riddle. Lord Voldemort. Whatever you called him, he was terrifying, and Harry was about to meet him, face to face.

He tried to keep his face neutral of any emotion, but it was difficult with the excitement and fear warring inside of him as they stopped at their destination and the guard started to unlock the large steel door. It creaked ominously as the guard slowly pulled it open, and Harry gave a nod of thanks before turning towards the room before him.

His patient was already there, seated in a hard metal chair and chained excessively to the table in front of him. Harry approached cautiously feeling the excitement and fear all at once as he got closer. The man had yet to lift his head up from where he was staring down at his lap, and Harry was left staring at the dark brown, slightly curled hair on the top of his head as he sat down slowly on the chair opposite of him.

There was a moment of silence before Harry set his files down and lightly cleared his throat. There still wasn't even a glance up, or any sort of acknowledgement from the man, but Harry continued on anyways. "Hello," he started, and opened the file in front of him.

There wasn't much known about Tom Riddle-aka Lord Voldemort- despite the fact that he was a rather infamous criminal. The picture on his profile depicted him in a sneer, and Harry took a moment to observe the unusual red eyes he had, noting that the file said he had acquired them when he had injected himself with a variety of unknown chemicals in an attempt for immortality. It was uncertain whether or not he had succeeded, as his red eyes were the only thing he currently had to show for the effort.

Harry glanced up at the man and smoothed the papers out on the table. He decided to forgo introducing himself for now and asked the criminal politely, "what would you prefer to be called?" He took a look at his papers once more and then continued with, "you seem to have two names...which would you prefer? Tom Riddle? Lord Voldemort?"

His words seemed to finally get the red eyed man's attention, as he lifted his head up and eyed him critically. "Which would I prefer...?" Harry startled at his sudden liveliness and nodded, looking at the red eyes a picture hadn't seemed to fully capture. They were much more menacing and overbearing in real life.

"Well, that depends on you I'm afraid…" his cold demeanor hadn't faded and Harry shivered at seeing such a malevolent expression on such an attractive face. If it weren't for the blood red eyes and the ominous expression, Harry might think him to be a handsome business man. It was a rather unsettling revelation to find out that the most notorious criminal in the city could walk past him and be mistaken for a normal citizen.

"What do you mean it depends on me? They're your names, I just want to know which one you would like me to call you." He replied cautiously, and watched as his blank face formed into a small smirk.

"Ask me again when we're done here." He said, clasping his shackled hands together and placing them on the table. "But, in the meantime, what is your name, pretty?"

Harry chose to ignore the pretty comment, as well the blush he felt creeping across his cheeks. "My name is Dr. Harry Potter, but you may call me Harry if you'd like." He responded, giving a small strained smile. "I am to be your new psychiatrist, as the last one…"

He trailed off and was given a smug smirk in return. "Ah, yes. The lovely Ginny Weasley. I'm afraid she just wasn't cut out for this… She was broken quite easily. A bit boring too…" Harry shivered at this, hoping to avoid ending up in a situation like Ms. Weasleys. She may not have ended up as insane as the patients she had worked with, but she certainly wasn't sound of mind at the moment, and everyone knew that had to do with her involvement with the man in front of him.

"Yes, well," he said a bit stiffly, "we're not here to discuss Ms. Weasley. We're here to talk about you…"

A cold smile was given in return, though his eyes seemed to portray a small bit of amusement. "Me? You want to talk about me, do you? Don't you want to hear more about dear Ginny?"

Harry tensed at the seemingly playful tone. He didn't want to know more about Ms. Weasley's predicament, nor the part the man in front of him had taken in it. But, when working with violent criminals such as this, sometimes it was better to let them speak about whatever they wished. Sometimes, the criminals even revealed extra information in their ramblings, which is what Harry hoped would happen now.

"If...If you would like to discuss Ms. Weasley, then I am not stopping you. Whatever makes you feel more comfortable." There was a slight creaking sound as the red eyed man leaned back in his chair.

"More comfortable? I'm not sure anything here could be described as comfortable, but I'm sure you'll find my story...enlightening." Harry wasn't exactly sure how to respond to that. He knew that there was absolutely nothing comfortable about the Hogwarts Asylum, but that wasn't necessarily what he had meant.

He decided to refrain from correcting the criminal, and just nodded for him to continue, first asking, "enlightening how?" in a soft tone. He received a small smirk in response.

"Oh...maybe I worded that incorrectly…" he tipped his head back slightly, and appeared to be thinking, and Harry watched on in silence, trying to ignore the pale expanse of skin that was shown as his patient's neck was exposed. After a few seconds, his head lifted back up and Harry was given a charming smile, and burning red eyes that seemed to watch him in a hungry sort of way. "Ah, that's right. It's not so much a story as it is a… warning."

Harry didn't like the sound of that, but was curious despite himself, and this time didn't bother with a response before motioning for him to continue.

"Ginny Weasley…" he hummed, shaking his head slightly. "She was weak. Easily manipulated. There was a fire in her eyes...she had so much...determination. But it was snuffed out so easily, one had to wonder whether or not it had been all for show."

He turned his head back to Harry, his contemplative face morphing back into the harsh critical eyes and studying his carefully blank expression. "I had thought he would have learned his lesson," he whispered lowly, "but it seems Dumbledore is still set on sending the young ones in here…"

His voice seemed to portray a bit of anger, and it burned in his bright red eyes as well. "How old did you say you were Harry?" His name was said softly, and drawn out in hissing like way that made him both uncomfortable and filled with anticipation at the same time.

He answered swiftly, "I didn't say. It is not necessary for you to know my age, just that I am old enough." Their eyes stayed trained on each other, and Harry was about to break the contact and continue the discussion, away from the topic of himself, but suddenly, there was a quiet laugh coming from the man opposite him.

"Oh...I think I like you...you're so much more interesting than my last...friends. Friends, they had called themselves. Said they had wanted to be my friend." Harry watched as his crimson eyes burned with amusement and anger, marveling at the fact that could be so emotive, yet closed off at the same time "I had to wonder if they thought me an idiot...they weren't here to be my friend, they were here to pick at my brain, observe my habits, figure out my past…"

Harry was rather glad he hadn't introduced himself as a potential friend, as many others had done trying to get on his good side. He had been more professional about it, knowing instinctively that the type of person he was to be facing wouldn't take kindly to it.

Speaking with someone who was so perceptive and bitter and insane was fascinating, and Harry wanted to know everything there was to know about the man in front of him. But, he had to ease into the more personal questions, as he knew there had to be at least some semblance of trust built first.

"Why don't you tell me why that upset you?" He asked softly, watching the answering expression raptly. There was something addicting about observing mannerisms of the man, and he could see how Ms. Weasley had been so easily manipulated.

He didn't want to end up like her, influenced by a criminal, used and tossed aside, and he swore to himself that he wouldn't. He wouldn't let himself get sucked into the deceiving whirlwind that was Tom Riddle, Lord Voldemort, whichever. But, sometimes it was rather difficult to remember he was speaking with a criminal, because despite the fact that he was chained and imprisoned, there was still an air of arrogance and power that he seemed to exude.

There was a rattling sound as he shifted in his seat and replied, "If a stranger came and asked you about your past, what would you do?" Harry stiffened at his tone of voice. He sounded as if he knew something. Harry knew there was no way he could know about his childhood, or lack of, but he couldn't help but feel cautious.

"Well," he said slowly, but paused for a moment to figure out what to say.

Though he was interrupted before he could. "Ah, don't lie Harry…" there was a knowing smirk on his face as they looked each other in the eyes and he went on. "It's quite obvious that you were...unloved as a child. It's all over your face, really."

Harry didn't want to admit that he was completely right, as he wasn't even sure how he knew in the first place. Sure, he hadn't had the best home life, but he wasn't sure how he was able to tell from looking at his face. He didn't make it so obvious did he? He had hidden it for years, surely it wasn't so easy for one man to figure it out with just a look.

Neither spoke as they eyed each other carefully, before Harry heard soft whisper from him, "Don't worry Harry, I'm sure not many other people have figured it out. You know the saying, it takes one to know one…" There was a strange glint in his eyes as he said this, he had a strangely amused look on his face, but his eyes were cold and shone slightly with the first vulnerability to be seen.

As soon as he had finished his last word, a bell chimed to signify the end of their session and the guards pushed open the loud steel door, coming to collect their patient.

Harry still hasn't moved, feeling stricken. There was one last whisper from the shackled man before he was dragged from the room. "By the way Harry...Call me Tom…" There was no trace of the earlier emotions shown on his face as the guards pushed him along.

The door slammed shut as they exited, and the noise echoed around the room as Harry sat there, alone. Tom, he thought, as he finally shook out of his surprise. Such a simple name for such a complex man.

…

Tom Riddle had been in the Hogwarts Asylum multiple times. Tom Riddle had also escaped the Hogwarts Asylum multiple times. But, so far, he hadn't been able to get free before getting evaluated by yet another psychiatrist.

It had turned into somewhat of a game for him. For psychiatrists, they sure were easily manipulated and broken, and Tom reveled in the victory of having analyzed and destroyed another person trying to meddle in his life.

They always sent more, though, and so far, they had all been weak. They'd all had youthful faces and optimistic dispositions. It was amusing, yet so very tedious. He wanted a challenge, someone who didn't give in so easily, and quit. Because they had all quit. After about one or two sessions with his mocking sneers and his cold smiles, they hadn't been able to continue. Perhaps they had seen that he was a lost cause.

Of course, the ones that did stay a bit longer, had been easily picked apart by his critical gaze. Faces were so easy to read, and he took full advantage of that. They never really left the session room the same as when they had entered.

So, when he had heard that his last psychiatrist, Ginny Weasley, (she had been determined, but in the end, it was not her learning his secrets, but rather him discovering and exploiting hers) had finally given up, he felt smug, for having driven away yet another meddler, but still rather upset. First of all, because he was stuck in a shithole. Second of all, because he knew they would just send in another generic psychiatrist with an annoying smile that disappeared within the first five seconds. He was getting bored in here, and he just wanted out.

But, then, his new psychiatrist walked in. When he first heard the door slide open, he didn't even bother to look up. He knew what he would see. When his psychiatrist spoke up though, he was surprised to hear a deeper voice that obviously belonged to a male.

They usually sent women in for him, which he had guessed was because they thought he would respond better to them. But, to him the gender of the person attempting to evaluate him didn't matter. To him, they were all just people, all looking for the same thing, just going about it in different ways.

He still hadn't looked up at his first "hello", though. He wanted to build the suspense. His new psychiatrist might have had a professional tone, but there was still that underlying hint of fear that Tom loved.

There was some shuffling, and then, he asked an unexpected question. He wasn't usually asked it- which name he preferred-but, when he was, he usually responded with a stiff response of, "Voldemort will do."

This time though, as he studied his new victim's face, he knew it would be different. There was a strange air of naivety around him, as well as maturity, which was contradictory and all together confusing. For a second, Tom had thought he was reading the man wrong. But, no, Tom didn't make mistakes, and the genuinely curious and kind, yet stiff and wary posture of the man in front of him didn't lie either.

It was fascinating, and Tom had taken a second just to observe his rather attractive figure before replying. The following conversation was one of the most interesting he had had in a long time. His doctor-Harry, was his name, such a plain name for such an interesting man-was a very open book. He wore his heart on his sleeve, and Tom was vaguely disgusted at the simplicity of it, yet intrigued by what it revealed.

Harry's bright green eyes shone with kindness and vulnerability, but his posture screamed with obedience and fear. There was a soft and curious look on his face, and a small unsure frown on the corners of his lips. It hit Tom suddenly, that this man was like him, but not. Two sides to the same coin, similar upbringings different outcomes.

Tom was immediately hooked. This wasn't a toy he would be throwing away anytime soon, because while his other playthings had been fun, Harry was so obviously special. Harry was meant just for Tom, and Tom was going to have him.

...

I wasn't actually sure if I was going to post this, because it's horrible... I tried to fix it because there's something about it that just doesn't sound right, but I couldn't figure it out...

So, if you see what's wrong with it, please comment and tell me what it is. It's bothering me so much...

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Was originally a one shot, but I've decided to continue it as a multi chapter fic...