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The Grandmaster of Magical Paperwork and His Petulant Teenager

Summary:

Harry Potter was ninety percent sure that magical law enforcement was built on a foundation of cruel and unusual paperwork.

Then a suspicious Horcrux landed on his desk.

One terrible decision later, Harry finds himself trapped inside Tom Riddle's diary in 1945, facing a nineteen-year-old Dark Lord who is far too ambitious, far too attractive, and currently employed at Borgin and Burkes.

Escaping should have been simple.

Unfortunately, Harry accidentally convinces Tom that Siri is an ancient deity known as the Woman of Knowledge.

Things go downhill from there.

Notes:

(See the end of the work for notes.)

Chapter Text

Harry was ninety percent sure that the entire platform for magical law enforcement was built purely on a foundation of cruel and unusual paperwork. It was past midnight, the tea on his desk had gone completely cold, and he was currently staring down a mountain of incident reports that made him want to launch himself out of the nearest window. He rubbed his eyes, the frames of his glasses digging uncomfortably into his nose, and let out a long, pathetic groan.

Two more hours until he could get the hell out of here.

Then came the sharp, demanding clack of a beak against his office window. As he looked outside, a flurry of feathers pathetically slumped itself on the external windowsill.

Crap, Harry had left his windows closed again. Poor Ministry owl, he thought, hoping it didn’t die anticlimatically like the last one that collided with his office windows.

Rushing towards the window, Harry rescued the creature, who was terribly unhappy, and placed it gently on his desk.

The owl was not pleased, and made it apparent by crapping all over his paperwork.

Splendid.

Cleaning up the bird mess with a lazy Scourgify, he unrolled the urgent memo from the Department of Mysteries. The ink on the official Ministry stationery was literally trembling, the letters vibrating against the page as if they were trying to escape.

Subject: Horcrux (Black Leather Notebook). Status: Unstable. Recommending immediate Auror intervention. Harry stared at the trembling ink, a bad feeling pooling in the pit of his stomach. It couldn’t be that leather notebook… 

He sighed, throwing his quill down. "Brilliant. Just brilliant."

Ruffling up the poor bird's feathers, Harry groped around before locating a small package tied to the owl’s leg.

He was practically blinded by the neon yellow warning labels plastered across every inch of the packaging.

Yep, it was definitely that notebook.

“We meet again, Tom Riddle” Harry deadpanned to the package.

The package did not offer him a response, as it was a package.

Unwrapping it slowly, Harry took out the book that he had brutally stabbed in his second year at Hogwarts.

“Heh.” he snickered, remembering how he had overpowered The Dark Lord as a twelve year old schoolkid. 

Poking and prodding at the gaping hole in the middle, Harry was confused as to what instability it could possibly be showcasing.

Setting it on his desk, he quickly cast a few protection charms to make sure the angry soul of Lord Voldemort won’t assassinate him while he was on his job.

That would totally knock him out of the best employee competition. Harry glanced at the neon yellow post-it notes cluttering his desk, then at the owl that was currently making itself at home in his office.

Harry grabbed the Ministry owl and threw it out of the window.

“Bug off, I’m busy.” he shouted at the angry, overworked owl, before realising he and the owl shared a lot of similarities.

Harry picked up the cursed artefact with his bare hands.

It was a book. A book that contained the soul of a dark wizard, sure, but hadn’t Harry already removed the soul fragment like he was starring in The Exorcist years ago?

Better to be safe than sorry… Harry decided, opening the book to an empty page, which was quite difficult due to the disgusting hole in the middle.

Picking up his battered old quill, Harry paused, hovering inches over the book.

Should he really be writing in this? What would happen? Would there even be a response?

Harry was not prepared for the possibility of being ghosted by The Dark Lord.

After an unnecessarily long internal debate, Harry settled on the short and sweet.

“Miss me?”

“What?”

Harry paused, unsure whether to laugh at the fact that The Dark Lord responded to a romantic-sounding line like that or to be concerned at the fact that there was a response in the first place.

He glanced down at the words on the page, disappearing slowly.

Interesting. 

Unlike how he remembered it, the ink slithered across the paper before finally disappearing into the pages. 

Must be an aftereffect of the Basilisk venom.

New words appeared on the page.

“Stop fooling around with this book, you have been warned.”

Harry stared at the letters on the page, written slightly differently from how he had remembered it.

“Hello Tom, how are you?”

Yes. Always inquire about the well-being of the person you are speaking to. Basic courtesy is a must, thought Harry Potter, the upstanding citizen.

“What do you want with this book.”

Ouch, how rude.

“May I come in?”

The ink slithered across the page, finally disappearing.

No response.

Harry Potter, The Boy Who Lived, ghosted by a fragment of The Dark Lord.

How sad.

Not even his sad love life had seen such a pathetic ghosting as this. Pride wounded, Harry reached out to close the book, only to pause at new words slowly emerging from the page.

“You want to come inside? Fine.”

Well that would have been explicit if taken out of context. Harry chuckled to himself, as if he was the world’s best stand up comedian, before inching closer to the book. Where the hole left by the Basilisk should have been was a gaping void of ink. 

Harry gingerly extended one finger into the expanding ink hole. The ink took that as an invitation to continue, spreading up his hands, enveloping him whole.

The whole thing took less than a few seconds, giving Harry barely any time to react.

Before he knew it, his vision was blurry and he felt as if he was being pierced by a thousand knives.

Death by a thousand cuts? He mused as his consciousness slowly slipped away.

***

Groaning loudly, Harry pushed himself up from the freezing, damp ground, spitting out a mouthful of dust that tasted suspiciously like old parchment. His spine popped uncomfortably, and his muscles ached as if he had just survived a rogue Bludger to the ribs.

He blinked his vision into focus, adjusting his glasses, and immediately went on high alert.

"What the hell..." Harry muttered, looking around.

He was standing in the middle of a completely deserted cobblestone street. It looked like London, but everything was slightly wrong. The sky above him wasn't blue or grey; it was a sickly, pale yellow color, and the clouds looked like stationary blots of black ink frozen in mid-air. There was no wind. There was no sound. There wasn't a single soul in sight.

"Brilliant," Harry snapped, brushing the grime off his Auror robes. "Absolutely spectacular. Sucked into a cursed diary because I couldn't handle being ghosted by a teenager."

Fuming, he checked his pockets. Thankfully, his wand was still there, tucked securely into his holster. He pulled it out, holding it ready as he marched down the street, trying to find a recognizable landmark. If this was a memory of London, then Diagon Alley had to be nearby. He just needed to find the entrance to the Leaky Cauldron or the brick wall behind the dustbins.

Avoiding puddles on the street that looked suspiciously like black ink, he turned a sharp corner, expecting to see the bright, bustling storefront of Quality Quidditch Supplies.

Empty. A ghost town.

There was only one place that would be empty at this time of the day. Harry looked up at the nearby walls.

The street name painted on the side of a dingy brick building read: Knockturn Alley.

Harry stared at the sign with an expression of such disbelief that you would have assumed Shen Qingqiu transmigrated into Harry instead. All he was missing was a paper fan to hide his absolute disgust at the "System" that had dropped him into this mess.

If a mechanical voice started ringing in his head right now telling him he was losing OOC points, he was going to snap his wand in half.

Of all the places the book could have dragged him, it had to be the sketchiest neighborhood in magical Britain.

"Right," Harry muttered to himself, adjusting his glasses. "First order of business: figure out when the hell I am."

His immediate thought was Hogwarts. If this diary was a time capsule of Tom Riddle’s memories, then a teenage version of the Dark Lord was probably currently brooding in the Slytherin common room or terrorizing the library. Harry groaned aloud at the prospect of having to trek all the way to Scotland just to interrogate a dramatic sixteen-year-old.

“All because some stupid little kid didn’t go to therapy,” he spat. He was working overtime, in a magical book, to capture a teenager who couldn’t regulate his emotions.

He started pacing down the alley, looking for any indication of the date. He was about to give up and call it a day, except he had no idea how to escape Tom Riddle’s old therapy diary. 

Groaning, Harry scanned the walls that were textured like old hard parchment paper, before his eyes landed on a promotional poster.

Half price for selected goods on July 17th, 1945!

1945.

Harry blinked.

Tom would be around nineteen years old this year. There was no point in going back to Hogwarts if he had already graduated!

“Brilliant,” Harry deadpanned to absolutely nobody in the dingy alleyway. “He’s not a schoolkid anymore. He could be absolutely anywhere in this darned country.”

Harry wracked his brains for absolutely any piece of information that could help him locate this elusive future criminal.

Then the pieces clicked.

According to Dumbledore’s lessons, he could only be in one place as of now…

Harry slowly turned around, his eyes locking onto the weathered wooden sign hanging just a few meters away: Borgin and Burkes.

"He's working here," Harry realised, a deeply amused smile spreading across his face. "The future supreme dark lord of Britain is currently working a dead-end retail gig."

Suddenly, the terrifying prospect of facing the Dark Lord felt a lot less intimidating. Armed with the knowledge that his ultimate nemesis was probably dealing with annoying customers and dusty shelves, Harry marched straight toward the shop door, ready to see it for himself.

With a heavy, suffering sigh, Harry gripped the brass handle of Borgin and Burkes and pushed it open, the little bell above the door chiming with a hollow ring.

The interior of the shop was just as frozen in time as the street outside. Dust motes hung suspended in the pale, stationary light, and shelves stretched up to the ceiling, packed with shriveled hands, blood-stained playing cards, and staring glass eyes.

But what really caught Harry’s attention wasn't the dark artifacts. It was the figure standing behind the polished glass counter.

Tom Riddle looked immaculate. His hair was perfectly parted, his robes were pristine, and he was currently polishing a silver chalice with a cloth. Hearing the door, he looked up, blinking his dark eyes in mild surprise before his face instantly smoothed out into a practiced, dazzling smile that oozed pure compliance.

"Good afternoon, sir," Tom said, his tone smooth, polite, and horrifyingly professional. "Welcome to Borgin and Burkes. How may I assist you today?"

Ugh. Creepy creepy creepy! Stop pretending that you aren’t a creep! Harry panicked internally.

However, he could not call current Tom Riddle a creepy creep, and instead settled on an awkward smile back, well aware he was not even half as charming as the man in front of him.

“Nice shop you have, mate,” Harry cringed. What the hell was he talking about?

Tom flashed him another dazzling, polite smile, before inquiring gently, “Are you here to buy or sell? Or are you perhaps lost?”

No, I’m not lost, I’m trying to find a way to get out of your little murder book!

Harry stared at Tom, his social skills failing him terribly.

Tom glanced at Harry suspiciously, taking in his very modern, or to him, eccentric attire. “Where do you hail from, sir?”

“What? Oh. I am, uh, British. But not fully British! I’m half British and half Chinese. From a country far away, you wouldn’t know it.” It was glaringly obvious each sentence was pulled out from his ass.

However, Harry continued, as if his introduction did not sound wholly made up.

Tom stared at him for a while before offering him a response “I see, please enlighten me, where exactly do you come from? You sound so local after all.”

Harry was on the verge of tears. Stop asking me the hard questions! I haven’t had my coffee yet, you buffoon!

Harry immediately brainstormed internally.

Okay, it is 1945. I sound British. I am French-Japanese. That diversity could be found in places such as… Singapore!

Oh no, Harry thought, as he realised Singapore did not exist as Singapore right now.

It was 1945 and Singapore wasundertheJapaneseruleandwasnamed Syonan-to! Yes, he was from Syonan-to.

“I am from Syonan-to.” he said, finally.

Tom stared at him, “I see, it’s a wonder how you escaped the war and fled to Britain. You must have blended right in with the British returning here, you don’t look very Chinese.”

Harry nodded, agreeing enthusiastically. Yes! Believe me, please!

“But sir, this is Borgin and Burkes. Are you buying or selling? Or I’d have to ask you to leave.”

`

No! No no no! You are my exit ticket from this stupid notebook!

Harry needed to interest The Dark Lord into continuing a prolonged conversation with him.

Harry’s brain short-circuited. Think, Potter, think! What does a nineteen-year-old psychopath working retail actually care about? Power. Dark magic. Items he can steal from his employers.

“Actually,” Harry blurted out, leaning heavily against the glass counter to look as casual as possible, despite the fact that his heart was hammering a frantic rhythm against his ribs. “I’m not here to browse the discount section. I brought something with me. Something extremely rare from back home.”

Tom’s eyes narrowed slightly, the corporate, dazzling smile dimming just a fraction as genuine curiosity took over. He set down the silver chalice and the polishing cloth, his long, pale fingers resting elegantly on the glass counter.

“From Syonan-to?” Tom inquired, his voice dropping into a smoother, lower register. “The Far East has always possessed... fascinating sects of magic that the Ministry likes to pretend don't exist. What exactly do you have to offer, Mr...?”

“Potter. Harry Potter,” Harry said, completely forgetting that he shouldn't be giving his real name to a future serial killer. He fumbled in his pockets, his fingers brushing against something disgustingly slimy. 

That wouldn’t work. 

Instead, his hand locked onto something he had stuffed in his robes right before he got sucked into the book.

He pulled his hand out of his pocket and slapped the object onto the counter with a dramatic flourish.

Tom leaned forward, his dark eyes locking onto the item.

It was a neon-yellow, magically vibrating sticky-note warning label that Harry had torn off the packaging of Tom's own diary. The bright Muggle adhesive paper was literally humming with high-voltage, 21st-century Ministry containment magic, glowing like a radioactive glow-stick in the dim, dusty light of the 1945 antique shop.

Beneath it however, was a small, rectangular metal object.

Tom stared at the neon-yellow square, then at the metal object below it. The sheer confusion on his face was a work of art.

“What,” Tom said slowly, his polite customer-service voice completely evaporating, “is that.”

 “That is the most evil piece of metal you would ever see in your life, young man.” Harry laughed internally after calling Tom a young man.

Tom was silent, waiting for Harry to explain. “It can talk to you.”

***

Tom stared at the small, sleek rectangle of glass and metal. In 1945, Muggles were still using clunky, vacuum-tube radios and massive rotary telephones.

A modern smartphone with a neon Ministry warning label stuck to the back looked like a piece of alien technology. 

Tom stepped out of the counter, now fully interested in Harry’s iPhone 17.

“What does it do? Is it a dark spiritual talisman?” he asked. He didn’t touch it, his fingers hovered over the glass screen, as if afraid it would curse him.

Now it was Harry’s turn to flash Tom a little smile. He tapped on the glass screen, and it lit up the shop immediately.

Thank God Ministry magic has ways to make my phone fully functional without WiFi…

“Watch this.”

Tom inched closer, very, very excited.

“Hey Siri, how’s it going? Write a paragraph on the History of Shakespeare.” He asked.

“Sure! Here is a paragraph on the History of Shakespeare. William Shakespeare (1564–1616) was an English playwright, poet, and actor who is widely regarded as the greatest writer in the English language. Born in Stratford-upon-Avon, he moved to London in the late 1580s, quickly establishing himself as a successful playwright and shareholder in the acting company known as the Lord Chamberlain's Men (later the King's Men). Over a career spanning roughly…” the mechanical, toneless female voice recited.

Tom’s eyes widened. This was an ominous ritual!

“Who is the woman trapped in the evil box?” he asked. “How does she know so much?”

Harry paused. This was going to be fun.

“She is the Woman of Knowledge. She is enslaved in the metal box to help us, and she holds all the knowledge in the world. Her power is not to be underestimated.” He spoke, hoping he sounded scary.

“This feels so… wrong, Mr Potter.” Poor Tom Riddle was absolutely shell-shocked from an iPhone 17.

"Oh, it's very wrong," Harry agreed cheerfully, leaning his elbows on the counter. "It’s a dark artifact of supreme mental destruction. It consumes souls, Tom. People stare into this glowing box for fourteen hours a day until their brains turn to absolute mush and they lose all desire to perceive reality."

Technically, Harry wasn't lying. Screen time addiction was a serious epidemic in the 21st century.

Tom leaned closer, completely captivated. A dark artifact that could effortlessly enslave the minds of the masses sounded exactly like the kind of absolute power he was looking for. He reached out a long, pale finger, gingerly poking the edge of the metal casing.

"How do you activate it?" Tom murmured, his customer-service persona completely dead and buried. His inner Dark Lord was practically drooling. "What is the incantation?"

"No incantation," Harry smirked, thoroughly enjoying how easy it was to play the future Dark Lord like a fiddle. "You just tap the screen. But unfortunately,you need to feed it every few hours. It needs a special kind of... electrical lightning charm to wake up. Quite rare back in Syonan-to, you see."

Tom's brow furrowed. "Electrical? Like Muggle currents?"

"Exactly," Harry nodded. "But hey, if you answer a few of my questions, it’s yours for a cheap price, and I'll teach you how to use Duolingo.”

Tom paused. He was unwilling to answer questions, especially if it was about himself. He regarded the eccentric Mr Potter with growing suspicion, thinking back on their earlier conversation before finally whipping out his wand.

Why is he so aggressive? All I wanted was to promote Duolingo!

“How do you know my name?” Tom snarled, all traces of calm leaving him in a single, terrifying instant. 

The air in the dusty shop turned ice-cold as Tom slashed his wand through the air. A jet of dark, violet light erupted from the wood, aimed straight at Harry’s chest. It was a vicious, silent binding curse meant to pin Harry to the floor.

But Harry hadn’t spent years hunting dark wizards just to get taken down by a nineteen-year-old on a Tuesday.

With the casual, muscle-memory laziness of an overworked civil servant, Harry flicked his own wand out of his holster. He didn't even stand up straight. With a simple, non-verbal Protego, a shimmering silver shield snapped into existence over the glass counter. Tom's curse hit the barrier and ricocheted violently into a shelf of shriveled heads, sending glass eyeballs raining down onto the floorboards.

He was asking for a raise as soon as he got out of here.

Before Tom could even register the shield, Harry twisted his wrist, casting a silent, overpowering Disarming Charm.

Expelliarmus!

The scarlet light flashed across the dim room. The sheer force of the spell tore the yew wand clean out of Tom’s grip. It flew across the shop, clattering uselessly into a dark corner behind an antique wardrobe.

Tom froze, his hand remaining empty in the air, his chest heaving with sheer shock.

He didn't even use an incantation.

Tom’s mind raced, a cold, venomous panic clawing at his throat. He stared at Harry Potter, who was currently brushing a stray bit of dust off his Auror robes as if he had just swatted away a minor housefly.

Nobody disarmed Tom Riddle. Nobody. He was the top of his class at Hogwarts, the heir of Slytherin, a wizard whose magical prowess was decades ahead of his peers. Yet this strange, unbothered man from Syonan-to had stripped him of his wand with a casual flick of his wrist, without uttering a single syllable.

Who is he? Tom thought, his dark eyes narrowing as he frantically evaluated the threat. An assassin sent by Grindelwald's forces? A foreign operative tracking dark artifacts?

More importantly, how did this man know his name? Tom had gone by many aliases in the sketchier parts of London, keeping his Muggle father's pathetic surname buried deep. Yet Harry Potter had dropped it so easily, as if they were old acquaintances.

This kid needs an attitude fix… Harry thought, eyeing the very confused yet intrigued Tom Riddle with mild annoyance.

Seriously, he was about to sell him an iPhone! A creation so ahead of his time! Where were his manners or gratitude?

Tom looked from the glowing, metal Siri-box on the counter back up to Harry’s messy hair and taped glasses. The sheer power radiating off the man was suffocating, but his attitude was entirely wrong. He wasn't acting like a deadly assassin. He looked... bored. Like a man who was actively being inconvenienced by a minor delay.

If this Potter character wanted him dead, Tom would already be a corpse on the floorboards. He was being toyed with.

Who was this man? He couldn’t force him to tell him anything, he was currently overpowered, a feeling Tom realised he did not enjoy very much.

Steeling himself, Tom drew himself up to his full height, masking his terror with a layer of lethal, pure arrogance. If magic wouldn't work, he would use words. He would tear this man's secrets out of him, block by block.