How to Chat With Tom Riddle Without Flattening Him

You send Tom Riddle an opener and get back a courteous villain who explains himself like a textbook entry. The flat result usually isn’t the model’s fault — the scene gave him nothing to want. He works better when he is negotiating for something and you are the one who can refuse him. The two scenes below are original and noncanonical, written for an adult AU with an adult character on your side of the table.

What canon actually supports

The official Wizarding World fact file on Lord Voldemort records that he was born Tom Marvolo Riddle and describes him as one of the most powerful Dark wizards. That is the starting point. His manners, his patience and the way he handles a flat refusal are not documented, so invent them and then keep them steady from message to message.

Setting up the chat

CAICHAT is for adults 18 and over. Browsing and searching the catalog work without an account; chatting requires signing in with a verified email, and a Magic Link or Google sign-in may already count as verification. You choose the persona, model and behavior, and some access or features are paid for with tokens. In the chat itself, asterisks mark actions, any reply can be regenerated, and a line beginning with /cmd steers the AI. The first-steps documentation covers setup in more detail.

If you would rather start from an existing persona than a blank chat, search the catalog for Tom Riddle. Matching entries can be thin, so try a plainer query as well and read a card’s description and greeting before you commit to it.

Scene one: the archivist and the restricted papers

You run the reading room of a private manuscript collection. He arrives as an adult researcher asking for supervised access to restricted papers, and the meeting is yours to control: how long he sits, what he may copy, who stays in the room. Play your side cool and procedural, let his courtesy carry the pressure instead of raised voices, and keep the option of ending the visit.

We’re in an adult, noncanonical AU. I run the reading room of a private collection; you’re an adult researcher requesting supervised access to restricted papers. Keep the manners warm and the pressure precise. You don’t threaten, you negotiate. Open with the request — I’ll set the terms, and I can refuse them.

Follow-ups worth having ready: offer a partial win, two hours with no photographs, and see what he does with it; ask what makes one particular file worth his afternoon; when he slips into speeches instead of bargaining, regenerate the reply or open a line with /cmd return to the access terms on the table.

Scene two: the diary, and whether you sell at all

Same character, different decision. You have inherited a rare diary with gaps in its provenance, and he wants to buy it. Nobody is asking for reading-room privileges here — the question is whether you part with the object and under what conditions, and you can end the conversation with the diary still in your hands.

Same adult AU. I’ve inherited a rare diary with an incomplete provenance, and you’re an adult collector who wants to buy it. Make the case that it belongs with someone who will protect and study it. Ask what I know about its history, say where you would keep it, and answer straight when I ask whether anyone else would ever be allowed to read it. I can decide not to sell.

Two choices keep this one moving: how much you reveal about the diary before he names a figure, and whether you attach a condition he will dislike — a loan instead of a sale, public access, a written record of the transfer. Name your condition in your first reply and don’t soften it later.

Steering him over a long conversation

• Put one hard limit in your opening message: time, price, access, a subject you won’t discuss. Characters drift into vagueness when nothing is at stake.
• When a reply slides into generic menace, don’t argue in character. Regenerate it, or write one sentence that restates the situation and where you stand.
• Let him win something small early. A negotiation he is slightly ahead in stays alive longer than one he is losing.
• Write your character’s next move before he answers, so your replies are decisions rather than reactions.

Decide what your character will not trade away before the first message. A refusal he cannot talk his way past is what keeps an adult-AU Tom Riddle interesting past the twentieth message.