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I have a player who, after giving their consent, is playing an undead character with amnesia that only I, as the DM, know the backstory of. In life, this character was famous and has mysteriously disappeared. Upon hearing that a famous person mysteriously disappeared, the player wishes to cast sending to see if the missing person is still alive.

  1. Is a character considered familiar with themselves if they have amnesia?
  2. Assuming they are, would they basically just hear an echo in their head of the message they just sent?
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Regarding familiarity

Familiarity is not a very precisely defined rules term, so interpretation of it really falls back to precedent, interpretation, and DM rulings. In terms of precedent, the most precise definition of familiarity comes from the Teleport spell:

“Very familiar” is a place you have been very often, a place you have carefully studied, or a place you can see when you cast the spell.

Assuming that "Familiar" is similar but less restrictive than "Very Familiar", then we have some suggestions for how to determine familiarity. As a DM I would rule that without the knowledge "Person A and Person B are the same Person" then "met Person A often" or "can see Person A as you cast" wouldn't be sufficient to say you're familiar with Person B and sending would fail. I don't think other interpretations are necessarily invalid, but the idea of using Sending with someone really specific as the recipient "Just in case I've met them before and just didn't realize it" seems very against the spirit of the spell and also a huge DM headache.

The other method, "studied carefully", could indicate a method to become familiar through indirect learning, but Teleport helpfully provides other "levels" of familiarity, such as:

“Description” is a place whose location and appearance you know through someone else’s description, perhaps from a map.

which is the lowest level of familiarity, only one step above trying to teleport to a place that doesn't exist. The fact that it's on a chart as a level of familiarity at all could mean it qualifies for "familiar", but I would say Teleport's precedent indicates that you can't cast Sending from just a description.

Regarding self-targeting

As for what would happen if someone did manage to Sending them-self, in general the caster of a spell is only an invalid target if the spell's description directly prevents it, either with a special exception (e.g. "a creature other than the caster") or by general rule that includes the caster (e.g. "an enemy"). Sending only provides the "Familiar" restriction, so if the Caster is familiar with themselves (as discussed in the first paragraph) they should be a valid option to receive the message. As for what the result would be, the SRD entry for Sending states:

The creature hears the message in its mind, recognizes you as the sender if it knows you, and can answer in a like manner immediately.

So I think it's clear that the caster would indeed hear the message again in their mind, and they would be entirely certain that it was due to that Sending being sent to themselves (and would then have the option to give a response, though I doubt there would be a reason to). The spell description does not provide any evidence that a failed Sending would be in any way similar to a successful Sending to yourself, nor does it provide any means by which insufficient familiarity would result in the message being sent to the wrong creature, so I think it would be pretty unambiguous that the caster and the intended recipient are the same person.

TL;DR

The Sending to a missing person should fail due to unfamiliarity. How much the caster should know about why it failed is somewhat ambiguous so a DM can rule either way, but the most common interpretation seems to be that the caster wouldn't be able to tell the difference between a Sending that succeeded but received no reply, a Sending that failed due to unfamiliarity, and a Sending that failed due to the 5% failure in cross-plane casts.

I'm fairly confident in my understanding of Sending, though a DM is allowed to change that. For example, if the later dramatic reveal is REALLY IMPORTANT then just deciding that Sending cannot be sent to the caster seems reasonable, as long as that's applied consistently and you don't just make up new reasons out of nowhere why other people can't do the sending or whatever. On the other hand, my definition of Familiar is an interpretation based on precedent and it's reasonable to rule otherwise if you do want this to be possible.

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    \$\begingroup\$ I thought in general a caster who fails to cast a spell doesn't always learn exactly why the casting failed. But I'm not sure if anything in RAW addresses this. \$\endgroup\$ – aschepler Feb 14 '18 at 13:05
  • \$\begingroup\$ @aschepler That's a good point, I'll update with some more details about that. \$\endgroup\$ – Kamil Drakari Feb 14 '18 at 15:42
  • \$\begingroup\$ This approach to familiarity does open the door to the character being able to research the famous individual. Perhaps finding and talking to someone who knew him personally would help; maybe there is a portrait in a noble's private collection... Lots of possible adventure hooks, and allows the sending to work when it suits the story. \$\endgroup\$ – richardb Feb 14 '18 at 18:38
  • \$\begingroup\$ I find it easiest to reason via: Would knowing Clark Kent let you Sending Superman (which you've only heard of)? I'd say no. I can see this being used for all sorts of shenanigans otherwise. \$\endgroup\$ – TemporalWolf Feb 14 '18 at 23:59
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You are deep into Homebrew and DM fiat territory.

You have a player playing a character for which the rules were not designed, so we must take what we know of the spell and see what we can make work.

You send a short message...to a creature with which you are familiar

Familiar is an ill-defined term. Can you be familiar with someone you have never met? Unlikely, but a broad interpretation of the word might allow you to target someone you have seen and heard many times. A peasant might not know their king personally, but may have heard him speak and seen him on parade often enough for a DM to say this is familiar.

It is unlikely that someone only known through hearsay or rumor could be considered familiar by any stretch of the imagination, otherwise the restriction would really have no purpose in the spell.

So it comes down to : Is the amnesiac character "familiar" with their previously living self? Since there are no specific rules detailing this unique homebrew relationship, it comes down to, as I said, DM fiat. The DM must adjudicate this with an eye toward fairness, whether success serves the story or the character arc, and whether it is fun.

If the intent of the character was a voyage of self-discovery, then this might be a triggering event in that character's career. If the intent behind the character is a "lifetime" of anguish and uncertainty, then the DM could judge the familiarity standard is not met, or is only partially met with a cryptic result.

Ultimately, since the rules won't serve, this becomes the job of the DM, and would certainly vary from table to table.

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    \$\begingroup\$ One important question this touches on, but doesn't say explicitly: Does her finding out that they used to be this famous person serve the narrative? Is now a good time for them to start confirming their past, or would that be better served later? \$\endgroup\$ – Ifusaso Feb 13 '18 at 16:46
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    \$\begingroup\$ I agree. The PC is familiar with the persona or reputation of the famous person, but not familiar with the actual person. \$\endgroup\$ – MivaScott Feb 13 '18 at 18:11
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    \$\begingroup\$ @Ifusaso I do question if it "success serves the story ", which is probably close enough. \$\endgroup\$ – keithcurtis Feb 13 '18 at 18:42
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    \$\begingroup\$ There's a middle-ground, if you want to turn your PC paranoid; have Sending "seem to do nothing" then shortly afterwards they hear whispers and echoes in their head which start getting louder to the point of being painful, like a feedback loop. You have some scope for creative handwaving here, since RAW doesn't really give you a hard answer \$\endgroup\$ – Joe Feb 14 '18 at 11:04
  • \$\begingroup\$ When everyone in the realm can cast Sending to tell the king what they think about his government policies (and the king wouldn't know who it is because they don't know all their subjects personally) then I really pity him. \$\endgroup\$ – Philipp Feb 14 '18 at 16:42
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Using the spell description creatively

From a reading of how the spell works, one creature sends a message to another creature, but it does not specify that it cannot be the same creature.

You send a short message of twenty-five words or less to a creature with which you are familiar. The creature hears the message in its mind, recognizes you as the sender if it knows you, and can answer in a like manner immediately.

Since the spell doesn't clearly address "sending a message to yourself" there is room for a ruling.

  1. If the message arrives instantaneously, there would be no echo. The message would be heard simultaneously with sending it, so the sender most likely will not notice it being received at the same time. (Credit to @ChristofferHammarström).
    Insofar as a ruling on whether or not the character notices something odd, an Arcana or Insight check would be appropriate, but perhaps at disadvantage due to not knowing why and the odd circumstances based on your adventure's story.

  2. For a more humorous ruling, every time they try to cast sending they just get a busy signal. "The Wizard you are trying to reach is currently in another call, please try again later." click (credit to @Malco).
    This approach gives a clue that the spell isn't working as usual, and may lead the player to puzzle out what is going on, and in turn solve the mystery. Depending upon how much using this to solve the mystery might upset your story or adventure will guide you in whether or not to use this description of what happens.

  3. Using this as a clue that "something strange is going on here," the character will hear the message in the form of 'voices in my head' that now and again crops up in dreams. Your character has a split personality, and the subconscious can do strange things. Using the dreams as the linkage here is the something buried deep in the brain of the character, before it was transformed, getting a message ... but from where?
    This can provide a clue on solving the mystery, depending on how the player puzzles this all together.

  4. Taking the problem to be solved at face value: you have an undead character with amnesia and the player wishes to cast sending to see if the missing person is still alive. Since the character is undead, the person is not alive. (Technically, undead are reanimated). With that ruling, he should not get an answer, since the person he is looking for is no longer alive: the intended recipient of the message is deceased. (credit @Trish)

    Undead are once living creatures brought to a horrifying state of undeath through the practice of necromantic magic or some unholy curse. Undead include walking corpses, such as vampires and zombies, as well as bodiless spirits, such as ghosts and specters. (DM, Basic Rules, p. 2)

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