How to handle a plot twist for a character arc?

Question

One of the characters of our roleplay is an elf with amnesia. His background is that he lost his memory and is looking for someone but doesn't remember who he was. I asked the player for more details but he responded that whatever I do with it is fine. So, my plan is to make the group go to the land of the undead and befriend one of them. Eventually, the group will find out that he is the lost friend that the elf has been looking for.

So I have the questions:

1. For a roleplay standpoint, would it be better to reveal it in a climactic moment/fight or let the party find it on its own?

2. How can I give them clues to find it if the player and character doesn't know anything about the person they are looking for?

Clarifications:

• I have run a few campaigns with the players before and all of them had a light tone, focused on comedy (including this).
• The party agreed to have NPC as temporary companions. This will be the case for the undead as well.
• The undead NPC will also have amnesia to prevent him spoiling the twist right away.

Sorry if some of this doesn't make sense. English isn't my first language.

Answer 1

With this story structure, you need to think about how things got this way. In the past, elf E and undead person U knew each other, but things have happened:

• They've both lost parts of their memories.
• U has died and become undead.

It's probably best if they lost their memories for the same reason, because two different causes of memory loss in a story strains credulity. But that doesn't mean they have to have lost their memories at the same time.

Also, U has died, which isn't a terribly unusual thing, and become undead, which is unusual. You need to decide if the reason for that is connected with the reason for the memory losses.

If some enemy of one or both of E and U is responsible for these events, you need to figure out why they're doing these things (a better reason than "just to be evil" is a good idea), who else they've deprived of their memories, and what else they're doing.

At this point, you have the skeleton of a story, and need to flesh it out with more events and NPCs. Doing that will show you the answers to your immediate questions, and they'll be answers that fit your plot.

Your specific questions don't have specific, unique answers. Likely answers are:

1. It's better to let the party to figure it out themselves. "Dramatic revelations" in films and TV are necessary because those media have limited running times, so answers have to be inserted. It's far more satisfying for players to figure out mysteries themselves. However, they may do this much earlier, or much later, than you expect, and many of the clues you plant will be missed or misinterpreted.

2. The clues that set the party on the trail are due to other parts of the plot, which are connected to the reasons for the amnesia, but not the same as them.

Answer 2

While I agree with the excellent discussion in John Dallman's answer, I’d add a few practical suggestions to get you started with your specific questions, because you will have to give the players some clues for them to work it out.

1. The reveal

You control half of this reunited friendship, since the undead character is an NPC. So you can spring the reveal on them if need be! But if you are going to do that, make sure you’ve given them enough hints that even if they’ve not figured out who this person is by then, it will feel satisfying. You want a reaction of “oh of course! Now it all makes sense!”

2. Clues

A great resource for clues in this circumstance will be looking at fictional tropes around amnesiac characters. Details you decide will help with this: neither of them remember anything about each other, but how complete is the amnesia? Do they remember nothing about themselves or their circumstances before a certain point? Is there a specific hole in their memories around a certain time period? Do they remember absolutely nothing about their personal life at all?

Depending on those answers, and the source of the amnesia, they might sometimes feel things are familiar without knowing how. You could insert a few moments of “I don’t know why, but I think I’ve seen this before” or a conviction of which way to go without explanation. These moments could come through in how you interpret the character’s success on a History roll, or you can make specific rolls to remeber things using Intelligence. If these feelings lead them towards the undead lands in a non-obvious way, all the better. You’ll need the player’s okay for this, of course, and you’ll want to make sure not all of the memories point directly at the undead friend, so it’s not too obvious. But this is a technique I’ve found works really well.

Another question is how they experienced losing their memories. Did it happen instantaneously, or did they lose them slowly over days, months or years? If the latter, then once you get to places the elf and undead person had been before, there could be written notes, drawings, personal belongings or other things they left behind to try and help them remember. The videogame Planescape: Torment is a good example of this technique, and also presents lots of variations on how to recover lost memories. The writings or objects could “unlock” memories, or if the memories are permanently gone, they can have a sadder tone, aa evidence of a former life they’ll never remember. As a bonus, this slow recovery also lets you gauge how much the player likes the directions the recovered memories are going, so you can course correct if it doesn’t fit the idea they have of the character.

Answer 3

Our DM did this in three campaigns using dreams and NPCs

Our first campaign figured a warlock, Pact of the Blade, Hexblade Aasimar whose Player Choice it was to not know who he was, where his parents were, nor where he came from. Yes, it was a bit of an edgelord move, but it worked well because the player (1) was consistent, (2) embraced the unknown and (3) enjoyed the twists and reveals along the way.

How can I give them clues to find it if the player and character doesn't know anything about the person they are looking for?

His dreams. In our campaign, the dreams of each of the PCs informed story arcs that we could pursue or set aside. The key to this was good DM/Player interaction ahead of time, to give the DM time to weave the nuances of our character development into relevant plot arcs (and not just a bunch of side quests). That made buy-in to a given arc very easy for us, as players.

How many clues?

Each of us had a half dozen clues and pointers toward the unknown bits of our back story (or in my case a revenge arc). The puzzle pieces fell together as each character developed.

Also crucial to the success of this approach is for the DM and the players to have a good trust relationship - I feel that I must emphasize this. (It appears that you have that in your group).

Approach

He wove clues into dreams at first, then clues and tips appeared during some encounters (both combat and non-combat), and them some payoff sessions came along that were each focused on that character's arc. He did this with the other three of us and our backstories as well, even though we didn't play the "I have no idea who I am" card. We, as players, embraced this by supporting the other players/PCs during their mini arcs.

NPC interactions contribute heavily to this

In our hexblade's case, the Shadow realm powers made contact with him now and again; there was this mysterious cat who would crop up in dreams or during play only to disappear again. We ran into a cult in the mountains who ended up having clues as to who he had been previously.
The big reveal came around level 10 or 11, in a non-combat encounter, but right after a combat.

It need not take that long in your campaign: in campaign 2, this same "I don't know who my dad is" backstory was resolved quite a few levels before that. It involved a family signet ring as one of the major clues.

Make sure the player is on board with this

As you have that already covered, using NPCs (to include things like that cat our DM used) and dreams can provide clues along the way so that you can hold the reveal until the time is ripe. If the players guess ahead of time, all the better! (That happened in our second campaign).

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The DM has previously posted here (@BenjaminTHall) on some D&D 4e and 5e topics, but I can't seem to find him here using a search. I have to give him a shout out here. He does what you are asking about extremely well; he is an excellent DM whose world building and style keeps us coming back for more. I ended up joining his games based on some conversations we had in GitP; all games have been on-line/VTT given the geographic dispersal of the players.