In my experience, there are a lot of benefits to attempting to incorporate flashbacks into any RPG which includes long-lived or immortal characters. The benefits, I have found, outweigh some of the problems that flashbacks can introduce.
Formalize
The first step that I use is to formalize the qualities I expect from a flashback. These include but are not limited to duration, assigning roles to other players to handle, the use of handouts or not to guide or frame the scene within a specific context or point in time, and any prohibitions that might be needed.
Buy-in
Once I am clear on what qualities a flashback will have, I pitch that concept to the players and make sure that they are on board with it. For example, some are reluctant to take on the rolls of NPCs in a flashback, and others might not like whatever prohibitions on action might exist for your flashback scenes.
If the group is willing to go for it, the major hurdles have been passed.
Flashback Scenes
This section of the response will break down how I recommend setting up flashbacks, particularly those which span large amounts of time. My experience with this technique began with experiments with Call of Cthulhu and when Vampire was released I continued those experiments with it and Shadowrun. I found this technique particularly useful during linked campaigns set in both the Dark Ages and the modern day, but it got a good workout during a 6-year long, modern day Chronicle as well.
Goal for the Scene
In this sort of scene there is a point which we would prefer to reveal via play and interaction than simple exposition or information dump. Giving context or weight to Intelligence or Skill checks, meeting characters from the past, recognizing an artifact or fragment of speech, being in a place that was familiar to the character but is unfamiliar to the player are a few examples of when flashbacks can be used to good effect and what clear goal they are intended to achieve.
I find the most common flashbacks are ones focused on information from the past of pertinence in the Chronicle's present, and ones focused flashing back to planning out courses of action to complicated situations.
Example:
The player cannot figure out a puzzle but their character should be able to
- A flashback goal is to give the player deeper understanding of the clues so that the puzzle makes more sense rather than simply rolling Intelligence + Enigmas and getting the answer from the Storyteller.
Goals should be very specific, should allow the scene to be short, and should be clear to the player before they start. They should generally begin with a signal that alerts the player that the current scene is being replaced with a flashback, but sometimes a surprise flashback can have value, too.
Example:
As you take in the images in the mosaic on the floor a memory arises from long ago. You have seen these images before and know what they meant to the people who were inspired to include them in their art... [follow with a frame for the scene].
Goal: understand the meanings of the symbols on the floor to assist in solving a puzzle related to them in the main scene.
Frame for the scene:
Just like any other scene, a flashback should be framed so that the player can get their bearings. Who was there, what was happening, when did it occur originally, where did it occur, why were they in that place at that time, how does that situation inform 'proper' behavior (a revolution is in progress, peasants are starving, the Prince was recently assassinated, etc).
Skill Use and Actions:
Once in the flashback, the player or players are operating within an undefined moment in time within defined moments in time. While in the flashback, they are there as explorers of what happened rather than as agents of change.
We are answering questions of 'what is something or someone like?', or 'how did we learn about this secret passage behind the throne?', or 'what did the Prince whisper to his Seneschal the night he was assassinated?'
We are not giving opportunities to change present day events by acting freely in the past. This is memory, not time travel.
The players are primarily responsible for handling their behavior, but the Storyteller must be willing to step in to keep the flashback on point if their initial framing of the scene is too vague and the players have trouble zeroing in on the goal for the scene.
To keep a flashback from being just a thin veneer over exposition, players should be able to bring some sort of skill to bear or to engage in worthwhile interactions with figures, items, and places from their characters' pasts. To keep this from presenting problems in the Chronicle's present, remembering that the outcomes are already set and that this is memory is important.
- Rolls which risk the sort of failure which could not or did not happen should not be called for.
Example:
The flashback involves two characters locked in combat. The goal of the scene is not to have the fight. The goal of the scene is to 'remember' something about the other combatant. Both characters exist in the present day and it is known that both survived.
Combat checks can still be made in the flashback to bring out the fine details of moments of the action, but these can be interspersed with moments of combat which are purely narrated, and the conclusion of the fight - if it is a part of the flashback at all - will most likely need to be one of those. Skill use during the fight can focus on other things, such as empathy, to help the character's skills and abilities tell that part of the story and make it more than just an information dump.
To make this happen, the Storyteller will need to be willing to skip or gloss over some rolls, call for rolls while the narration of the scene includes the character(s) performing some other action, and carefully framing the purpose of any roll or check so that extreme or poor results do not interfere with the memory being uncovered. In this sort of scene, unlike in a Flashback Planning Scene, failure to complete the scene as framed is not really on the table, (a flashback to a quick conversation with the Prince is not open to suddenly ending in a Frenzy-spawned scene of diablerie).
Flashback Planning Scene:
In some cases a flashback will be not for uncovering a memory of a detail or gaining familiarity with something or someone, but rather it will be for establishing exactly what contingencies were planned for and how those plans were executed. This is, in essence, asynchronous storytelling and when skills and abilities are called into use, failure is very much on the table. The goal is partly to see what was planned for and how it was handled, with failure or success determining modifiers to the real situation in the Chronicle's present.
Example:
The group is creeping into an Elder's Haven to determine if speculation is true and that Elder has fled the city or been destroyed. The Haven is notorious among the city's Vampires for devious traps, secret passages, and confusing layout. Planning for all of these contingencies might be beyond the capacity of the players, might seem both daunting and boring, and/or may drive the players firmly into out-of-character discussion, so running their planning and prediction of problems presented by the Haven can be run asynchronously, as small flashback scenes that deal with each problem as they present themselves in play. This has the added benefit of not using play to time to plan for obstacles which are not encountered in play.
Method:
Run the session as normal up to the point where a problem arises which the characters have a good reason to have planned for, or which a skill check of some kind can justify being prepared for. For example, a character with good skill for investigations might be able to justify having found paper trails which strongly indicate certain things might be in the Haven. This might be determined on the auto as a function of having the skill, or it might be rolled. No further detail needs to be communicated at that time. Fast forward to entering the Haven.
If the session has the characters encounter a large attack dog, a flashback scene can be cued wherein we return to the investigator uncovering records of vet and food bills for the dog which indicate breed and allow them to prepare in advance. Give a time limit for planning and let them go. All skill checks, good or bad, stand and will be used to modify skill checks in the Chronicle's present.
The goal: The goal of this flashback is to give the opportunity to the players to imagine having planned for a problem in advance. They have the problem before them to examine, and can now plan for it directly. They are not being granted automatic success, they are being given the opportunity to earn bonuses, or create penalties for themselves.
