“True character is revealed in the choices a human being makes under pressure - the greater the pressure, the deeper the revelation, the truer the choice to the character's essential nature.” - Robert McKee, Story: Style, Structure, Substance, and the Principles of Screenwriting
Choices and Calculations
The core emotional loop of Dungeons and Dragons is the choice and its consequences. To mean anything, these need to be compelling, and the biggest enemy of engaging, compelling choice is the calculation. A calculation occurs when a Dungeon Master presents a player with a decision which may fit all of the other criteria of engaging, interesting, consequential, important choice but can be made entirely on logic or reason, by the player, in the time frame in which they are given to make the choice.
The most common calculation for a subset of players (One-handed martial classes) is the rapier. If you get 5 Strength-based, weapon and shield Fighters together, you’ll get one with a warhammer, one with a flail, one with a morningstar, and two with longswords. Those weapons are functionally identical except for damage type, and even then there is a lot of overlap. The variety allows the players to express something different between their Fighters. However, if you get 5 Dexterity-based, weapon and shield Fighters together, you’ll get five rapiers. Rapiers are the best weapon if a DEX Fighter wants to be effective in combat (ie cause the most impact on the story), and any other choice sacrifices impact for expression.
Expression is not Sub-Optimal
These calculations are incredibly boring. They have only one optimal solution, which is recognisable as optimal to player when they make the decision. Thus the question isn’t “What does this situation tell us about the character?” but rather “Are you willing to sacrifice impact on the game’s mechanics for a chance at expressing your character?” Besides giving a much less interesting answer, it’s an unnecessary question. Instead, the character’s identity should be tied into the mechanics and the narrative of the game.
Tools to Take Away
Asking your DEX-based fighter to choose which of his divorced parents to make proud, by either taking up the his father’s bow, or accepting his mother’s greatsword is bland and boring. At best you’re forcing your player into a decision, at worst you’re punishing your player for desiring a certain character expression. The gameplay and story of your table should lay together in a warm bed, tangled inextricably. In a Role Playing Game, the Role, the Play, and the Game should intertwine into a beautiful trinity, rather than compete for player interest.
If you want to allow your players the ability to say something about their character, it cannot be calculable. You cannot punish them for choosing the wrong answer. Instead you must offer them intangibles, things that can’t be measured by the same scale. You must push their buttons, keep asking “even now” of the things about which they were so sure last time you asked, when the stakes were lower, when there was less on the line.