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I have a character who sometimes triggers her dare's grit-regaining feature as a side effect of killing an appropriately high-HD hostile creature aware of her position in the heat of combat. It's unclear to me how much grit should be regained in this case; we've been just deciding before each campaign but is one or the other of the options better supported by the rules?

To be clear, the character should either have 1 or 2 points of grit after the kill. Killing a creature in combat gives a point of grit, and in this specific situation killing the creature also satisfies the grit-regaining part of a dare, which gives you grit if you have no grit. The problem is that resolving the grit from the kill first means she might be considered to have grit when the dare resolves, even though she didn't when she made the kill and satisfied the trigger condition. If things are resolved in the other order, with the dare going first, then obviously she ends up with 2 grit.

If things happen simultaneously, there's still the issue that one of the things happening is dependent on the other one not happening. When we do simultaneous stuff it seems like that situation is often tricky. Like if fireball and resist fire go off then you are safe from the fire but if the attack of a summoned fire elemental and antimagic field go off at the same time then you get hit once (using my usual system for simultaneous resolution). Simultaneous stuff in Pathfinder is always tricky, so something delving into that beyond 'it happens simultaneously' would certainly be useful.

The dare in question is:

Run Like Hell (Ex)

While this dare is active, your speed increases by 10 feet, and you retain your Dexterity bonus to your AC while running. You regain 1 grit or panache point the first time you are more than 100 feet away from your closest enemy.

, whose condition is sometimes satisfied by the character killing the last enemy within 100 feet.

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You'll gain 1 Grit.

Simple order of operations shows that:

  1. You attack a creature.
  2. Creature is slain, returning 1 Grit to you.
  3. You no longer qualify for Run Like Hell.
  4. Run Like Hell cannot provide you a Grit.

The creature has to be slain first or else you won't qualify for the Grit return feature of Run Like Hell.

This also goes with the intent of the ability Run Like Hell (just look at the name of the Deed).

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Dares are similar to deeds in that they grant a gunslinger or a swashbuckler extra abilities based on either grit or panache, but unlike deeds, dares become active when a member of these classes runs out of her grit or panache, and become inactive until the character regains grit or panache. A dare grants the character a benefit and makes it easier to regain either grit or panache.

(Emphasis mine.)

Killing a creature gives you grit so, as far as I know, you can't gain the benefits of "Run like hell" while grit is in your pool.

Here's the best way I could come up with to gain two grit by combining killing a creature and that deed:

Start at 105 ft. with exactly enough grit to use "Deadeye" deed to attack their touch AC. As soon as you hit 0 grit you can activate "run like hell", which triggers from being 105 ft. away, giving you 1 grit. Then you kill the target, giving you one more.

Here's a way that would seem like it would gain 2 at first glance but would only gain 1:

You're 50 ft. away from creature 1 and 105 ft. away from creature 2. You have enough grit to spend to touch attack creature 1 killing it, and before it dies you activate "Run like hell". Now you are 105 ft. away from an enemy, but you gained grit and no longer gain the benefits of "Run Like Hell".

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