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If I use my last grit point and activate Run Like Hell, when do I gain grit and deactivate the dare? Specifically:

  • If I activate the dare while within 100 feet of an enemy, and then move so that I am no longer within 100 feet of any enemy, are there any circumstances in which I would not regain grit?
  • If I activate the dare while not within 100 feet of any enemies, do I regain grit and deactivate the ability?
  • What conditions cause an enemy to no longer count as an enemy for the purposes of this dare? If I cause the creature to possess the Helpful attitude, is that enough? If they are dead, is that enough?

I'm asking in the context of a strict RAW game with the following relevant house rules:

  • "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." is replaced by "dares become active when a member of these classes runs out of her grit and panache, and become inactive when the character regains grit or panache, remaining active until then."
  • All further references to "grit or panache" in the relevant sections are replaced by "grit and panache"
  • Wherever the RAW require extension, the GM may choose any extension not contradicting the RAW. These extensions will be consistent within a campaign, to the best of the GM's ability, and can be relied on as rules. These extensions may be developed in advance upon request.

In my experience, GM extension as to a definition of 'enemy' has been desirable with regards to situation 3, above, but there may be also several possible published options for rendering things non-enemy (e.g. Charm Person), in addition to rendering them non-hostile (which has been the extension commonly supplied in practice).

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The text of the dare reads:

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.

While the general rules for how dares trigger read:

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 respective pool, and become inactive until the character regains points of their respective pool. They grant the character a benefit and a new ability to regain or increase the ability to regain either grit or panache.

Which the houserules slightly errata.

With this in mind, we'll answer the specific questions:

If I activate the dare while within 100 feet of an enemy, and then move so that I am no longer within 100 feet of any enemy, are there any circumstances in which I would not regain grit?

There are only two such circumstances. The first is if you had already regained grit via some other means, such as by landing a qualifying critical hit or reducing a qualifying opponent to 0 or fewer hit points. As soon as your grit/panache/luck pool ceased to be empty, your dare ceased to be active.

The second would be if you had somehow lost the requisite class feature by the time you escaped your enemies. For example, if you moved more than 100 feet away from the nearest enemy because you died, you would not regain grit because the petitioner template specifies that you lose all class features you possessed. (If, however, you spent your 1 granted feat as a petitioner on Amateur Gunslinger, you might still qualify, as the Dare gained in place of a feat isn't a feat itself, and the Dare furthermore isn't an 'ability gained through class levels'. This is a bit off-topic and probably contentious, however).

Other than that, no, there isn't, beyond the usual Wish/Miracle/GM fiat/direct divine intervention caveat.

If I activate the dare while not within 100 feet of any enemies, do I regain grit and deactivate the ability?

Yes. In this case, "the first time you are more than 100 feet away from the closest enemy" is when you activate the dare, so you'll regain grit and the dare will deactivate.

What conditions cause an enemy to no longer count as an enemy for the purposes of this dare? If I cause the creature to possess the Helpful attitude, is that enough? If they are dead, is that enough?

Yeah, there's not really anything in the rules on this. The rules are clear that if you are confused all creatures count as your enemy and otherwise you never count yourself as an enemy, but beyond specifying certain cases where people do count as enemies (and the spell Unwitting Ally, which only de-enemifies for the purposes of flanking), the rules are completely open on this point. It seems like creatures are either your ally or your enemy, but even that isn't clear in the rules. There's nothing to do here but get a definition from the DM.

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