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I'm blinded and have a health potion in hand that I want to administer to an ally in an adjacent square.

Do I need to succeed at a DC 11 flat check due to the ally being hidden from me? If yes, would I lose the potion if I fail the check?

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You roll the flat check

Hidden includes, among other things,

..must succeed at a DC 11 flat check when targeting you with an attack, spell, or other effect or it fails to affect you. Area effects aren't subject to this flat check.

Effect is a defined term... sort of. Effects are literally everything that happens.

Anything you do in the game has an effect...

So attempting to use a potion on an ally you can't see is subject to Hidden's flat check.

Losing the potion is less clear, but the default is that it is spent

By-the-book, you must have used the potion in order to make the Flat check.

Unless stated otherwise, it's destroyed after activation.

But this is an oddly specific edge case. It might not make much sense to pour an entire potion out in an attempt to find an ally's mouth. This is a prime example of where GM's can apply the core principle of Creating a Narrative

the players take turns describing what their characters attempt to do, while the GM determines the outcome

If it doesn't make sense, GM's can and should rule that what makes more sense happens (particularly, I believe, in cases where it helps the PC's succeed). In this case, it could go either way. Perhaps you poured it into what you thought was a mouth, but was actually a fold in their cloak. Or perhaps you simply failed to find their mouth and had to give up because combat kept moving. If you're out of combat trying to give a potion to an invisible ally, that changes the narrative as well.

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    \$\begingroup\$ I think a GM could reasonably waive the DC 11 Flat Check too; your ally is willing, so they're actively trying to get the potion to their mouth. Since you already know the square (b/c they're just hidden), missing... doesn't make a lot of narrative sense. A GM could maybe tax the reaction of said ally. \$\endgroup\$
    – ESCE
    Mar 24, 2023 at 15:46
  • \$\begingroup\$ That's definitely an option for a homerule or one-off call. But there is also the problem of the ally being up to 8ish feet away from you since spaces are 5ft big, and the action to administer it is supposed to take about 2s. I would actually be more inclined for the potion administerer to spend a second action to 'locate' the ally to avoid the check. Like an extra specialized Seek action. \$\endgroup\$
    – Ifusaso
    Mar 25, 2023 at 3:10
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    \$\begingroup\$ Throw on top of that that characters' heights vary... sometimes greatly, and being engaged in combat means that you're standing differently, potentially distracted and/or have your adrenal glands on overdrive... and the narrative starts fitting better. \$\endgroup\$
    – Ifusaso
    Mar 25, 2023 at 3:12

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