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We had an episode in combat tonight that I was not sure how to adjudicate.
A player character (PC1) with a whip was 10 feet away from an enemy.
In between PC1 and the enemy was another player character (PC2) that was prone.
On the far side of the enemy was a third player character (PC3).
Does PC1 have advantage due to flanking in attacking the enemy with the whip? Why or why not?
If PC2 stands, can PC1 still attack the enemy using the whip, and would this affect advantage in any way?
In particular, the wielder of the whip does not benefit from the optional flanking rules in the Dungeon Master’s Guide.
Flanking on Squares. When a creature and at least one of its allies are adjacent to an enemy and on opposite sides or corners of the enemy’s space, they flank that enemy, and each of them has advantage on melee attack rolls against that enemy.
The wielder of the whip, being 10 feet away from the target is not adjacent, so cannot benefit from the flanking bonus.
There is nothing else in the situation described that would give advantage on the whip attack.
Unless there was any reason why an attack would have advantage, such as if the enemy had been hit by guiding bolt or if P2/3 had taken the Help action, then there's no reason to think that P1 should have advantage due to the positioning of the combantants.
As Thomas Markov's answer points out, the optional flanking rules require you to be adjacent to the enemy to gain advantage, which P1 was not (they were 10 feet away). That said, as a DM, you could rule that reach weapons count as being adjacent for the purposes of flanking if you wish to do so (at least if it's just 10 foot reach, since that could get silly otherwise).
Whether or not someone else is in the way should not, by itself, grant advantage or disadvantage. However, a DM might rule that P2 being "in the way" might grant the enemy an increased AC due to the rules on cover.
The prone P2 would of course create less cover for the enemy than a not-prone P2. Some DMs might rule that a prone P2 grants no cover (which is what I'd rule), whereas others may grant half-cover (+2 AC) to the enemy. Once P2 gets up, some DMs may rule that the enemy has either half- or even three-quarters-cover (+5 AC).
Further reading: Do prone creatures provide cover?
