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?

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    \$\begingroup\$ Could you explain why you think the attack might have advantage? \$\endgroup\$ – Thomas Markov Aug 11 '20 at 4:17
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    \$\begingroup\$ Are you using the optional flanking rules? \$\endgroup\$ – PotatoEngineer Aug 11 '20 at 4:23
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    \$\begingroup\$ Yes, this is assuming optional flanking rules (I have edited it to address this). It seems like my question may be redundant with an earlier question, so thanks to everyone for looking at this! \$\endgroup\$ – BprDM Aug 12 '20 at 18:31

There is no reason the whip wielder would make their attack at advantage.

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.

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    \$\begingroup\$ Clearly, reach weapons were not considered in the writing of the optional flanking rule. So while you are correct RAW. I think as the DM you may want to consider the spirit of the rule and award advantage for flanking. \$\endgroup\$ – Sam Lacrumb Aug 11 '20 at 8:40
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    \$\begingroup\$ @SamLacrumb That does not seem clear to me at least at all. \$\endgroup\$ – Cubic Aug 11 '20 at 10:10
  • \$\begingroup\$ 3.5e had flanking activated when two characters flanked an opponent at any melee range. With that experience in mind, and the fact that flanking was added as an afterthought in the DMG rather than as part of the players handbook, Seems pretty self evident to me. But as always it will end up a DM call. \$\endgroup\$ – Sam Lacrumb Aug 11 '20 at 10:19
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    \$\begingroup\$ @SamLacrumb, there are a lot of rules in 3.5 that did not make it into 5e. If you wish to mix and match, that is of course, your call. But this may lead to balance issues and other shenanigans. I'm also not sure why you think "reach weapons were not considered" The PHB was released August 2014, and the DMG four months later in December 2014. There was plenty of time between the two to understand the ramifications. \$\endgroup\$ – MivaScott Aug 11 '20 at 18:26
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    \$\begingroup\$ @ThomasMarkov because it's harder for ranged attacks to get advantage? My tables use flanking and have always allowed reach flanking. Flanking itself causes more issues with regard to triggering advantage I've found :) \$\endgroup\$ – NautArch Aug 11 '20 at 18:56

There's no reason to believe P1 has advantage in this scenario

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).

The positioning of P2 would not interfere with having advantage or disadvantage, but might give the enemy cover

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?

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    \$\begingroup\$ I'm not sure it's silly to allow it even with an optimized reach build. The whole idea is that a creature is harried by two adjacent enemies (in my mind.) \$\endgroup\$ – NautArch Aug 11 '20 at 11:50
  • \$\begingroup\$ I do not mean to imply that a DM shouldn't allow it if they want to, just that they should bear it in mind (if a DM reads this and is only thinking of 10 feet, I don't want longer reach to "sneak up on them") \$\endgroup\$ – NathanS Aug 11 '20 at 11:53
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    \$\begingroup\$ But they could...wait for it...bugbear it in mind? \$\endgroup\$ – NautArch Aug 11 '20 at 11:53

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