I've also liked the idea of 'Engaging' enemies, and have been toying with figuring out how it would work. I think I would allow characters to engage one enemy for each attack they can make during a normal attack action (so martial characters would be able to engage two at level 5, and fighters would eventually be able to engage four creatures at a time at level 20). I wouldn't require any check or penalty to engaging with a creature, but simply have the rule be:
Engaged. Once on your turn, you can choose to Engage in melee combat with a creature within your reach. While you are Engaged with a creature, you keep track of that creature's movements. If it tries to leave your reach, you can use your reaction to make one opportunity attack against it, unless it takes the Disengage action. Even if it uses the Disengage action, you can always try to follow it, although you can move no more than your move speed minus any distance you moved on your previous turn. If the creature ends its turn adjacent to you, you are still Engaged with it.
You can only Engage with one creature at a time. If you have the Extra Attack feature, you can Engage with as many creatures as you can make attacks during a normal attack action. You choose all of them once on your turn.
Normal opportunity attacks wouldn't trigger simply when a creatures leaves your reach, but instead when a creature enters AND leaves your reach on the same turn (such as when a creature is running past you). So in order to keep your foe pinned down, you would have to Engage with it specifically. Additionally, such things as the rogue's sneak attack, flanking bonuses etc. etc. only work while Engaged.
I'm sure there's some holes in this rule, but I think something like it could work.
Engaged. Once on your turn, you can choose to Engage in melee combat with a creature within your reach. While you are Engaged with a creature, you keep track of that creature's movements. If it tries to leave your reach, you can use your reaction to make one opportunity attack against it, unless it takes the Disengage action. Even if it uses the Disengage action, you can always try to follow it, although you can move no more than your move speed minus any distance you moved on your previous turn. If the creature ends its turn adjacent to you, you are still Engaged with it.
You can only Engage with one creature at a time. If you have the Extra Attack feature, you can Engage with as many creatures as you can make attacks during a normal attack action. You choose all of them once on your turn.
Normal opportunity attacks wouldn't trigger simply when a creatures leaves your reach, but instead when a creature enters AND leaves your reach on the same turn (such as when a creature is running past you). So in order to keep your foe pinned down, you would have to Engage with it specifically. Additionally, such things as the rogue's sneak attack, flanking bonuses etc. etc. only work while Engaged.
I'm sure there's some holes in this rule, but I think something like it could work.
Last edited: