D&D 5E TOTM and flanking
TOTM is "Theater of the Mind" for the puzzled.
Using my Surrounded houserule, it would work the same.
Surrounded: When you end your turn with enemies on opposite sides of you, you become Flanked until the end of your next turn or you there are no longer enemies on opposite sides of you. When Flanked all attacks on you have advantage.
Adjudicating this in TOTM should be about as easy as on a grid. Can they reach the opposite side? If so, they are threatening a flank. Then on the creature's turn they can get of the threat (killing/pushing a creature threatening the flank, taking OAs by moving, etc) or not.
In TOTM, threatening a flank usually happens on purpose. Preventing it requires a defensive line that is anchored at each end; if the line isn't long enough for anchors, the ends are vulnerable to being flanked. So rolling up the line becomes a threat.
Using my Surrounded houserule, it would work the same.
Surrounded: When you end your turn with enemies on opposite sides of you, you become Flanked until the end of your next turn or you there are no longer enemies on opposite sides of you. When Flanked all attacks on you have advantage.
Adjudicating this in TOTM should be about as easy as on a grid. Can they reach the opposite side? If so, they are threatening a flank. Then on the creature's turn they can get of the threat (killing/pushing a creature threatening the flank, taking OAs by moving, etc) or not.
In TOTM, threatening a flank usually happens on purpose. Preventing it requires a defensive line that is anchored at each end; if the line isn't long enough for anchors, the ends are vulnerable to being flanked. So rolling up the line becomes a threat.
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We don’t sweat it. It’s impossible to play a precision tactics game in your head. People have to let go of some of the minutia.
The zones approach is good because while you lose some of the minutia you gain in some movement. I.e. you can melee attack any NPC in the same zone.
The zones approach is good because while you lose some of the minutia you gain in some movement. I.e. you can melee attack any NPC in the same zone.
Brotton Goodfellow
Explorer
I switched to zones when our game went online and I don’t know if I can ever go back. Like Robus said, don’t sweat it. In fact get rid of AoO’s and Disengage, and watch how fast combat becomes.
Oofta
Legend
I don't use TOTM often, and I don't use the flanking rule in 5E but back when I did in previous editions, it went something like the following.
Player: "Can I get into a flanking position without provoking an opportunity attack?"
DM: thinking it over for a moment, makes a yes/no decision based on how they envision on the scene and explains their answer and reasoning.
Swarmkeeper
Hero
We've abandoned optional flanking altogether in our newest campaign.
We've adopted this philosophy to a large extent - which works well for both gridded tactical combat and for TotM, IME:
Replace Flanking with Cinematic Advantage
We've adopted this philosophy to a large extent - which works well for both gridded tactical combat and for TotM, IME:
Replace Flanking with Cinematic Advantage
DND_Reborn
The High Aldwin
When I run an encounter TOTM, my general rule is if two or more creatures "gang up" on another, I'll allow them to sacrifice their bonus actions to grant other allies advantage. If it is a general melee (multiple foes/allies in a general battle), I rule the overall advantages are all negated, and a creature MUST use their action to grant ONE other creature advantage against a common target. 
Bacon Bits
Hero
I guess I don't understand why this is a question. What is it about flanking that suggests it should be handled any differently than everything else in theater of the mind? What's wrong with: The player asks the DM, "Can I get into a flanking position?" and the DM thinks and gives an answer.
