Illusory Script

Inform, improve, and inspire your game.

  • Home
  • Archive
  • Publications
  • Contact
  • About
  • Subscribe

Flanking Makes 5e Less Interesting

by Marius on April 27, 2024
Art generated by playground.ai using the prompt, "two-dd-characters-flanking-a-monster-in-a-battle-in-a-fantasy-swamp-mysterious"

Flanking is an optional rule. It says that if characters are in melee with the same creature and on opposite sides of the target, the characters have advantage on melee attacks. Many tables seem to use the rule but I don’t. There are two main aspects which make flanking a rule which makes the game less not more interesting:

  • Flanking makes advantage from other sources worthless.
  • Flanking doesn’t incentivize interesting positioning.

In addition, there’s an alternative to flanking which can make combats more dynamic and cinematic.

Flanking and other sources of advantage

Why even cast faerie fire when you can flank? Why hide for sneak attack? Flanking is the easiest way to get advantage. No roll necessary, just stand on opposite sides of the target. Without flanking getting advantage becomes a significant goal for any combat. Players look for opportunities to gain or grant advantage. And we DMs can offer advantage situationally. The enemy was grappled with a natural 20 on the grapple check? Perhaps the next attack has advantage against it. If the melee characters have advantage anyways, these kinds of situations become meaningless.

Flanking and positioning

Advantage is so good, so impactful that characters will do almost anything to get it. Especially melee martial characters. With flanking, therefore, standing on opposite sides of an enemy becomes the single overriding goal of positioning. Any other considerations don’t really matter. Taking cover, exploring magical monuments, using terrain features… if there’s a simple way to get advantage, that’s the way characters should position.

In my experience, that makes combat less interesting. If I can predict where the melee characters are going every time initiative is rolled, it’s a less interesting game.

Cinematic advantage

Here’s an alternative put forward by Mike Shea from slyflourish.com: cinematic advantage. Basically, characters can gain advantage on attacks for doing something cinematic. An ability check determines whether the character is successful in their cinematic attempt.

For example, a character wants to swing from a chandelier and then land a jumping dagger strike on an enemy. Clearly cinematic. We tell the player that they can attempt a DC 14 Dexterity (Acrobatics) check to gain advantage on their next attack. However, if they fail, the character has disadvantage on the next attack. Clear stakes, a tactical decision, and a cinematic move. While it takes more time than flanking, this version of gaining advantage is more engaging, more cinematic, and therefore more interesting for the game.

Flanking is not the default

Flanking is not the default. And that’s good, I believe. There are more interesting ways to get advantage which flanking negates. We can use flanking in some games. For example, for a combat in tight corridors, we could decide that flanking is actually so effective that we’ll use the rule.

But in my experience, a game is more interesting if flanking is not the default for every session.

Subscribe!

🦹🏼‍♀️ Never miss an article 🪄

... and receive the Illusory Script Ritual Generator!

We don’t spam! Read our privacy policy for more info.

Check your inbox or spam folder to confirm your subscription.

Related Articles

Subscribe!

🦹🏼‍♀️ Never miss an article 🪄

...and receive the IllusoryScript Ritual Generator!

We don’t spam! Read our privacy policy for more info.

Check your inbox or spam folder to confirm your subscription.

Latest Articles

  • D&D 2024 Player’s Handbook ChangesApril 26, 2025
    The D&D 2024 revision of the Dungeons & Dragons Player’s Handbook brings a host of small mechanical changes to the game. If you’re a Dungeon Master already familiar with the 2014 ruleset, here’s a focused guide to what has changed—and how it might impact the way we run our tables. Rather than being a full …

    Read On »

  • Make a City Come to Life in Any RPGApril 19, 2025
    Preparing Urban Chaos for the Table A city can breathe fresh life into any fantasy RPG. They’re where intrigues are born, gold changes hands, and alliances get sealed or shattered over a drink. But when we GMs need to prepare one, especially for just a session or two, cities can feel like an overwhelming tangle …

    Read On »

  • Tracking Damage to Monster GroupsApril 5, 2025
    Hit Points Are a Lie (and That’s Okay) In a previous article about the Encounter Damage Tally, we explored a clever way for tracking monster damage: rather than counting down hit points for each individual monster, we tally up the total damage dealt in the encounter. When the tally reaches a monster’s average HP, we …

    Read On »

  • 10 One-Shot Outlines for Your Next Game NightMarch 29, 2025
    Running effective D&D one-shots can feel daunting – we DMs must deliver a complete adventure within a tight timeframe. With only three hours to play, clarity and structure are essential. And that’s where the following one-shot outlines come in. In my experience, in three hours we can realistically run three distinct scenes. Plus a mini …

    Read On »

  • Custom Backgrounds for Campaign Buy-In (D&D 5e 2024)March 22, 2025
    Custom Backgrounds for Campaign Buy-In Session Zero our chance to tie characters to the campaign’s world from the start—and one of the strongest tools we have is often overlooked: custom backgrounds. Used well, custom backgrounds act as anchor points. They ground characters in the setting, hint at future plot threads, and give players a starting …

    Read On »

  • NPC GeneratorMarch 15, 2025
    Sometimes you need a quick NPC. Someone for the characters to interact with in a scene. The NPC should have some unique features, a personality, and something to help the DM roleplay the NPC. That’s what the Illusory Script NPC Generator is about. We have written previously about NPCs, and this generator is built on …

    Read On »

...browse all articles...

Subscribe!

🦹🏼‍♀️ Never miss an article 🪄

...and receive the IllusoryScript Ritual Generator!

We don’t spam! Read our privacy policy for more info.

Check your inbox or spam folder to confirm your subscription.

  • Privacy Policy
  • Impressum
  • Marius’s House Rules
© 2025 Illusory Script.
✕
  • Home
  • Archive
  • Publications
  • Contact
  • About
  • Subscribe