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Does a Drunken Master Monk have to attack with one of their flurry of blows attacks to activate the disengage benefit?

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No. The benefits of an ability are not its costs/requirements.

Drunken Technique states:

At 3rd level, whenever you use Flurry of Blows, you gain the benefit of the Disengage action, and your walking speed increases by 10 feet until the end of the current turn.

So all you have to do is use Flurry of Blows. The rule for Flurry of Blows states:

Flurry of Blows

Immediately after you take the Attack action on your turn, you can spend 1 ki point to make two unarmed strikes as a bonus action.

Using Flurry of Blows requires you to spend 1 Ki. It is this payment of Ki that activates Flurry of Blows and grants the benefits of Disengage (and 2 attacks).

Put another way, if you use Step of Wind (which allows you to Dash or Disengage as a bonus action and increases your jump distance), you are not required to jump (or even move, for that matter).

If a DM is not inclined to just let you simply choose not to attack with the 2 attacks granted by Flurry of Blows (which seems like a silly insistence to me), consider this: You are able to attack a location, not just creatures or objects:

  1. Choose a target. Pick a target within your attack's range: a creature, an object, or a location.

That location could be any space, including one where no creature exists, which is functionally identical to not making an attack unless there's some reason you absolutely don't want to make an attack at all (eg, something bad happens if you attack).

But then, if you don't want to attack but still disengage as a bonus action, you could just use that 1 ki towards Step of the Wind instead:

Step of the Wind

You can spend 1 ki point to take the Disengage or Dash action as a bonus action on your turn, and your jump distance is doubled for the turn.

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  • \$\begingroup\$ You, alas, would not, in fact, be out of range of all targets; you would still be in range of yourself (and thus be required to punch yourself in the face twice, if you were subject to said house rule requiring the attacks be made) \$\endgroup\$
    – Please stop being evil
    Commented Jul 31, 2019 at 0:06
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    \$\begingroup\$ @thedarkwanderer: You don't need to attack creatures. You can attack a creature, an object, or simply a location: dndbeyond.com/sources/basic-rules/combat#MakinganAttack \$\endgroup\$
    – V2Blast
    Commented Jul 31, 2019 at 0:46
  • \$\begingroup\$ @V2Blast Sure, but if the idea is to avoid being forced to attack a creature, as the answer presupposes, then running away is not a great idea. \$\endgroup\$
    – Please stop being evil
    Commented Jul 31, 2019 at 1:15
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    \$\begingroup\$ Actually, V2Blast makes an excellent point. You don't even need to bother moving. You can just declare that you're attacking a location where no creature or object exists. The attacks are made, nothing happens. It's functionally equivalent to not making an attack most of the time. \$\endgroup\$
    – Rykara
    Commented Jul 31, 2019 at 1:24
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    \$\begingroup\$ @3C2 I prefer to think of it this way: It's not a case of what the rules mandate, but what they allow. FoB allows the monk to make 2 strikes. If the target dies after 1 strike, there's no requirement that the monk has to hit something with a second strike. By extension, neither strike has to be made. Contrast this with, say, a Barbarian's rage which has requirements that must be met or else the rage ends. \$\endgroup\$
    – Rykara
    Commented Jul 31, 2019 at 2:52
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Yes.

From the description for Drunken Master

Drunken Technique

At 3rd level, you learn how to twist and turn quickly as part of your Flurry of Blows. Whenever you use Flurry of Blows, you gain the benefit of the Disengage action, and your walking speed increases by 10 feet until the end of the current turn.

So you do have to use Flurry of Blows in order to activate the Disengage.

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    \$\begingroup\$ The question is asking about making one of the attacks, not just taking the bonus action. You should probably clarify/expand on that. \$\endgroup\$
    – Someone_Evil ♦
    Commented Jul 30, 2019 at 21:09
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    \$\begingroup\$ If your intent is to say that you can't use Flurry of Blows without actually making the attacks (or at least one attack) that are part of Flurry of Blows, you should state that explicitly, and probably support it with citations. \$\endgroup\$
    – V2Blast
    Commented Jul 31, 2019 at 0:24

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