If I'm a monk that is being grappled by a monster, can my Way of the Open Hand Flurry of Blows effect to push a creature 15ft away from me break that monster's grapple on me?
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You can do it! The Grappled condition does not prevent you from attacking, it only restricts your speed, and can be broken by pushing someone away (third point):
Grappled
A grappled creature’s speed becomes 0, and it can't benefit from any bonus to its speed.
The condition ends if the grappler is incapacitated (see the condition).
The condition also ends if an effect removes the grappled creature from the reach of the grappler or grappling effect, such as when a creature is hurled away by the thunderwave spell.
Since you can use Attack, you can use the Open Hand Technique, the second effect of which will satisfy one of the conditions to end the grapple:
Open Hand Technique
Whenever you hit a creature with one of the attacks granted by your Flurry of Blows, you can impose one of the following effects on that target:
(skipping the other effects...)
- It must make a Strength saving throw. If it fails, you can push it up to 15 feet away from you.
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2\$\begingroup\$ I think the phrase in question with this rule is "The condition also ends if an effect removes the grappled creature from the reach of the grappler or grappling effect". Stating that the grappled creature, and not necessarily the grappler have to be moved. \$\endgroup\$ Commented Oct 27, 2016 at 13:34
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11\$\begingroup\$ @Pyrotechnical that is actually incorrect. the 'Grappled' condition does not also apply the 'restrained' condition. Certain creatures have attacks (like the Roper) that cause BOTH Grappled and Restrained conditions at the same time; but Grappling a creature doesn't automatically apply the Restrained condition. \$\endgroup\$– AiratomeCommented Oct 27, 2016 at 14:37
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2\$\begingroup\$ @Pyrotechnical the mental image I use to keep that straight is that of having a firm grasp on the off-hand-wrist of a person with an axe. I may have stopped them from going anywhere, but I haven't made murdering me any harder! \$\endgroup\$– nitsua60Commented Oct 27, 2016 at 14:46
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4\$\begingroup\$ @lordoftime I don't read that phrase as requiring that the grapplee must be the one moved, just that they must end up outside the grappler's reach. Which could be accomplished by forcibly moving either the grappler or grapplee. \$\endgroup\$– nitsua60Commented Oct 27, 2016 at 14:47
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1\$\begingroup\$ @Airatome So it is! I think I got so used to getting grappled by things that grab me and automatically restrain that I assumed the two were one and the same. Good to know, thank you! \$\endgroup\$ Commented Oct 27, 2016 at 14:58