Communicating with the enemy is a field ripe with opportunity for roleplaying scenarios.
In low technology settings you can dispatch messengers, who can then become embroiled in various adventures of their own along the way. Messengers traditionally have a form of diplomatic immunity, in that they are allowed to convey messages between enemies without being the subject of hostile action as an agent of one's enemy. Breaching this immunity can be a serious breach of protocol, signalling the complete breakdown of communication immediately prior to overwhelmingly hostile action. See, for example, the movie 300 or Aragorn's treatment of the Mouth of Sauron in the film version of The Return of the King (though not the original novel - in which Gandalf explicitly respects the immunity).
With magic or at higher tech levels, remote communication becomes possible, allowing one to speak with an enemy without being in physical proximity. This is good for two-way conversations with affably evil enemies, or one-way taunting. A variant is the dropped note, à la The Riddler communicating with Batman. The cool thing about taunting is that it doesn't have to be the villain taunting the hero... it can just as easily be the other way around.
Tàrkin: We 'ave received ze transmission from ze fleeing ship. It... seems to be dahrected to you.
Darth Vader: Read it.
Tàrkin: "Still alahve." And zen... er... 'ow you say... "L.O.L." Ah presume zat means "lots of love".
Darth Vader: How sweet.
Tàrkin: Now 'ow are we supposed to deal with ze Rebels?
Darth Vader: Do not worry, Governor. I have planted a seed of discord within their little Rebellion. Soon we will have the location of their secret base.
Tàrkin: Ah 'ope you know what you are doing.
Darth Vader: Loyalty can be a fickle flame.
Darth Vader: One just needs the right... persuasive arguments to sway those whom friends might least suspect.
Tàrkin: Ah, you are very clever, Lord Vader. Ah 'ave noticed you 'ave no friends.