“Irony is a way of containing two opposites in your head at the same time.”

–Douglas Coupland, “The Post Modern Ironic Wink,” in To the Best of Our Knowledge, Wisconsin Public Radio, Jun 26, 2005. 

“The Socratic personality was ethical precisely because it was neither fully presented nor at one with itself but in a state of constant presentation.  Indeed, contrary to both traditional and modern readings of Socrates, the Romantics also stressed the contradictions of irony and Socratic irony (Albert 1993).  Irony was not just signaling the opposite of what was said; it was the expression of both sides or viewpoints at once in the form of contradiction or paradox: ‘Irony is the form of paradox.  Paradox is everything simultaneously good and great’ (Schlegel 1991, 6).  And any reader who feels that ‘behind’ the irony there is a hidden sense has fallen into the very simplicity and singleness of viewpoint that irony sets out to destroy.  For Schlegel, therefore, the dissimulation of Socrates was not in the service of intending another higher or non-contradictory idea that the privileged few might understand and that might resolve the dialectic; it was about allowing—almost involuntarily—both sides of a tension: 

Socratic irony is the only involuntary and yet completely deliberate dissimulation.  It is equally impossible to feign it or divulge it.  To a person who hasn’t got it, it will remain a riddle even after it is openly confessed.  It is meant to deceive no one except those who consider it a deception and who either take pleasure in the delightful roguery of making fools of the whole world or else become angry when they get an inkling they themselves might be included.  In this sort of irony, everything should be playful and serious, guilelessly open and deeply hidden . . . It contains and arouses a feeling of indissoluble antagonism between the absolute and the relative, between the impossibility and the necessity of complete communication.  It is a very good sign when the harmonious bores are at a loss about how they should react to this continuous self-parody, when they fluctuate endlessly between belief and disbelief until they get dizzy and take what is meant as a joke seriously and what is meant seriously as a joke. (Schlegel 1991, 13).” 

Claire Colebrook, Irony: The New Critical Idiom (London: Routledge, 2004), pp. 53-4. 

“Irony is a disciplinarian feared only by those who do not know it, but cherished by those who do.  He who does not understand irony and has no ear for its whispering lacks eo ipso what might be called the absolute beginning of the personal life.”

–Søren Kierkegaard, The Concept of Irony (1841) 

“…Where the ideas are in action, we have drama; where the agents are in ideation, we have dialectic. 

Obviously, there are elements of ‘dramatic personality’ in dialectic ideation, and elements of dialectic in the mutual influence of dramatic agents in contributing to one another’s ideational development.  You might state all this another way by saying that you cannot have ideas without persons or persons without ideas.  Thus, one might speak of ‘Socratic irony’ as ‘dramatic’ and of ‘dramatic irony’ as ‘Socratic.’ 

Relativism is got by the fragmentation of either drama or dialectic.  That is, if you isolate any one agent in a drama, or any one advocate in a dialogue, and see the whole in terms of his position alone, you have the purely relativistic.  And in relativism there is no irony.  (Indeed, as Cleanth Brooks might say, it is the very absence if irony in relativism that makes it so susceptible to irony.  For relativism sees everything in but one set of terms—and since there are endless other terms in which things could be seen, the irony of the monologue that makes everything in its image would be in this ratio: the greater the absolutism of the statements, the greater the subjectivity and relativity in the position of the agent making the statements.)”

–Kenneth Burke, A Grammar of Motives (Berkeley, CA: University of California Press, 1969), p. 512.