Troilus Mocking Lovers
This irony occurs early in Book I, and is apparent to both the audience and Troilus. While visiting the Palladium, Troilus mocks love and all those who succumb to it. This is an irony so obvious to the audience, who are already aware of Troilus’ future love affair with Criseyde. Almost as soon as Troilus taunts his knights for staring at women with longing, he is struck by the God of Love, and then becomes enchanted by the sight of Criseyde. Troilus will of course go to extreme lengths later in the story, all in the name of the love he formerly derided.
Criseyde's Betrayal
In the third book, Criseyde delivers an impassioned speech about the poisonous nature of jealousy after hearing of Troilus' suspicions. She derides jealousy as a sign of worldliness and questions if their love is real when it comes with so much insecurity. She encourages Troilus to trust her completely. Although she has wrongly been accused for being unfaithful here, she will ironically end up betraying Troilus later in the story. This betrayal seems especially contradictory in light of her vehement words about fidelity.
Troilus as the Chivalric Hero
The traditional structure for a medieval romance is a chivalric hero courting an innocent maiden. As the protagonist, Troilus automatically inherits this title of chivalric hero. There are some points of the story where he fully embraces this, such as during the parade, when he displays just the right balance of modesty and pride. Yet there are few other instances to suggest he fits this mold. Troilus only desires Criseyde from afar, and completes no brave feat to win her affections; instead, he relies on Pandarus’ tricks to bring them together. Ironically, Troilus seeks to fulfill the image of chivalry to impress his lady, but in private is seen mostly in despair and weakness.
Calchas' Actions
Calchas, the Trojan traitor who has moved to the Greek camp, asks that his daughter is returned to him in exchange for a captured soldier. He proposes this trade with good intentions to be reunited with his daughter, under the assumption that she will be delighted at this news. Yet he has no idea what trouble he is creating for Criseyde and Troilus, who are devastated that they will be separated. This decision is ironic considering that Calchas is said to be a wise soothsayer who can see outcomes before they happen. Another ironic moment comes later when Criseyde's ladies congratulate her on the exchange, thinking she is happy to see her father again, when really she is utterly miserable.
