On the surface, Guildenstern seems to be the polar opposite of his friend Rosencrantz. Guildenstern is markedly more anxious than Rosencrantz about the strange circumstances in which they find themselves, beginning with his deep concern about the coin-flipping episode. Unlike Rosencrantz, Guildenstern wants desperately to understand their situation, and he tries to reason his way through the incidents that plague them. Guildenstern’s belief that there is a rational explanation for their predicament leads him to sudden bursts of strong emotion as he grows increasingly frustrated by his inability to make sense of the world around him. Guildenstern’s frustration is heightened by what he sees as Rosencrantz’s jovial indifference, and he lashes out at his friend on several occasions. Guildenstern’s angry despair reaches its peak near the end of the play. His realization that he and Rosencrantz are about to die without having understood anything leads him to attack the Player in a fit of fury and hopelessness.

Guildenstern is not simply a blend of rationality and passion. Subtle gestures within the play show him to be capable of compassion and sympathetic understanding. Although Guildenstern is certainly angry at Rosencrantz at numerous points, he quickly consoles and comforts his friend when the need arises. After arriving at Elsinore and becoming even more confused by Claudius’s reception of the pair, Guildenstern soothes a tongue-tied Rosencrantz and promises him that they will be able to return home soon. Similarly, after belittling Rosencrantz for failing to say anything original when they are onboard the ship to England, Guildenstern recognizes his friend’s suffering and promises him that everything will turn out okay. Though he often acts as if he would rather be alone than be with Rosencrantz, Guildenstern’s final speech in the play has him alone onstage, turning to look for his friend, unable to tell which one of them is which.