Orsino is an emotional fellow, who can’t bring himself to court Olivia on his own, so he sends a guy pal to do it for him, in the hope that his eloquent friend will be able to woo her with the words he cannot produce. Against his will, he finds himself being drawn to this “man” because of his “feminine attributes,” and when he realizes it’s a woman, promptly transfers his romantic affections from Olivia onto Viola. Most of them were for superficial reasons such as her appearance and a romanticized view of Olivia. He saw her as beautiful, and got lost in the moment and wanted to make the most of it. Orsino leapt at the chance to break through Olivia’s self-imposed seven years of mourning by asking “Sebastian” to visit her on his behalf. He spends a lot of his time pining, but also doing manly things such as horseback riding, playing billiards, going hunting, and suchlike. He spends much of the play dwelling on superficial things, and not seeing what’s going on right in front of him – namely, that his super wonderful friend isn’t a man at all, but is in fact a woman who is falling in love with him! Nor did he expect Olivia to be so fickle as to fall in love with the “man” he sent to court her on his behalf. But once the truth comes out, he hasn’t much trouble adapting, switching his focus in life, and choosing a new future for himself.

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Orsino is a hopeless romantic who is pining after someone just out of reach for most of the story. He’s built up a narrative about this beautiful, perfect creature and become obsessed with her, even though he knows she’s beyond his grasp due to her period of mourning. Rather than go to her himself and risk rejection or humiliation by her unfathomable refusal, he sends someone else to speak words into her ear, present her with gifts, and do his wooing for him. This allows him to remain at a distance and hold onto the perfect idea of her he has in his head. But the closer he gets to her, the more he divides his affections and starts to become fond of Viola, as if he wants to sabotage his own prospective happiness. He just needs to “pine.” He’s theatrical, open with his emotions, and tends toward drama in his bouts of disappointment, but also is somewhat vain and self-assured.