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Back at Orsino's court, the Duke orders his band to play a song he heard the night before.
Curio says sorry, but Feste's not here to sing it. He must be over at Olivia's house because he used to work for Olivia's dad when he was alive.
Duke Orsino tells Curio to find Feste, who happens to be roaming around somewhere in the Duke's pad.
Orsino then turns to "Cesario" and gives "him" some friendly advice, man-to-man, about love. Orsino says if "Cesario" ever falls in love, he should think of the Duke, a "true" lover.
Orsino suspects that "Cesario" (Viola) is in love and "Cesario" admits that yes, "he" is in love with someone who looks like the Duke and is about the same age.
Orsino assumes (or pretends to assume) "Cesario's" in love with an older woman, so he tells "Cesario" it's not a good idea for men to marry older women. "Cesario" should marry a sweet young thing because women age fast, which makes them less attractive to their husbands. Women are also not as attractive after they're no longer virgins. (Don't get mad at us. We know Orsino's being awful here.)
Viola's sad response tells us that she worries about aging and becoming less attractive to a potential husband.
Feste enters and sings a song for the Duke about a man who is "slain" by a "cruel maid." Orsino gives Feste some money for his trouble and says it's late – he wants to go to bed.
Feste makes a crack about how moody the Duke's behavior is before telling "Cesario" that Olivia's looking for "him."
Speaking of Olivia, Orsino brags that no woman can resist his romantic ways. Furthermore, no woman is capable of being so in love as the Duke – his love is like the ocean, etc., etc.
"Cesario" disagrees and says that women are just as capable of love as men. "He" tells the story of his "father's daughter" who once loved a man and says that, if "he" were a woman, he'd love the Duke just as much. (Note: "Cesario"/Viola is being cryptic. The audience knows that Viola is her "father's daughter" and that she does, in fact, love the Duke.)
When Orsino asks what happened to the woman, "Cesario" says she pined away in misery while her unrequited love ate away at her insides, like worms.
When Orsino asks if "Cesario's" sister died, "Cesario" cryptically replies that "he" is the only daughter and the only son in "his" father's house. (Note: It's likely that Orsino thinks "Cesario's" sister is dead. It's also possible that Orsino suspects "Cesario" is a woman in disguise. Most directors stage the scene with an ignorant Orsino. But, we've also seen productions where it seems that Orsino knows "Cesario" is not really a boy. The play can go either way.
Orsino gives "Cesario" a jewel to give to Olivia as a token of his love.