Jessica, daughter of Shylock, sings of the end of love. Her marriage to Lorenzo is on the rocks. She is friends with Lancelot, her father's former servant. She pretends to be a boy to become a student of her father's in Judaism and finance. Doña Gracia, great lady of the Jewish world, vets hilarious suitors for herself and her daughter Ana.

Meanwhile, Gracia's jealous (and evil) sister Brianda conspires with Portia to sic the Inquisition on Gracia and Jessica. When Jessica (as Jonathan) begs Gracia to keep Shylock from the baptismal font, she can't do it, but Ana shows up and falls in love with "him." A comic balcony scene ensues when "Jonathan" stays overnight at Gracia's palace. Ana, not to be deterred, follows "Jonathan" and catches up with "him" in the forest. Jessica reveals herself in an extraordinary love scene and the two women end up spending the night together, guarded by a hidden Lancelot.

Brianda seduces Lorenzo, Malventio (a very important Inquisitor), and her own lawyer, setting them against each other while she collects her half of the family fortune and escapes Venice.

Lorenzo gets an annulment and denounces Jessica, who is arrested. Lancelot pleads with Gracia to help her and this happens. He pleads with Shylock, who strongly resists until he learns she is again a loyal Jew, whereupon the contradictions in his mind cause a stroke. Gracia saves Jessica, who embarks on a voyage to the new world, where she finds redemptive love and marries again, this time a Jewish doctor in Brazil.

Lancelot (also married, to a very smart Christian-Moorish woman who has his baby on the boat), sings the epilog, "All's right with the world." But a cutpurse, a junior Inquisitor, an Indian servant, and an African slave join in, suggesting future complications.

This play centers on and is driven by four strong women.

SCENE BREAKDOWN & SYNOPSIS

ACT I

SCENE 1: JESSICA sings of lost love. She and LANCELOT banter, having grown up together. LORENZO comes in angry, breaks up the tête-à-tête. LANCELOT invites him alone to a dinner at BASSANIO and PORTIA’s. He goes out with the boys.

SCENE 2: LANCELOT makes the same invitation at BRIANDA’s apartment, where ANTONIO spends his life on the couch, but gets excited at the prospect of seeing BASSANIO.

SCENE 3: JESSICA finds the pants she used to wear when hanging out with LORENZO’s friends. She decides she can do more with them.

SCENE 4: In her palace in Ferrara, DOÑA GRACIA vets a suitor, the DUKE OF DANDEE. He doesn’t stand a chance for her or her daughter, although he is the height of fashion.

SCENE 5: JESSICA in pants is outside the gate of the Jewish Ghetto when she realizes it’s the Eve of Atonement. She runs into TUBAL and CHUS on their way to synagogue, and follows them.

ACT II

SCENE 1: FENICIO and BRIANDA discuss how they can get her share of the family fortune despite her sister DOÑA GRACIA’s opposition.

SCENE 2: GRACIA vets another suitor, the PRINCE OF PALTRIE, obsessed with numbers (especially monetary), and only interested in her. As with the DUKE, she makes a fool of him.

SCENE 3: JESSICA in pants visits the home of CHUS, where she becomes an anonymous student of her father SHYLOCK, hiding in the attic there.

SCENE 4: BASSANIO and PORTIA have their dinner party, PORTIA fallin off her high platform shoes. ANTONIO gets really excited about BASSANIO. BRIANDA and PORTIA plot to sic the Inquisition on secret Jews like DOÑA GRACIA and JESSICA.

SCENE 5: At her insistence, JESSICA (in pants) and SHYLOCK study Jewish ideas on forgiveness. It doesn’t go well

SCENE 6: JESSICA and LORENZO discuss their marriage. This also doesn’t go well. JESSICA wants to try again, LORENZO wants an annulment.

ACT III

SCENE 1: JESSICA, as “Jonathan,” visits DOÑA GRACIA in Ferrara. GRACIA finds “his” request to get “his” master SHYLOCK spared from baptism ridiculous, but really likes “the boy.” Daughter ANA shows up and falls in love with “him” at first sight.

SCENE 2: A cloaked ANA shows up under “Jonathan’s” window and throws a rock that hits “him” in the head. JESSICA is pissed, but her main concern is that her new patroness’s daughter is in love with the boy she isn’t.

SCENE 3: GRACIA, more and more impressed with “Jonathan,” tries to convince him to marry ANA. JESSICA ties herself into knots explaining why “he” can’t. (Also: MOSES, SOLOMON)

SCENE 4: Over ANTONIO’s initial jealous objections, BRIANDA and MALVENTIO discuss the Inquisition and how to deploy it against GRACIA, JESSICA, and SHYLOCK.

SCENE 5: ANA in pants catches up with JESSICA in pants in the forest and declares her love for “Jonathan.” JESSICA sees the jig is up and proves she is not male. ANA convinces her they should have a night of love anyway. LANCELOT, in hiding, declares he will protect them.

ACT IV

SCENE 1: DINGLE and his OFFICER come to BRIANDA’S to evict ANTONIO and ridiculously charge and arrest him.

SCENE 2: LORENZO kicks JESSICA out, declaring all her wealth is his. Despite LANCELOT’s attempts to protect her, Inquisition soldiers arrest JESSICA.

SCENE 3: BRIANDA seduces LORENZO, then pretends a letter she gets means MALVENTIO is after him. He flees. MALVENTIO shows up, she extends her seduction of him, and sends him chasing LORENZO.

SCENE 4: LANCELOT tussles with MOSES but gets to see GRACIA, tells her who Jonathan really is, and enlists her to save JESSICA from the Inquisition.

SCENE 5: JESSICA’s soliloquy in prison.
SCENE 6: LANCELOT tells SHYLOCK of JESSICA’s plight. He doesn’t care until he hears she recites “Hear O Israel” to the torturers. He has a seizure/stroke.

ACT V

SCENE 1: JESSICA tells TUBAL she is leaving for Olinda, Brazil, and convinces him to invest in her sugar plantation.

SCENE 2: MALVENTIO enlists FELINUS, a junior Inquisitor, to follow the Jews to Olinda.

SCENE 3: JESSICA disembarks at Olinda. LANCELOT in disguise and a SAILOR carry SHYLOCK off the boat. DR. GOMEZ shows up with HANNAH and her baby, whom he has delivered. She (a Christian Moor) and LANCELOT stowed away. GOMEZ greets his son DAVID, who also greets JESSICA, his possible betrothed. LUPOMENO and FELINUS disembark and argue.

SCENE 4: CALIBOL and SAMSON discuss their fates under the thumbs of white conquerors.

SCENE 5: DAVID tends to a sick FELINUS on the road, who tries to refuse his care because he is Jewish.

SCENE 6: DAVID and JESSICA have a love scene in which they don’t touch, JESSICA being appropriately skeptical about marriage and men. But he is winning her over.

SCENE 7: DAVID tries to follow up on his patient FELINUS at the BISHOP’s, where FELINUS has been chastising the BISHOP for coddling Jews.

SCENE 8: LUPOMENO sings a song about how much he loves picking pockets.

SCENE 9: LANCELOT and his bride HANNAH have a wild lesson (given by her) on the Jewish marriage contract. The wedding procession comes in, as LUPOMENO picks pockets. The RABBI marries JESSICA and DAVID. LANCELOT offers a happy singing epilog, but LUPOMENO, FELINUS, CALIBOL, and SAMSON join in and loom over the dancing.