Yentl secretly is instructed in Talmudic Law by her father, a path that is disallowed to women of the time. When her father dies, Yentl makes the decision to cut her hair, take the name of her dead brother Anshel and disguise herself as a boy so she can enter a yeshiva (Jewish religious school). There she becomes friends with her roommate Avigdor, who is engaged to marry a sweet, gentle, and beautiful woman named Hadass.
Complications arise: One day while many of the men are gone swimming, Yentl realizes she is falling hard for Avigdor and can't act on it without blowing her cover. Then suddenly, Hadass's family breaks off Avigdor's engagement. Avigdor had lied about his brother dying of consumption where in truth his brother had gone insane and committed suicide, and the family feared the sickness might run in the family. Distraught, Avigdor comes up with what he thinks is an excellent idea - as his best friend, Anshel should take his place as the groom, and as a result he won't be cut off from Hadass completely. Yentl balks, but she doesn't want to lose Avigdor (who almost leaves the town in disgrace) and Hadass is a nice enough woman. In the ensuing scenes filled with her terror and a few close calls, she ultimately goes through with the marriage.
Since Hadass is nervous about the arrangement, still attached to Avigdor and and in no more hurry to consummate the marriage than Yentl is, things settle down for a bit. However, when the three of them are together, Yentl watches Avigdor staring longingly at Hadass and starts to realize that he's too deeply attached to her to ever reciprocate what Yentl feels for him. Meanwhile, inspired by Yentl's wit and brains, the innocent Hadass starts to express an interest in academic study, which Yentl, recognizing the thirst, is all too glad to indulge. What she didn't intend was for Hadass to start to love her because of it, and when Hadass starts to come on to her, Yentl realizes she can't keep up the charade. She reveals the truth to Avigdor, who is initially furious, then accepting, and even admits he was hiding some feelings for her too. Avigdor and Hadass get back together and Yentl leaves for America where she might have a chance at pursuing her opportunities more openly.
This film contains examples of:
- All Love Is Unrequited: Both Yentil for Avigdor and Avigdor for Hadass (though she loves him, they're prevented from consummating it).
- And I'm the Queen of Sheba: Avigdor's initial reaction when Yentl reveals her true identity:Avigdor: Now my secret: I'm the Tsar of Russia.
- As the Good Book Says...: Part of how Yentl gets out of consummating her marriage: it's apparently very clear in the Talmud that a woman can't consummate a marriage while she's thinking of another.
- Character Title
- Chick Flick: of the drama variety
- Consummation Counterfeit: Yentl gets trapped into an arranged marriage with a woman who doesn't particularly want to marry "him" either. On their wedding night they play around non-seuxally in their bedroom and Yentl "accidentally" spills some red wine on the bed, which is taken by the others at the wedding night party as proof of consummation.
- Hidden Buxom: Yentl binds herself down in order to pass as a man.
- "I Am Becoming" Song: "No Matter What Happens", "A Piece of Sky"
- I Want My Beloved to Be Happy: Avigdor for Hadass when his engagement to her is broken off by her parents and proposes that Yentl marry her. Yentl for Avigdor when she decides to reveal herself and leave Hadass to him while she leaves for America.
- "I Want" Song: "Where is it Written?"
- Incredibly Long Note: Barbra Streisand's final number (Papa Can You Hear Me/A Piece of Sky); her last note clocks in at over 20 seconds. Babs in general is famous for these.
- The Ingenue: Hadass
- Love Triangle: A slightly unconventional one. As Yentl puts it:He loves her, she loves him, he likes me, I like her, and I've reason to think she likes me.She keeps him, he keeps her, I keep things as they were, it's a perfect arrangement for three!
- It gets more complicated later when Hadass starts to fall in love with Yentl/Anshel.
- Meaningful Echo: There are two: "Nothing's impossible!", first uttered to the titular character by her study partner Avigdor after he asks her/him to marry his ex-fiancee, later uttered by her when Avigdor almost leaves town after she refuses the favor. The other is "God will understand. I'm not so sure about the neighbors," first said by Yentl's father when asked why he is closing the windows if God will understand that his teaching her Talmudic law, which was forbidden to women at the time, is not with ill intent. It is said again by her to Avigdor's ex-fiancee (now her legal wife) in the same context.
- Setting Update: The original play took place in 1873. As per the opening titles, the film is set in 1904 instead.
- Sweet on Polly Oliver: After the heroine reveals her, ahem, "self" to her love interest, he bitches her out for a while, and then reveals the following to her:"I didn't want to touch you. I didn't know why. I thought there was something wrong with me. I loved you... "
- Sweet Polly Oliver: The main character became a man in order to attend a school in Jewish Talmudic Law, which was forbidden for women at the time. It made for some really weird love triangles.
- Translation Convention: English stands in for Yiddish and Russian. Appropriate, since the original story was written in English before being translated back into Yiddish.
- Twelfth Night Adventure: The film was set during a time when women were not to become educated.