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1. Check out Women of Letters
The global literary series continues its monthly residency at Joe's Pub. This week's theme: "A Letter To My Greatest Teacher", featuring Katja Blichfelt (the award-winning co-creator/director of High Maintenance), New Yorker contributor Alexis Okeowo, and four other awesome literary ladies. Proceeds from ticket sales always benefit the New York Women's Foundation, so there's really no excuse not to check it out. (Joe's Pub at the Public Theater, 7pm. $20)
2. Listen to Alan Cumming sing sappy songs
The Cabaret star joins long-time Emmy-winning musical director Lance Horne and cellist Eleanor Norton for an evening of classic music in his Café Carlyle debut. The bright-eyed actor will perform songs by Stephen Sondheim, Billy Joel, Miley Cyrus and many more. (Café Carlyle, 35 E 76th St, 8:45pm, $100-$165 plus $75 minimum)
3. Test your TV knowledge at Orange is the New Black Trivia
Revisit all the drama that’s gone down with the women of Litchfield Penitentiary, before the hit Netflix drama returns for a third season this Friday. Big Daddy’s on the Upper East Side is hosting a trivia night tonight with questions about the first two seasons. How well do you know your Crazy Eyes? (Big Daddy’s, 239 Park Ave, 8pm, RSVP at 212-717-2020. Free.)