The Two Gentlemen of Verona, Chicago Shakespeare Theater. If there’s a lesson to be learned from Shakespeare’s problem play, it’s that men are fickle, conniving travelers down the road to romance. But that they’re also occasionally honorable and irresistibly oafish is evident in a production that breezily aspires to be the highbrow date play of the season.

Director Penny Metropulos, on loan from the Oregon Shakespeare Festival, mounts the play with occasional bursts of brilliance, illuminating Shakespeare’s tale of romantic uncertainty by moving the action to the 1920s–a choice pleasingly supported by Deborah Dryden’s excellent costumes, William Bloodgood’s elegant set, and an onstage piano combo. A few images in the first act soar: silky banners imprinted with snippets from a love letter billow from the rafters; smiles are frozen in the flash of a blinding snapshot. But a meandering second act dulls the senses, and overall the show has a syrupy, soft edge that undermines its resilient female leads.

The cast is excellent. Timothy Gregory easily finds desire and sadness in Proteus, the circumspect lothario; as his lover, Kate Fry cross-dresses with a genial spirit that’s palpable. Scott Parkinson, who has the soul of a vaudevillian, is superb as Speed, an Elizabethan clown by way of Brooklyn.

–Erik Piepenburg