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Stay Cool

Shoulda. Coulda. Woulda.

4.9

1h 34m

2011

“Shoulda. Coulda. Woulda.”

Synopsis

A successful author is forced to confront an unrequited high school crush when he returns home to deliver a commencement address to graduating seniors. Shasta O'Neil, a sexy high school senior flirts with the visiting author and invites him to the prom.

Director

Michael Polish

Trailer

ComedyRomance

high schoolnarrationromcomspeechpromwriterhometownhigh school sweetheartschool commencementreturn to hometownsecond chance romance

Where to Watch

Data provided by JustWatch

Cast & Crew

Winona Ryder

Winona Ryder

as Scarlet Smith

Mark Polish

Mark Polish

as Henry McCarthy

Sean Astin

Sean Astin

as Big Girl

Hilary Duff

Hilary Duff

as Shasta O'Neil

Josh Holloway

Josh Holloway

as Wino

Jon Cryer

Jon Cryer

as Javier

Chevy Chase

Chevy Chase

as Principal Marshall

Jessica St. Clair

Jessica St. Clair

as Darcy Portola

Frances Conroy

Frances Conroy

as Mrs. Leuchtenberger

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