a bad script and outdated humour. how did this movie get made.. and with winona and hilary attached? am I the only one weirded out by a guy in his late 30s befriending a high school student and going to a prom & after-party full of teenagers with her? every character seems cliche and bizarre at the same time. and their wardrobe is terrible, but maybe that's just because it was 2008

Stay Cool is a romantic comedy that has some fun, but doesn't quite know where it’s going. The story involves a writer who returns to his hometown to deliver the commencement address at his former high school, and along the way he visits some old friends, including his former high school crush. The cast features Mark Polish, Winona Ryder, Sean Astin and Hilary Duff. And while they all play some pretty entertaining characters, they don’t always seem like they're in the same film. Still, a lot of it works and it has some interesting things to say about the high school experience and how it affects our lives. Yet while Stay Cool has its moments, it has trouble delivering a satisfying story.