Playing It Cool

Stuffy

Ioan Gruffudd

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Lyle's Girlfriend

Beverly D'Angelo

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Narrator

Chris Evans

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Her

Michelle Monaghan

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Dick

Patrick Warburton

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Samson

Luke Wilson

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Scott

Topher Grace

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Granddad

Philip Baker Hall

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Lyle

Martin Starr

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Bryan

Anthony Mackie

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Ashley Tisdale

Ashley French

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Mallory

Aubrey Plaza

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College Girl

Fabianne Therese

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Matthew Morrison

Matthew Morrison

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Cabbie / Gabriel

Gerry Bednob

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6 Year Old Me

Jaeden Martell

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Lacey

Mikaela Hoover

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Cute Girl

Sarah Dumont

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Other Dude

Kyle Mooney

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Blissful Boy

Scott Evans

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Blissful Girl

Brenda Schmid

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Sadie

Devon Ogden

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