Playing It Cool

Chris Evans

Narrator

Michelle Monaghan

Her

Topher Grace

Scott

Aubrey Plaza

Mallory

Luke Wilson

Samson

Martin Starr

Lyle

Anthony Mackie

Bryan

Ioan Gruffudd

Stuffy

Philip Baker Hall

Granddad

Patrick Warburton

Dick

Ashley Tisdale

Ashley Tisdale

Matthew Morrison

Matthew Morrison

Jaeden Martell

6 Year Old Me

Fabianne Therese

College Girl

Gerry Bednob

Cabbie / Gabriel

Beverly D'Angelo

Lyle's Girlfriend

Kyle Mooney

Other Dude

Scott Evans

Blissful Boy

Brenda Schmid

Blissful Girl

Sarah Dumont

Cute Girl

Mikaela Hoover

Lacey

Devon Ogden

Sadie