Playing It Cool (2014)

Chris Evans

Me

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

Hedge Funder

Gerry Bednob

Cabbie / Gabriel

L. Peter Callender

Tourist Couple Girl

Ryan Cover

Hot Girl

Kyle Mooney

Other Dude

Sarah Dumont

Cute Girl

Shelly Slocum

Samson's Wife

Matthew Morrison

Matthew Morrison (as Matthew J. Morrison)

Ashley Tisdale

Ashley Tisdale

Beverly D'Angelo

Lyle's Girlfriend (as Beverly D'Angleo)

Brenda Schmid

Blissful Girl

Scott Evans

Blissful Boy

Precious Chong

Serious Girl

Thomas R. Martin

Serious Guy

Tony Cavalero

Charity Waiter

Catero Colbert

Diner Waiter

Kelsey McNamee

Mother

Abby Ryder Fortson

Little Girl (as Abby Ryger Fortson)

Sean Carrigan

Another Guy

Petie Sjogren

Teenage Girl

Lara Everly

Girl Next Door

Jeremy Glazer

New Guy

Fabianne Therese

College Girl

Carl McDowell

Neighbor (as Carl Mcdowell)

Shantel Wislawski

Supermodel

Michael X. Sommers

San Francisco Bystander (as Michael Sommers)

Nicholas Bearde

6 Year Old Me (as Jaeden Lieberher)

Carmina Garay

6 Year Old Girl

Joey Capone

Abrasive Clerk

Kahyun Kim

Korean Woman

Jason S. Kim

Lacey

Shira Scott Astrof

Vivian

Devon Ogden

Sadie

Cathy Tanaka

Hipster Chick

Jaden Alexander

Photographer (uncredited)

Natalie Marie Ames

Beach Bodybuilder (uncredited)

Drew Benda

Tourist (uncredited)

Julie Berlin

Party Guest (uncredited)

Cici Leah Campbell

Medieval English Peasant (uncredited)

Dwight V Coleman

The Groundskeeper (uncredited)

Sandra Daubert

Valentino Woman (uncredited)

Rick L. Dean

Maid of Honor (uncredited)

Theodore John Forsi

Pedestrian (uncredited)

Jon Robert Hall

Bartender (uncredited)

Matt Harding

Diner Cook (uncredited)

Nicky Hawthorne

Cocktail Waitress (uncredited)

Pamela Keith

Wealthy Woman (uncredited)

Nate Komari

Businessman (uncredited)

Charley Lodi

Casual Traveller (uncredited)

Marcus Natividad

Tourist (uncredited)

Sharelle Smith

Runner (uncredited)

Luci Suicide

Priest (uncredited)

Oliver Trevena

The Best Man (uncredited)

James D. Weston II

Tourist (uncredited)