Een jongeman (Chris Evans) is gedesillusioneerd door de liefde voor een adembenemende jonge vrouw. Op een benefietdiner besluit hij zich voor te doen als een filantroop om met haar in contact te komen. Ze blijkt echter verloofd te zijn met iemand die niet graag heeft dat ze op een date gaat. Aangemoedigd door zijn eclectische vrienden besluit hij de uitdaging aan te gaan. Hij veinst een platonische relatie met haar om haar te kunnen blijven zien en uiteindelijk haar hart te veroveren.
Nee, helaas is Playing It Cool nog niet beschikbaar op Netflix in Nederland.
| Writing | Paul Vicknair | Screenplay |
| Directing | Justin Reardon | Director |
| Writing | Chris Shafer | Screenplay |
| Production | Chris Evans | Executive Producer |
| Camera | Jeff Cutter | Director of Photography |
| Art | Douglas Woods | Set Dresser |
| Art | Yoel Ancieta | Set Dresser |
| Art | Greg Manke | Props |
| Camera | Brenden "Snake" Craighill | Grip |
| Costume & Make-Up | Adrienne Greshock | Key Costumer |
| Production | Corrie Rothbart | Co-Producer |
| Costume & Make-Up | Beth Pasternak | Costume Designer |
| Sound | Tim Song Jones | Boom Operator |
| Crew | Larry Ferguson Jr. | Post Production Supervisor |
| Art | Gregory R. Wolf | Property Master |
| Production | Jon Poll | Co-Executive Producer |
| Art | Lisa Clark | Set Decoration |
| Art | Michelle Waring | Art Department Assistant |
| Lighting | Luke Kalarickal | Assistant Chief Lighting Technician |
| Costume & Make-Up | Charlotte Parker | Hair Department Head |
| Directing | Rod Smith | First Assistant Director |
| Crew | Kelley Cribben | Post Production Supervisor |
| Art | Myles Lumb | Set Dresser |
| Camera | Timothy Roarke | Camera Operator |
| Camera | William Buckingham III | Key Grip |
| Art | Patrick Lumb | Production Design |
| Crew | Andy Cheng | Stunt Coordinator |
| Camera | Gavin Ames | Steadicam Operator |
| Camera | Michael Orr | Dolly Grip |
| Costume & Make-Up | Unchin Lee | Set Costumer |
| Costume & Make-Up | Deborah Rutherford | Makeup Department Head |
| Production | Paul Vicknair | Co-Producer |
| Production | Bruce Wayne Gillies | Line Producer |
| Art | Patrick Lumb | Set Dresser |
| Camera | John Waldo | First Assistant Camera |
| Lighting | Wadsworth Peters | Electrician |
| Costume & Make-Up | Steve Constancio | Set Costumer |
| Sound | Gabe Hilfer | Music Supervisor |
| Production | Jennifer Haire | Production Supervisor |
| Art | Justin Reardon | Storyboard Artist |
| Production | Kim Davis-Wagner | Casting |
| Sound | Kevin J. Edelman | Music Supervisor |
| Sound | Aaron Levy | Sound Designer |
| Camera | Daniel C. McFadden | Still Photographer |
| Sound | Pawel Wdowczak | Sound Mixer |
| Lighting | Bobby Wotherspoon | Chief Lighting Technician |
| Costume & Make-Up | Debbie Travis | Key Costumer |
| Directing | Jasmine Marie Alhambra | Second Assistant Director |
| Production | Nicolas Chartier | Executive Producer |
| Production | Justine Arteta | Casting |
| Production | Bruce Wayne Gillies | Unit Production Manager |
| Production | Chris Shafer | Co-Producer |
| Editing | Lara Khachooni | Additional Editor |
| Camera | Daniel Hanych | First Assistant "A" Camera |
| Production | Dominic Rustam | Co-Producer |
| Art | Julie Hook | Art Department Coordinator |
| Art | Héctor B. López | Assistant Property Master |
| Camera | Seth A. Peschansky | First Assistant "B" Camera |
| Sound | Michael Krikorian | Utility Sound |
| Camera | Deepak Whitesides | Grip |
| Directing | Liz Trainor | Script Supervisor |
| Camera | Seth Kotok | Second Assistant "A" Camera |
| Lighting | Juan Barroso | Electrician |
| Costume & Make-Up | Hana Rausalova | Costume Supervisor |
| Sound | Charlie Kolander | Dialogue Editor |
| Sound | Chad J. Hughes | Supervising Sound Effects Editor |
| Sound | Greg Steele | ADR Mixer |
| Crew | John C. Hartigan | Special Effects Coordinator |
| Sound | Aaron Levy | Sound Supervisor |
| Production | Javier Robles | Assistant Location Manager |
| Production | Charissa McLain | Production Coordinator |
| Editing | Rob Sciarratta | Colorist |
| Production | Paul Codiga | Location Manager |
| Production | Mike Barry | Assistant Location Manager |
| Production | JT Panzarella | Assistant Location Manager |
| Sound | Alexandra Fehrman | Sound Editor |
| Sound | Tami Treadwell | ADR Mixer |
| Visual Effects | Vico Sharabani | Visual Effects Supervisor |
| Editing | Perri Pivovar | Assistant Editor |
| Sound | Alexandra Fehrman | Sound Supervisor |
| Sound | Vincent Guisetti | Foley Artist |
| Sound | Ron Bedrosian | ADR Mixer |
| Sound | Leobardo Ledon | Foley Editor |
| Crew | Beverley Hartigan | Special Effects Coordinator |
| Sound | Ruth Adelman | ADR Supervisor |
| Sound | Geordy Sincavage | Foley Mixer |
| Production | Traci Tateyama | Assistant Production Coordinator |
| Crew | Eric Wills | Craft Service |
| Editing | Elana Joy Livneh Lessem | Assistant Editor |
| Sound | Tom Paul | Sound Re-Recording Mixer |
| Sound | Sean Garnhart | Sound Re-Recording Mixer |
| Sound | G.W. Pope III | Foley Artist |
| Directing | Casey Mako | Second Second Assistant Director |
| Production | Freya Krasnow | Casting Assistant |
| Production | Debe Waisman | Extras Casting |
| Visual Effects | Simone Metzger | Visual Effects Coordinator |
| Crew | Matthew Ballard | Transportation Captain |
| Crew | Phil Eisenhower | Studio Teacher |
| Sound | Steve Papagiannis | Sound Effects Editor |
| Sound | Jake Monaco | Original Music Composer |
| Production | Nicolas Chartier | Producer |
| Production | Mary Viola | Producer |
| Production | Craig J. Flores | Producer |
| Editing | Catherine Haight | Editor |
| Production | McG | Producer |
