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 |
| Writing | Chris Shafer | Screenplay |
| Directing | Justin Reardon | Director |
| Production | Chris Evans | Executive Producer |
| Production | Mary Viola | Producer |
| Editing | Catherine Haight | Editor |
| Production | McG | Producer |
| Production | Nicolas Chartier | Producer |
| Production | Craig J. Flores | Producer |
| Sound | Jake Monaco | Music |
| Production | Nicolas Chartier | Executive Producer |
| Production | Jon Poll | Co-Executive Producer |
| Production | Dominic Rustam | Co-Producer |
| Production | Corrie Rothbart | Co-Producer |
| Production | Bruce Wayne Gillies | Line Producer |
| Production | Kim Davis-Wagner | Casting |
| Production | Justine Arteta | Casting |
| Camera | Jeff Cutter | Director of Photography |
| Art | Patrick Lumb | Production Design |
| Costume & Make-Up | Beth Pasternak | Costume Designer |
| Sound | Gabe Hilfer | Music Supervisor |
| Sound | Kevin J. Edelman | Music Supervisor |
| Production | Bruce Wayne Gillies | Unit Production Manager |
| Directing | Rod Smith | First Assistant Director |
| Directing | Jasmine Marie Alhambra | Second Assistant Director |
| Production | Chris Shafer | Co-Producer |
| Production | Paul Vicknair | Co-Producer |
| Editing | Lara Khachooni | Additional Editor |
| Production | Jennifer Haire | Production Supervisor |
| Crew | Larry Ferguson Jr. | Post Production Supervisor |
| Crew | Kelley Cribben | Post Production Supervisor |
| Sound | Aaron Levy | Sound Designer |
| Crew | Andy Cheng | Stunt Coordinator |
| Art | Julie Hook | Art Department Coordinator |
| Art | Justin Reardon | Storyboard Artist |
| Art | Lisa Clark | Set Decoration |
| Art | Douglas Woods | Set Dresser |
| Art | Yoel Ancieta | Set Dresser |
| Art | Myles Lumb | Set Dresser |
| Art | Patrick Lumb | Set Dresser |
| Art | Michelle Waring | Art Department Assistant |
| Art | Gregory R. Wolf | Property Master |
| Art | Héctor B. López | Assistant Property Master |
| Art | Greg Manke | Props |
| Camera | Timothy Roarke | Camera Operator |
| Camera | Daniel Hanych | First Assistant "A" Camera |
| Camera | Seth Kotok | Second Assistant "A" Camera |
| Camera | Gavin Ames | Steadicam Operator |
| Camera | John Waldo | First Assistant Camera |
| Camera | Seth A. Peschansky | First Assistant "B" Camera |
| Camera | Daniel C. McFadden | Still Photographer |
| Sound | Pawel Wdowczak | Sound Mixer |
| Sound | Tim Song Jones | Boom Operator |
| Sound | Michael Krikorian | Utility Sound |
| Lighting | Bobby Wotherspoon | Chief Lighting Technician |
| Lighting | Luke Kalarickal | Assistant Chief Lighting Technician |
| Lighting | Juan Barroso | Electrician |
| Lighting | Wadsworth Peters | Electrician |
| Camera | William Buckingham III | Key Grip |
| Camera | Michael Orr | Dolly Grip |
| Camera | Brenden "Snake" Craighill | Grip |
| Camera | Deepak Whitesides | Grip |
| Directing | Liz Trainor | Script Supervisor |
| Costume & Make-Up | Hana Rausalova | Costume Supervisor |
| Costume & Make-Up | Adrienne Greshock | Key Costumer |
| Costume & Make-Up | Debbie Travis | Key Costumer |
| Costume & Make-Up | Unchin Lee | Set Costumer |
| Costume & Make-Up | Steve Constancio | Set Costumer |
| Costume & Make-Up | Charlotte Parker | Hair Department Head |
| Costume & Make-Up | Deborah Rutherford | Makeup Department Head |
| Production | Paul Codiga | Location Manager |
| Production | Mike Barry | Assistant Location Manager |
| Production | JT Panzarella | Assistant Location Manager |
| Production | Javier Robles | Assistant Location Manager |
| Production | Charissa McLain | Production Coordinator |
| Production | Traci Tateyama | Assistant Production Coordinator |
| Directing | Casey Mako | Second Second Assistant Director |
| Production | Freya Krasnow | Casting Assistant |
| Production | Debe Waisman | Extras Casting |
| Crew | Eric Wills | Craft Service |
| Crew | Beverley Hartigan | Special Effects Coordinator |
| Crew | John Hartigan | Special Effects Coordinator |
| Crew | Matthew Ballard | Transportation Captain |
| Crew | Phil Eisenhower | Studio Teacher |
| Editing | Perri Pivovar | Assistant Editor |
| Editing | Elana Joy Livneh Lessem | Assistant Editor |
| Sound | Tom Paul | Sound Re-Recording Mixer |
| Sound | Sean Garnhart | Sound Re-Recording Mixer |
| Sound | Aaron Levy | Sound Supervisor |
| Sound | Alexandra Fehrman | Sound Supervisor |
| Sound | Chad J. Hughes | Supervising Sound Effects Editor |
| Sound | Steve Papagiannis | Sound Effects Editor |
| Sound | Alexandra Fehrman | Sound Editor |
| Sound | Ruth Adelman | ADR Supervisor |
| Sound | Ron Bedrosian | ADR Mixer |
| Sound | Greg Steele | ADR Mixer |
| Sound | Tami Treadwell | ADR Mixer |
| Sound | Charlie Kolander | Dialogue Editor |
| Sound | Geordy Sincavage | Foley Mixer |
| Sound | Vincent Guisetti | Foley Artist |
| Sound | G.W. Pope III | Foley Artist |
| Sound | Leobardo Ledon | Foley Editor |
| Editing | Rob Sciarratta | Colorist |
| Visual Effects | Vico Sharabani | Visual Effects Supervisor |
| Visual Effects | Simone Metzger | Visual Effects Coordinator |
