A young man meets and instantly falls in love with an engaged woman.
Unfortunately the movie Playing It Cool is not yet available on HBO Max.
| 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 |
