Playing It Cool is a 2014 American romantic comedy film directed by Justin Reardon and written by Chris Shafer and Paul Vicknair. The film stars Chris Evans and Michelle Monaghan. The film was released on video on demand on March 31, 2015 before a limited release on May 8, 2015 by Vertical Entertainment. It received generally negative reviews from critics.

Christopher Robert Evans is an American actor. He began his career with roles in television series such as Opposite Sex in 2000. Following appearances in several teen films, including 2001's Not Another Teen Movie, he gained attention for his portrayal of Marvel Comics character the Human Torch in Fantastic Four (2005) and Fantastic Four: Rise of the Silver Surfer (2007). Evans made further appearances in film adaptations of comic books and graphic novels: TMNT (2007), Scott Pilgrim vs. the World (2010), and Snowpiercer (2013).