Romantic comedies have become so old-hat that a new one, Playing it Cool, seeks to parody the genre while delivering precisely what it is parodying. It’s a fine line to keep when self-parody is involved, and this film sometimes strays off of that line, but it’s an entertaining attempt to have a little fun with familiar customs and conventions while still delivering sentiment, humor and romance.
Justin Reardon’s film presents Chris Evans as a screenwriter (and the film’s narrator) given an assignment to write a rom-com. The problem is that Evans is not at all romantic, and doesn’t know how to proceed. His writing friends (Topher Grace, Luke Wilson, Aubrey Plaza, Martin Starr) and his agent (Anthony Mackie) try to help, but nothing works until he meets Michelle Monaghan, with whom he finally develops an actual relationship. Of course she is engaged, and serious about it, so his feelings for her trigger anxiety and depression as well as joy.
The clever script is full of banter, shots at the conventions of romance and romantic stories, talk of sex and a rudimentary exploration of scriptwriting. Having the writing friends around really helps, and the narration is so self-effacing that Evans’ rather troubled character is presented with necessary humility and pathos. Ultimately, of course, the formula must be followed, and the film lurches to its inevitable romantic climax, passing the opportunity to allow Evans and Monaghan to separate as friends whose timing just wasn’t quite right as a couple. Oh well, another happy ending.
Monaghan is especially appealing here, a charming woman who isn’t afraid to let her guard down and have fun, as long as things don’t get too crazy. We get the feeling that she is a far better person than Evans, but that her influence on him may be the best thing that could happen to him. Reardon makes great use of San Francisco locales and tries really hard to keep his script fresh and funny. Some of it is forced, and another draft or two may have been able to smooth out the bumps that remain, but I enjoy the film for what it does right. ☆ ☆ 1/2. 18 May 2015.