Playing It Cool is a romantic comedy starring Chris Evans and Michelle Monaghan. Ioan Gruffudd, Luke Wilson, Topher Grace, Aubrey Plaza, Anthony Mackie and Philip Baker Hall appear in supporting roles.
The film centers around The Narrator (Evans), a screenwriter who has to write a romantic comedy. The problem is that he has no idea what love is and his friends aren't much help in improving his understanding of the emotion/concept. Then The Narrator meets Her at a charity event and he finds himself dealing with feelings he never experienced before and is immediately smitten with the woman. There's a wrinkle, however: Her has a boyfriend.
This film provides examples of:
- Artistic License History: Granddad's derring-do story about wooing The Narrator's grandmother during World War II is anything but historically accurate let alone plausible.
- Art Shift: Granddad's story about World War II is animated.
- As Himself: Matthew Morrison and Ashley Tisdale appear as figments of The Narrator's imagination and act out the parts he's writing for them as he works on his computer. They also appear in a nightmare threatening to kill The Narrator for taking too long to write their movie.
- Better Than a Bare Bulb: The Narrator and his friends are all writers so they frequently bring up and discuss the shortcomings of various romantic comedy tropes.
- Berserk Button: The Narrator can't even look at a box of Cap'n Crunch because his mother stuck her goodbye note onto a box when he was a child.
- Betty and Veronica: Her has to choose between Stuffy (who offers her everything she wants in a life partner, but who also apparently bores her enough to make her flirt with strange men at parties) as "Betty" and the Narrator (with whom she's got great personal chemistry, but who is also childish and unreliable) as "Veronica." She eventually chooses the Narrator, and he is shown to at least be working on overcoming his flaws.
- Central Theme: Should the Narrator stay out of Her's life (which may be a cowardly decision that could cost both a chance at true love and lasting happiness) or try to convince her to be with him (which may be a selfish decision that could mess up the imperfect but functional life she has built for herself)? Different characters have different opinions, and several even change them throughout the movie. The Narrator eventually chooses the second option, but we don't get to see how it turns out.
- Chekhov's Gun: The montage of alter egos The Narrator goes through at the beginning of the film all play a role in his growth as a character later on.
- Double Standard: The Narrator and Her have a snarky conversation about a few of these early on. The Narrator complains that he doesn't get ogled and objectified enough, while Her laments that men just want her for her body instead of wanting her for her money.
- Earn Your Happy Ending: In the final scene, the Narrator tells Her that they may well end up making each other miserable but he still wants to try, and convinces her to give their relationship a shot. The movie ends abruptly there, leaving it unsaid how it turned out.
- Freudian Excuse: The Narrator is cynical about love because his mother abandoned him when he was a child to move to Chile with her boyfriend. He believes that if something as pure as the connection between a mother and child can be broken so easily, then there's no hope for a romantic relationship.
- No Name Given: The Narrator, Her, and Stuffy aren't addressed by name at any point in the film or in the credits.
- Parental Abandonment: The Narrator's mother walked out on him when he was just a child.
- Parental Substitute: Granddad stepped in to raise The Narrator.
- Rated M for Manly: When the Narrator complains that Granddad's story sounds like a Disney movie, Granddad insists that it's in fact a very manly story and starts adding a lot of action and feats of badassery that he supposedly performed. As a result, the Narrator starts imagining it as an over-the-top-macho comic book full of blood and explosions, with a muscular, bare-chested Perpetual Frowner protagonist.
- Reality Ensues: The Narrator briefly fantasizes about kicking Stuffy's ass before coming back to the reality that he's very drunk and can barely stand. Stuffy gets in two solid blows before The Narrator collapses and pukes all over Stuffy's shoes.
- Wimp Fight: The Narrator and Stuffy get into a fistfight. The Narrator is so drunk that he doesn't even get to throw a punch. Stuffy gets in two hits before the Narrator pukes all over his shoes, causing him to stomp off complaining about how the stain probably won't come out of the suede.
- True Art Is Angsty/True Art Is Incomprehensible: In-Universe. No one knows what Mallory is trying to express in her one woman shows. The only thing that's clear in the show seen in the movie is that it has something to do with the trauma of childbirth.
- True Companions: What the Narrator decides that his circle of friends is to him, and that he needs to take better care of them.