Playing It Cool is a 2014 romantic comedy directed by Justin Reardon and starring Chris Evans and Michelle Monaghan, with Ioan Gruffudd, Luke Wilson, Topher Grace, Aubrey Plaza, Peyton List, Anthony Mackie and Philip Baker Hall appearing in supporting roles.
The film centers around "Me" (Evans), a screenwriter who has to write a romantic comedy. The problem is that he has no idea what love is, and his friends are of very little help in improving his understanding of the emotion/concept. Then "Me" meets "Her" (Monaghan) at a charity event, finds himself dealing with feelings he's 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 Me'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 Me'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 Me for taking too long to write their movie.
- Better than a Bare Bulb: Me and his friends are all writers so they frequently bring up and discuss the shortcomings of various romantic comedy tropes.
- Berserk Button: Me 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 Me (with whom she's got great personal chemistry, but who is also childish and unreliable) as "Veronica." She eventually chooses Me, and he is shown to at least be working on overcoming his flaws.
- Central Theme: Should the Me 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. Me eventually chooses the second option, but we don't get to see how it turns out.
- Chekhov's Gun: The montage of alter egos Me goes through at the beginning of the film all play a role in his growth as a character later on.
- Curb-Stomp Battle: Me 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 Me collapses and pukes all over Stuffy's shoes.
- Double Standard: Me and Her have a snarky conversation about a few of these early on. Me 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, Me 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: Me 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: Me, Her, and Stuffy aren't addressed by name at any point in the film or in the credits.
- Parental Abandonment: Me'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 Me 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.
- Wimp Fight: Me and Stuffy get into a fistfight. Me is so drunk that he doesn't even get to throw a punch. Stuffy gets in two hits before Me 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 Me decides that his circle of friends is to him, and that he needs to take better care of them.