The Expanded Ultimate Story Checklist: Does the outcome of the scene ironically reverse and/or fulfill the original intention?

As we’ve now established, irony is the heart of meaning, and it should suffuse every aspect of your story. This means you need to keep upsetting your heroes’ expectations, but it doesn’t mean your heroes need to keep failing. 

Audiences love to see characters succeed or fail in ironic ways. That’s what keeps stories interesting. If a girl says to the glum boy she likes, “I’m going to take you to the carnival and cheer you up,” then the audience is not going to want to see either a straightforward success (he loves the roller coaster and thanks her for a fun time) or a straightforward failure (he hates the rides and says, "Thanks for nothing.").

The audience would much rather see one of the following:

• An Ironic Failure: He loves the rides and starts to cheer up, but from the top of the Ferris wheel he spots his ex kissing a new guy behind the ring toss, and he becomes more depressed than ever. 
• An Ironic Success: He hates the rides and tries to sneak away, but as he does so, he sees a carnie kicking a mangy dog out of the camp, so he rescues the grateful dog, who proceeds to make him totally happy. 

In Romeo and Juliet, Romeo doesn’t go to the party to meet someone new. He goes to win back Rosaline’s affections. He finds the love he craves, but he does so ironically. He forgets his former infatuation and finds someone new.

This is another thing to be aware of when it’s time to turn your outline into a finished project. The broad strokes of the scene may be “He goes to the party, meets Juliet, and falls in love,” but when you’re painting in the details, you should make it more interesting. Try to have every plot point, positive or negative, be an ironic reversal of what the audience and the character expected. Your audience will love you for it.

Scenes that lack irony can do real harm to a story. Look at any scene involving a misunderstanding. Captain America was a lot of fun, but the weakest plot turn in that movie showed the danger of relying on an unironic misunderstanding.

At mid-movie, everything is hunky-dory with Cap and his love interest. They’re both supernice and only interested in each other, so there’s no room for any real drama in their relationship. But the writers nevertheless felt the need to put a bump in the road, so they fell back on an old standby. Out of nowhere, a vixenish secretary grabs Cap for an unwanted passionate kiss just as he’s leaving the war office. Before he can push her away, his crush walks in, sees them together, and then runs away. Ugh.

This false conflict could be resolved with a simple explanation, but, as usual, the misunderstanding snowballs out of control. Why do this? Why not generate an actual difference of opinion between the two so a genuine dilemma can help fuel the drama instead of a meaningless mix-up?

The Apartment, on the other hand, shows the value of an ironic misunderstanding. Baxter’s neighbor spends the entire movie convinced that Baxter, and not his bosses, is bringing all those women back to his apartment. This adds a thick layer of irony to their discussions.

Baxter accepts the criticism because he wants to be gentlemanly and to conceal his bosses’ affairs, but as a result, he looks like a massive heel. The audience bristles with indignation to hear our hero falsely accused, but we also know Baxter’s actions are wrong and he does deserve criticism, even if it’s misdirected.

This irony is compounded when Baxter’s boss, Sheldrake, jilts his mistress and she attempts suicide in Baxter’s apartment. When the doctor comes over to help, Baxter covers for Sheldrake and claims that he jilted her. As the doctor’s criticisms get more severe, Baxter must totally adopt the persona of his boss, quoting Sheldrake’s dismissals of her as if they were his own.

This attempt to identify with his boss has the opposite effect on Baxter: It forces him to finally realize just how despicable Sheldrake is. Baxter has to become what he fears, which shows him what he really wants to be. It also results in the advice he most needs to hear, even if he hears it for the wrong reason: “Be a mensch.”

Imagine a different version of this scene: Baxter truthfully explains the situation, and the doctor sympathetically suggests that Baxter should stand up to his terrible boss. That would be far less powerful.

The misunderstanding in Captain America is not ironic and tests the audience’s patience. The many misunderstandings in The Apartment are wickedly ironic, juicing every scene with additional layers of meaning. 

Rulebook Casefile: Ironic Positive Developments in Humans of New York

This post from “Humans of New York” exemplifies two rules: The importance of an “I understand you” moment at the beginning of a romance, and the importance of ironic positive developments. Presumably, both men came to the party determined to be antisocial sticks-in-the-mud, and then the two sticks saw each other across a crowded room. (Fun fact: I used to write songs in college, and one had the chorus “I don’t care and you don’t care so let’s not care together”)

For this Scenework series, we’re examining these scenes:

The 40 Year Old Virgin	Andy goes home with a drunk woman from a Bachelorette party.
Alien	After the deaths of Kane, Brett and Dallas, Ripley becomes captain, so she has a meeting with the other survivors, Ash, Parker, and Lambert, to decide what to do next.
An Education	Jenny is amazed as David gets permission from her parents to take her on a weekend trip to Oxford by claiming to know C.S. Lewis.
The Babadook	Amelia chases her son Sam down to the basement, where he knocks her out, ties her up, and drives the Babadook out of her, temporarily.
Blazing Saddles	Bart arrives in town, then takes himself hostage to save himself from hostile townspeople
Blue Velvet	Jeffrey spies on Dorothy and Frank, then Dorothy catches Jeffrey in her apartment and has sex with him at knifepoint.
The Bourne Identity	Jason and Marie are attacked at her family’s farm by the assassin known as The Professor. Jason blows up a propane tank to distract him and kills him, but as the Professor dies he convinces Jason to come back.
Bridesmaids	Annie is driving angry after feuding with Helen when she gets pulled over by a cute cop, who gives her his number under the pretense of recommending a place to get her tail light fixed.
Casablanca	Sketchy crook Ugarte asks cool club owner Rick to hold onto the letters of transit for him.
Chinatown	Jake confronts Noah Cross with the glasses
Donnie Brasco	Lefty seeks to go behind Sonny Black’s back to set up his own meeting in Florida with Trifficante. He has Donnie borrow a boat for this purpose, but Sonny Black knows everything, and he crashes the party.  Lefty bitterly assumes that Donnie has betrayed him, and shuns him.  Sonny takes Donnie aside and elevates him above Lefty.
Do the Right Thing	Buggin’ Out notices that there are no brothers on the wall of Sal’s Pizzeria and decides to organize a boycott.
The Farewell	Billi finds out about Nai Nai’s diagnosis from her parents.
The Fighter	Micky and Charlene confront Micky’s family about his career.
Frozen	Anna confront Elsa in her ice palace
The Fugitive	Gerard confronts Kimble atop a dam, but Kimble leaps off.
Get Out	Chris sneaks out for a smoke in the night, has creepy encounters with Georgina and Walter, then finds Missy drinking tea.  She implores him to sit down, he repeats that he doesn’t want to be hypnotized, but she does it anyway with her teacup.  She gets him to admit the facts of his mother’s death, then sends him to a “sunken place” in his mind.
Groundhog Day	Phil takes Rita to a cafe and tries to convince her that he’s living the same day over and over. He convinces her by predicting what Larry will say.
How to Train Your Dragon	Hiccup and his students are in an arena competing to defeat a dragon, but Hiccup is quizzing their instructor to find out how to better commune with his own dragon, Toothless. Along the way, he uses what he learned from Toothless to peacefully subdue the dragon they’re fighting, infuriating the others.
In a Lonely Place	Laurel has made secret plans to leave town, but Dix makes her go to his favorite restaurant to celebrate their engagement with his agent, his alcoholic friend, and others.
Iron Man	Tony has built a better chest-device to keep shrapnel out of his heart, so he calls Pepper in to reach into his chest and replace the old one with a new one.
Lady Bird	Lady Bird flirts with Kyle in the parking lot.
Raising Arizona	During Hi and Ed’s first night with Junior, brothers Gale and Evelle show up having just escaped from jail, and begin to suspect the truth.
Rushmore	Max introduces himself to Ms. Cross on the bleachers.
Selma	King meets with Johnson in the Oval Office to try to get him to commit to a new Voting Rights Act
The Shining	Jack finally takes a drink from the ghosts in the ballroom. A waiter spills a drink on him, and takes him to the bathroom to clean it off.  While he does so, Jack realizes that the waiter is actually Grady, the former caretaker that killed his family.  Grady encourages him to do the same, but Jack is uncertain.
Sideways	Miles has struck out with Maya, but Jack comes back to the motel after a wild night with Steph, intending to go back out. Miles tries to get Jack to stay by forcing him to call his fiancé, but she doesn’t answer and Jack takes off with Steph after getting Miles to return his unused condom from the night before.
The Silence of the Lambs	Clarice first meets Lecter in his cell, under the pretense of getting him to fill out a questionnaire, but he quickly figures out that it’s really about Buffalo Bill, and that Clarice is hiding other things as well.
Star Wars	The gang takes over the Death Star command office.
Sunset Boulevard	Joe discovers Norma, who assumes that he’s there to plan her monkey’s funeral, but when he explains that he’s a screenwriter, she hires him to rewrite her screenplay for Salome instead.

So how do those scenes do with this question?

The 40 Year Old Virgin	YES, he turns her down.
Alien	NO. Not really.
An Education	YES.  David gets them to insist on it, and he “reluctantly” agrees.
The Babadook	YES. He drives the monster out of her but then it enters him.
Blazing Saddles	YES. He ends up in the sheriff’s office but as both hostage and villain, not as hero yet.
Blue Velvet	YES. he goes there to violate her privacy in secret but he winds up totally exposed.
The Bourne Identity	YES. the professor dies but ironically succeeds in bringing Jason in.
Bridesmaids	YES. Being pulled over by a cop turns out to be a good thing.
Casablanca	NO. Ugarte unironically gets what he wanted.
Chinatown	YES. Cross has trapped Gittes instead of the other way around.
Donnie Brasco	YES.  Donnie wanted to advance along with Lefty, but instead he advances by unwittingly betraying Lefty.
Do the Right Thing	NO. Not really.
The Farewell	YES. She finds out the truth but humiliates herself in the process, admitting to her powerlessness.
The Fighter	YES. Micky and Charlene came to confront the family, but they get sucked in.
Frozen	YES. It’s not really ironic, she just fails.
The Fugitive	YES. Thought he was chasing a killer, but instead he seems to have become the killer himself.
Get Out	YES. She promised him more self-control and left him with none.
Groundhog Day	NO. it’s pretty unironic. He does exactly what he sets out to do.
How to Train Your Dragon	YES. He’s trying not to fight, but he’s the one that defeats the dragon.
In a Lonely Place	YES. the celebration ruins everything.
Iron Man	YES. He saves his heart and loses it.
Lady Bird	Not really.
Raising Arizona	YES. They were afraid it would be someone who wanted to send them to prison, but it was friends, but the friends also seem destined to send them back.
Rushmore	NO. it all goes according to plan.
Selma	YES. They each wanted to move the other to join their side but each fails.  Johnson tries to quiet King down but riles him up.
The Shining	YES. Jack comes in to be served by the house, ends up serving it.
Sideways	NO. Not really. Jack gets what he wanted unironically, Miles’s “check your messages” ploy fails, but it’s not ironic, it’s just bad luck.
The Silence of the Lambs	YES. She gets what she wants by giving in rather than standing her ground.
Star Wars	YES. They find a secure place to hide, then they decide to leave.
Sunset Boulevard	YES. he starts by mocking her dead monkey, then becomes her new monkey.