Today, we’re studying compelling character construction through the lens of a dilemma. We’ll explore how a well-constructed dilemma can make a story memorable. Although one of the most unforgettable and diabolical dilemmas in all of film occurs in Sophie’s Choice, I have written about the film before. Today, therefore, we’re exploring its power through five building-blocks at work in Martin Scorsese’s gripping film, The Departed.

1. High Stakes/Risk

Our first building-block is high stakes—the higher the stakes or risk, the more gripping the dilemma, the more powerful the drama. In The Departed, the character Billy Costigan faces an immediate and life-altering choice. Should he betray his undercover identity and risk his life to expose the mole in the police force, or should he continue to play the dangerous game of deception? The stakes in the story are high indeed—exposure will result in death, but doing nothing risks the safety and integrity of the operation.

As writers we ought to create dilemmas where the consequences of the characters’ choices are strongly felt by the audience.

2. A Conflict with Morality

The conflict with morality lies at the centre of many compelling dilemmas. The Departed feeds on the moral ambiguity exhibited by Colin Sullivan. He is an undercover cop playing the role of a criminal, and has to grapple with the morality that his role forces on his day-to-day choices. Does he stay loyal to the criminal organisation that raised him, or does he betray it for the impersonal notion of justice and personal gain?

This moral tug-of-war keeps the audience engaged it bears witness to the internal struggle that defines Sullivan’s character. As writers, we ought to dig into the moral complexities of our characters, forcing them to confront their values and weaknesses as they make decisions that challenge their integrity and existence.

3. Personal vs. Public Interests

The third building-block involves the clash between personal and public interests. In The Departed, the characters are trapped in a web of competing loyalties: Does Sergeant Dignam reveal the truth about the mole within the police force at the cost of endagaring his own safety and that of his colleagues? Quite the dilemma.

This conflict between personal loyalty and the greater public good adds complexity to the story. As writers, we ought to create dilemmas that force characters to question allegiances by exploring the tension between what is best for themselves versus what is best for the wider public.

”A strong character dilemma is one of the most effective ways to showcase internal and external conflict within a single character, and have it spread to other characters, heightening the tension and forward thrust of the story.“

4. Time Sensitivity

A ticking clock intensifies the pressure to resolve a dilemma by forcing the action. In the film, the characters are constantly up against the clock in trying to find the mole. The longer it takes, the more lives are put at risk, the greater the chance of being exposed.

The urgency drives the story forward relentlessly, creating a sense of immediacy that keeps the audience captive. We too should use time as a tool, trapping our characters in tight spots where each minute, each hour places them in a more precarious situation, and where every decision carries serious, perhaps even life-threatening, consequences.

5. Unpredictability

The outcome of any great dilemma should not be predictable. In The Departed, the true identities of the mole and the undercover cop are shrouded in mystery. This uncertainty heightens the tension, leaving the audience guessing, until the final, shocking moments when the truth is revealed.

As writers, we ought to use the unexpected, crafting twists and turns that complicate our characters’ dilemmas and keep readers and viewers on edge. The surprise that occurs when the dilemma is finally resolved, can be a powerful tool in crafting memorable and impactful stories.

Summary

Use five building-blocks to craft a powerful dilemma: high stakes, morality, personal vs. public, time sensitivity, and unpredictability. This will enrich our characters and make our stories more memorable.

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