In the Old Testament, God demands that Abraham sacrifice his son. That’s a heck of a dilemma. Abandon a god with whom you have a loving relationship or murder your son. Personally, intolerable. But story gold.
Writers have been using dilemmas since the very beginning. In general, it’s about having to choose between to horrible, irreversible alternatives. Sophie’s Choice includes a powerful example. She must decide who will live, her son or her daughter.
Extreme choices reveal character, both in terms of how the choice is arrived at and in terms of the aftermath, how the person deals with its consequences — especially psychologically.
Abraham chooses God, confirming his faith. He is stopped from sacrificing his son and, through his son, becomes the patriarch of a great nation. Sophie sees her daughter taken away to her death and is traumatized. She becomes an alcoholic and kills herself.
As a writer, giving characters dilemmas forces dramatic story choices because it evokes emotions — in you and your readers.Explorations that would otherwise become impossible become necessary. (That is, unless you fudge it by some device like time travel. That trope is called upon in Harry Potter and isn’t a complete failure because the mechanism is foreshadowed effectively. In Superman, where the hero gets both choices by making the world spin backward, all the drama and joy of the movie is sucked away.)
To create a dilemma, it is essential to know who the character is and what he or she values deeply. (The biggest writing failure is making the dilemma too trivial. Some writers have a difficult time making things tough for their characters.)
The dilemma should be between two bad options, not two good. I had a friend who had to choose between attending Johns Hopkins Medical School and the University of Pennsylvania’s med school. It caused her some stress, but was not the stuff of great drama.
While the main character may lack some knowledge, it’s best if the choice is not driven by the character being TSTL (too stupid to live).
The choice must be clear. There can’t be a third option or a compromise choice. It might be necessary to consult with other people to identify and close down creative opportunities.
The choice must be irreversible. This may take some thought. Many times, I’ve worked with writers who thought choices could not be reversed. But readers are very good as sniffing out ways they can be. A dilemma must put the character into a new world and make the old world inaccessible. Ideally, that new world will come with some surprises. Unintended consequences are a good thing in stories.
When the character makes the choice, it must be “in character.” While
before the choice is made the readers must doubt which way the character
will go, afterward it’s best to see the choice made as being
inevitable. (This is very difficult to pull off, and works best if
plants that point to the decision, such as an earlier decision, come
earlier in the story. Another good way to make it work is by buttressing
the decision after the fact. For instance, a friend saying something
like “I knew you’d make the right choice” can make it easier for the
reader to believe the decision.)
Ideally, the choice should do more than change the fortunes of the character. It should be tied to his or her flaws and change them as people, too.
Sometimes a dilemma only emerges after a series of small choices lead
the character into a corner. Think of stories where a less than alert or
willing to compromise character takes the bait and ends up beholden to a
There are what I call dilemma plus stories. In most cases, these include a choice that seems awful, but has a logical bonus that makes a happy ending possible. But it is also possible to make things go very bad.
What is a dilemma for a character may not be a dilemma for readers. Irony may be in play, either because the reader has superior knowledge or, more interesting, because the reader’s values clash with those of the character.
The potential for dilemmas in a story may not be obvious. It's worth looking more closely at the important choices your characters make to see if they can be constrained in ways that force dilemmas. This takes some courage because, ultimately, it will take you, as a writer, into uncomfortable territory. But it will pay off in terms of reader engagement and deeper insights.