Story Structure: The Art of the Dilemma

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Having strong dilemmas is the key to a successful TV pilot. A dilemma is when your lead character is forced into a choice where neither choice is a good one; in other words, there is not a clear choice. They are caught “between a rock and a hard place.” By starting your show with a powerful dilemma or a series of strong dilemmas, you elevate the chances of the series succeeding.

When I came to the recognition that having a strong dilemma is the key component of the setup in each story arc, my perspective opened up. I teach the idea that if you have a powerful enough dilemma at the opening of your TV pilot, the series should be the answer to the dilemma. This idea is perfectly executed in the series premier of The Good Wife. The starting dilemma is one that the central character, Alicia, faces after her husband is involved in a sex scandal and is sentenced to prison. What does she do to bring security back to her family? The answer to this dilemma is what the series is about. Alicia goes back to a law career that she abandoned thirteen years earlier.

As a story consultant and writing instructor for Writers on the Verge at NBC, I’ve seen first hand how having strong dilemmas at the beginning of every story arc adds momentum, defines character, and offers a strong jumping off point for any successful TV series.

'Ray Donovan'

‘Ray Donovan’

In the new Showtime series, Ray Donovan, there are countless problems that lead into dilemmas. The show illustrates how having strong professional and personal dilemmas, increases a series’ chances of capturing an audience and making them want to come back. The series premier kicks off with a range of dilemmas including Ray’s father getting out of jail, Ray’s celebrity client waking up with a dead woman in his bed, Ray’s brother Bunchy being molested by a priest, his father killing the wrong priest, his wife struggling with the neighbor’s loud music, his daughter working on a family tree, his brother Terry having Parkinson’s, and his employer Lee Drexler’s dilemma with his client Tommy Jenkins. These dilemmas will spark the principal characters to take action. This group of dilemmas and problems are revealed in the first nine pages of the script. Some of these dilemmas are series/season 1 dilemmas and some of them are episode dilemmas. The gift of each one is that they start each story/character arc in a way that makes you want to see more.

Let’s start by looking at the series arc dilemma. Ray’s father, Mickey, gets out of jail. This is the trigger incident for the series. The early release of his father creates havoc on Ray’s family. We understand just how much as the episode progresses. We learn that there is an estranged and dysfunctional relationship between Ray and his father. So, by showing his release at the beginning, we are seeing part of the wound that will drive Ray. Then, when his father, newly released from prison, shoots a priest, we know that the stakes will escalate. We learn that Mickey thought it was the priest who molested his son, Bunchy. The twist is that he murdered the wrong priest. This action will clearly build during the season.

Ray faces a professional dilemma with his celebrity client Deonte, who wakes up with a dead woman in his bed. We learn that Deonte just signed an 80 million dollar contract, a nugget of information that clearly raises the stakes. Deonte claims that he didn’t kill the woman and that he didn’t even get to have sex with her because of the drugs. What we learn with this dilemma is the premise of the show. This is what Ray Donovan does for a living: he helps celebrity clients out of problems. This dilemma is quickly solved by another dilemma involving Tommy Jenkins, a young Hollywood star and a client of attorney (and Ray’s employer) Lee Drexler. Tommy has a 200 million dollar heterosexual movie coming out in a month and decides to pick up a tranny on Sunset Blvd. Ray, and his team of investigators, quickly sweep up this mess by tying Tommy to the scene with the dead woman. It is established that she overdosed and wasn’t killed. Ray kills two birds with one stone: he gets Deonte out of trouble and saves Tommy from losing his heterosexual image. These dilemmas are solved at the beginning. They set up what the series will be.

The dilemma Ray faces with his brother Bunchy surfaces when Bunchy receives a 1.4 million dollar settlement for the pain and suffering brought on by childhood abuse at the hands of a priest. Bunchy, who uses alcohol to numb the pain, refuses Ray’s offer to help manage the money. This shows us that Ray may be strong and resourceful when it comes to fixing his clients’ problems but when it comes to his own family, fixing the problems doesn’t come as easily. This goes into the central conflict for Ray.

We see the personal and the professional clashing again when Ray faces a dilemma with his next client, Stu Feldman, a guy who Ray’s wife wants him to talk to about getting his daughter into a prestigious school. Stu hires Ray to spy on his girlfriend, Ashley, because he thinks that she is carrying on behind his back. Stu is also married. While Ray watches Ashley’s place, he sees that she has a stalker. Rather than stay loyal to Stu who hired him, Ray goes to Ashley to tell her that she has a stalker. We learn that Ashley and Ray have a history. Ashley quickly connects how Ray discovers that she has a stalker: Stu hired him to watch her. She reacts to this. Ashley gets seductive with Ray. In the midst of making out, Ashley has a seizure. This dilemma leads to a conflict between Ray and his wife, Abby, when she and Ashley meet at a yoga class.

All of these dilemmas build the strength of the show, add momentum, define the characters and make it a show that the audience wants to return to every week. It all comes down to the art of how you craft your dilemmas around each story and character arc.

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3 thoughts on “Story Structure: The Art of the Dilemma

  1. robertswww

    Nice article on integrating dilemma into your story arcs. If an important decision is too easy, then there is no drama and little payoff for the viewing audience.

    I love it when characters are pushed into a corner facing a situation they would rather avoid with no easy way out. A good dilemma can make the viewer squirm and wonder what they would do if they found themselves in such a situation.

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