WHEN INSPIRATION STRIKES, it’s hard to resist the impulse to sit down and start pounding out your new play. Why fight your muse when you’re on to an idea that excites you so much you’ll set everything else aside to write it?

But there are good reasons to resist the temptation, energizing as it might be. One is to avoid a lot of pain on the back end when it comes time to revise your script. And if you are serious about writing plays that work, you will always have to revise. If you write purely from that spark of inspiration without any thought to your character’s history, their essential actions, the arc of their story, or even to your overarching theme — the reason you’re writing in the first place — then the revision will be painful. Invariably, such a process leads to a first draft that meanders from idea to idea and from scene to scene without a coherent structure or clear central action.

I know this because it’s how I used to write plays when I started out. I had no clue what the story was or where it was headed. I just knew I was interested in these characters and that somehow — I hoped — it would all work out. But it usually didn’t. I recall the absolute sense of exhaustion and frustration as I tried to wrestle one of my early plays into some shape that would work dramatically. In the end, I had to give up. There was simply no saving it, because I had not done the hard work required to think through what I was trying to say in the first place.

Yet, I also knew that I could not sit down and outline the story ahead of time, as I was frequently advised to do. I simply looked at the blank page and froze. And I suspect I’m not alone in that reaction. Not everyone is able to think in linear fashion about story structure, at least not starting out. For some of us, that’s a skill we develop over time.

WHERE TO BEGIN

Over the years, I’ve figured out that writing an outline isn’t impossible. It’s just that, for me, it can’t be the very first step. Rather, I need to know a lot more about the characters who populate my story before I can think about the structure of the story. And if I’m willing to invest a little labor into getting to know those characters intimately, very often the story begins to present itself. Any good story, after all, will spring from the primary character’s most compelling need. So the more you know about your character and their struggles before you start to write your play, the easier it will be to work it out.

Here, then, is a tool I often use to dive into the hearts and minds of my characters. What follows is the first installment in a two-part exercise I’ve offered in a number of workshops. Ninety-Nine Questions to Ask Your Character is an improvisation on paper, aimed at helping you tap your subconscious knowledge about the character you’re creating. The key to the exercise is to answer the questions as if you are the character. Respond as quickly as you can, without agonizing over the answers. Your first impulse is the best impulse, so go with it. You can always make adjustments later. If you get stuck or you think something doesn’t apply, go on to the next question.

Ideally, you would have someone read these questions to you while you write the answers in a notebook. But if you have to work alone, cut and paste the questions into a new document file, then go through them one by one, writing your responses. It may seem like an exhausting task, but you’ll be amazed at what you come up with.

The loss of her child is a defining moment for Alice in Bright Star, performed by West Orange (Fla.) High School at the 2018 International Thespian Festival.
The loss of her child is a defining moment for Alice in Bright Star, performed by West Orange (Fla.) High School at the 2018 International Thespian Festival. Photo by John Nollendorfs.

CHARACTER DEMOGRAPHICS AND FAMILY

1. What is your name?
2. How old are you?
3. Where were you born?
4. What did your father and mother do for a living?
5. Were you well off? Middle class? Impoverished?
6. Do you have siblings? If so, what are their names and ages?
7. Where do you fall in the birth order? The oldest, youngest? 
8. Which one of you is your mother’s favorite? 
9. Why?
10. How did you feel about that?

CHILDHOOD AND EDUCATION

11. When you were a child, what was one thing you could always be sure of?
12. What was something you were never sure of?
13. Where did you grow up? Is this a place you’d go back to now? Or avoid?
14. Do you still have friends there? Or family?
15. How did you do in school? 
16. What was your favorite subject?
17. What was your greatest talent?
18. What did you do badly?
19. If you did not do well in school, why not? Were you not interested, or did something interfere with your ability to work hard? 
20. How far did you advance in your education? 
21. If you went to college, where did you go? If you didn’t go, what were you doing in those years?
22. If you went to college, what kind of school was it?
23. How did you pay for it? 
24. What was your course of study?
25. Is that what you wanted to do, or did someone influence you to follow that course?
26. How do you feel about those years now? Do you look back with pride or regret?

Very different childhoods shape the young contestants of Denver School of the Arts' 2018 ITF performance of The 25th Annual Putnam County Spelling Bee.
Very different childhoods shape the young contestants of Denver School of the Arts' 2018 ITF performance of The 25th Annual Putnam County Spelling Bee. Photo by Susan Doremus.

CURRENT HOUSEHOLD AND RELATIONSHIPS

27. What is your life like at the moment?
28. Are you married, single, or in a relationship?
29. What is that person’s name and occupation?
30. How are things going with him or her?
31. Where do you live now? 
32. What are your physical surroundings like? Are they comfortable, safe, or dangerous?
33. How do you feel about the place where you are now? Is there something you are particularly attached to, or particularly repelled by, in this place?
34. Who lives with you? 
35. How do you get along with them? If you don’t get along, what is the source of conflict?
36. Do you have children? 
37. If so, do you have a good relationship with them?
38. If not, what caused the rift?
39. How do they feel about you?
40. When is the last time you saw them?
41. What about the rest of your family? Are you close to them now or distant?
42. If you are distant, why? What has gotten in the way?

OCCUPATION

43. What do you do for a living? Are you self-employed, or do you work for someone else?
44. How long have you done this job?
45. Is this what you always planned to do, or did you fall into it?
46. How do you feel about it? 
47. Would you rather be doing something else? If so, what would it be?
48. If you’d rather be doing something else, what stops you? Is it money? Is it pressure from your family? Is it your own lack of self-confidence? Or does some other thing prevent you from doing what you want to do?
49. What would you have to change in your life in order to do that thing you’d rather do?
50. Does this change depend on someone else, or does it depend on you?

Their pioneering contributions to early 1900s astronomy distinguish the women of Mt. Carmel Academy's 2018 ITF performance of Silent Sky.
Their pioneering contributions to early 1900s astronomy distinguish the women of Mt. Carmel Academy's 2018 ITF performance of Silent Sky. Photo by Susan Doremus.

RELIGION AND SPIRITUALITY

51. What is your religious belief currently?
52. Do you still practice the religion of your youth, or have you left it behind?
53. If you left it behind, what caused you to do so?
54. Do you think you have the answers, or are you still searching?
55. If you are searching, where or how are you looking?

OTHER PERSONAL CHARACTERISTICS

56. How do you deal with stress? 
57. If you use drugs or alcohol, how do you feel about it? Do you brag about it? Try to hide it? Try to give it up and fail? Have no problem with it?
58. What do you do to entertain yourself? 
59. What is your idea of a really fun time? 
60. What do you consider to be your most admirable personal quality?
61. What is your greatest personal failing, in your view?
62. Do you think others see it that way, or would they say something different about your strengths and weaknesses?
63. How do you handle conflict with someone else? Do you avoid fights, or are you aggressive? Or are you passive aggressive and only give the appearance of cooperation?
64. What are your politics? Are you conservative, liberal, or something else? Do you have no interest in politics?

LOVE LIFE

65. What is your sexual orientation? Are you comfortable with it? 
66. If you are not comfortable with it, why not? 
67. What do you do about those negative feelings?
68. Do you have love in your life right now? 
69. Is there someone you once loved but no longer do?
70. If so, what happened to make that love go away?
71. What kind of problems do you face because of it?

PARENTAL BONDS

72. Are your parents still living?
73. If so, where are they now? Nearby or far away?
74. How often do you see them?
75. Do you want to see more of them or less?
76. If you want to see more of them, or less, why don’t you?
77. If your parents are critical of you, what choices have you made that displeased them? Was it your job, education, marriage, life partner, or political views?
78. Did their displeasure influence your decision? Did you decide to go ahead in order to show them up? Or did you change your mind because they disliked your choice?
79. If you changed your mind in order to please your parents, how do you feel about that now? 
80. How did they raise you as a child? Were they strict or lenient? Did they pay attention to you, or were they more interested in other things?
81. How did this affect your relationship with them then?
82. How does it affect your relationship now?
83. Does it affect your relationship with your own children?
84. If one or more of your parents are deceased, when did they die?
85. How did their death affect you? Did it change your life fortune? Were you forced to leave school? To give up a job? To abandon a plan? Or did you come into an inheritance?

A strong mother-daughter bond is central to the story of Steel Magnolias, presented at the 2017 ITF by Nordhoff High School. Photo by Susan Doremus.

FEARS, CHALLENGES, AND OBSTACLES

86. Where are you in your life right now? What are you most pleased with right now?
87. What keeps you awake at night?
88. What is the most pressing problem you have at the moment?
89. Is there something that you need or want that you don’t have? For yourself or for someone important to you?
90. Why don’t you have it? What is in the way?
91. What do you have to do in order to get the thing you need?
92. What is stopping you from taking this step?
93. Is there something else that must happen first in order for you to take this step?
94. Is there someone else who needs or wants the same thing?
95. Can they help you get it?
96. Are they one of the things in the way?
97. What happens if you don’t get it? What do you stand to lose?
98. How will your life change if you do get this thing or solve this problem?
99. Will someone else suffer if you succeed?

THE CHARACTER BIOGRAPHY

Having answered these questions, you can see that they are guiding you to a detailed character biography that you can use as a foundation for your play. You can work through this exercise for every character, or just for your main character and their chief adversary. It doesn’t matter if you’ve answered every question. As you continue to sketch the play, you can go back and answer questions that stumped you the first time.

What you should find is that you suddenly have a more vivid picture of your character’s world and their most driving need. With all this fresh in your mind, the next step is to find your character’s voice. That’s the subject of our next installment.

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