One of the best ways to engage your readers is to discover deep, unexpected dimensions in your characters. For me, these tend to emerge organically as the story develops, but some of the characters that intrigue me most hide their true selves.
A few years ago, I came up with tricks to get to know my characters better. I also have had some success finding aspects of character by referring to Susan Shapiro’s Make Me Worry You’re Not O.K.
In a current work, a key character is unusually taciturn, and I’ve had to move to a tough approach — interrogation. I came up with 50 questions even I would be reluctant to answer because they are rude, invasive, and suggestive of negative characteristics. In other words, they probe the areas that most interest readers.
It’s a brutal “getting to know you” exercise, made more excruciating by my tendency to ask follow-up questions. (My poor characters.) I would not recommend methodically working through all of these questions. Instead, print out the list and check off ten to which you respond viscerally. For me, that means either I would never want to answer the question or I’d really like to hear my character’s answer.
Once you have a solid ten questions, interview your character. I’ve done this both by typing questions and answers and by using dictation. It depends on the character I’m interrogating.
I tend to press for specific answers. Also, I often convert the questions to “Tell me about…” For instance, instead of “What’s the sneakiest thing you’ve ever done?” I’m apt to say, “Tell me about the sneakiest thing you’ve ever done.” Occasionally, when the answer seems superficial, I’ll dig by saying, “Tell me about the three (or ten) sneakiest things you’ve ever done.” Or I’ll just say, “Tell me more.”
On a scale of one to ten in intensity and story value, see if you can get five answers that are eight or higher, even if it means choosing more questions to ask. Feeling generous? Try to turn some questions to the positive. Instead of “When did you first have contempt for an adult?” try “When were you first inspired by someone a lot younger than you?”
If you want to practice before you interview your character, you can take on someone else’s (perhaps from a favorite book or movie). I had some success interrogating a mentor of mine that I know well (in my imagination since he is deceased). Not only did I come out of the exercise with a better sense of the questions, but I had great answers that are likely to be applied to a character some day. If you are really eager, try the questions on yourself.
Ready? Here are the questions I came up with:
1. What’s the sneakiest thing you’ve ever done?
2. What did you think you’d get away with, but didn’t?
3. Why are you so mean?
4. What was you most embarrassing moment?
5. How did you escape someone who wanted to tag along with you or loved you?
6. How were you humiliated?
7. What’s the ugliest thing you ever wore?
8. What’s the most disgusting job you ever had?
9. What’s your guilty pleasure?
10. What’s your worst trauma?
11. What should no one ever ask you to do?
12. What caused you to laugh at someone?
13. What did you do as part of a group that you never would have done by yourself?
14. What’s your biggest secret?
15. What’s your biggest fear?
16. What did you witness that was most discouraging?
17. What did you witness that most upset you?
18. When were you most shaken by the possibility of death?
19. When did you first have contempt for an adult?
20. What’s the most horrendous secret you know about someone?
21. Which lie caused you the most anxiety?
22. What do you wish you could forget?
23. How did you hurt someone you loved in an unforgivable way?
24. What’s the most reckless thing you ever did?
25. How did you endanger an innocent person?
26. Where have you visited hoping you wouldn’t meet anyone you know?
27. What compliment or honor did you receive you didn’t deserve?
28. Who thinks well of you who shouldn’t?
29. Who would you cross the street to avoid talking to?
30. What’s the worst thing you did accidentally?
31. What did you break and never tell anyone about?
32. What’s the worst thing you did where the victim never found out it was you?
33. What did you see that you want to unsee?
34. What did you ask for one too many times?
35. What did you wrongly assume that caused the worst consequences?
36. Who did you treat like crap?
37. What’s the most significant promise you’ve broken?
38. Who do you owe an apology who’ll never get one?
39. Where are you most vulnerable?
40. What task would you avoid at all cost?
41. What’s the dearest thing you’ve lost and will never recover?
42. Which temptation would be irresistible to you?
43. What’s the most extreme thing you’ve ever done?
44. What belief did you hold onto for years that turned out to be false?
45. What torture would make you betray everything?
46. What’s your most loathsome desire?
47. How would you NOT want to be remembered?
48. What do you find most disgusting or perverse that is generally considered acceptable?
49. What was your most unsettling experience?
50. What’s your biggest regret?