Toss me some numbers and a character (OCs and AU versions welcome) and I'll answer the questions. Multiple characters welcome as well:
1. What is one thing others might find intolerable about them?
2. Do they have any annoying quirks? If so, what are they?
3. Name one or more of their bad habits.
4. Any addictions? (Food, sex, drugs/alcohol, shopping, power/control, etc.)
5. What is one thing they do that can negatively affect their relationship with friends?
6. Their romantic relationships?
7. What is the biggest mistake they’ve ever made?
8. What mistake(s) do they continue to make/have not learned from?
9. Name some of their major physical shortcomings.
10. Some of their emotional shortcomings?
11. What are their intellectual shortcomings?
12. At least one thing that they tend to overreact to.
13. In what ways might they be overly negative and/or pessimistic?
14. Is there anything they are too optimistic about?
15. How might they be ignorant or prejudiced?
16. Do they have any behaviors and/or beliefs that cannot be adequately justified?
17. When would they be too judgmental of someone or something?
18. Are they ever a pushover about something? If so, how?
19. Is there anything they refuse to budge on? What are they stubborn about?
20. What is a self-inflicted misery of theirs? (i.e. something they perpetuate themselves)