Ask a question, any question!
1: What does their bedroom look like?
2: Do they have any daily rituals?
3: Do they exercise, and if so, what do they do? How often?
4: What would they do if they needed to make dinner but the kitchen was busy?
5: Cleanliness habits (personal, workspace, etc.)
6: Eating habits and sample daily menu
7: Favorite way to waste time and feelings surrounding wasting time
8: Favorite indulgence and feelings surrounding indulging
9: Makeup?
10: Neuroses? Do they recognize them as such?
11: Intellectual pursuits?
12: Favorite book genre?
13: Sexual Orientation? And, regardless of own orientation, thoughts on sexual orientation in general?
14: Physical abnormalities? (Both visible and not, including injuries/disabilities, long-term illnesses, food-intolerances, etc.)
15: Biggest and smallest short term goal?
16: Biggest and smallest long term goal?
17: Preferred mode of dress and rituals surrounding dress
18: Favorite beverage?
19: What do they think about before falling asleep at night?
20: Childhood illnesses? Any interesting stories behind them?
21: Turn-ons? Turn-offs?
22: Given a blank piece of paper, a pencil, and nothing to do, what would happen?
23: How organized are they? How does this organization/disorganization manifest in their everyday life?
24: Is there one subject of study that they excel at? Or do they even care about intellectual pursuits at all?
25: How do they see themselves 5 years from today?
26: Do they have any plans for the future? Any contingency plans if things don’t workout?
27: What is their biggest regret?
28: Who do they see as their best friend? Their worst enemy?
29: Reaction to sudden extrapersonal disaster (eg The house is on fire! What do they do?)
30: Reaction to sudden intrapersonal disaster (eg close family member suddenly dies)
31: Most prized possession?
32: Thoughts on material possessions in general?
33: Concept of home and family?
34: Thoughts on privacy? (Are they a private person, or are they prone to ‘TMI’?)
35: What activities do they enjoy, but consider to be a waste of time?
36: What makes them feel guilty?
37: Are they more analytical or more emotional in their decision-making?
38: What recharges them when they’re feeling drained?
39: Would you say that they have a superiority-complex? Inferiority-complex? Neither?
40: How misanthropic are they?
41: Hobbies?
42: How far did they get in formal education? What are their views on formal education vs self-education?
43: Religion?
44: Superstitions or views on the occult?
45: Do they express their thoughts through words or deeds?
46: If they were to fall in love, who (or what) is their ideal?
47: How do they express love?
48: If this person were to get into a fist fight, what is their fighting style like?
49: Is this person afraid of dying? Why or why not?