You can send as many questions as you want, and they don't necessarily need to be conflicting.
You can throw a user bio at it, like "NAME: John Smith, AGE: 71, LOCATION: California" and ask OpenAI:
* Is this user located in the United States?
* Is this user located on the East Coast?
* Is this user located on the West Coast?
* Is this user old enough to vote?
* Is this user old enough to retire?
4 out of 5 of those are all going to resolve Yes, with a far greater than 0.5 rate.
Toss a bunch of freeform text bios at it, and get folks categorized within any number of data-points you're looking for.