Some options on the Free Account side: Card Decks --You could build them as cards, one deck for each category, or one deck with every category (as with Trivial Pursuit). If you need to have the answer hidden, that would require having a separate lookup (possibly in a handout) with each question having some unique identifier which can then be cross referenced on the handout. To prevent cheating, you'd have to have the handout inaccessible to players and only accessible to the GM. Rollable Tables -- Similar to card decks, but you don't have to do any graphic editing so it would be faster to setup. Same issues with answers. Handouts -- Probably not the best option as there isn't a way to randomly choose. The only benefit over the above is a GM only area to put answers, though I'm not certain how useful that would be. Pro Level Subscription: API Script -- Nothing can beat this option as a script could be written that would automate the automatic selection of a random question. It could even present the answers as multiple choice and let you pick one then tell you if you're correct. It wouldn't be hard to automate score keeping either.