These hard would you rather questions skip the silly stuff and ask about real life: careers, family, friendships, money, memory and how you spend your time. Each pair is a genuine tradeoff with no easy answer, which makes them ideal for deeper conversations with close friends, partners or anyone you'd like to get to know better.
Tough questions need a little more space than silly ones. Read one aloud, then give everyone a quiet moment to think before anyone answers. Encourage people to share why they chose their side and what would make them change their mind. It's fine to say a question is too hard to answer, and talking through why can be just as interesting as a final choice.
These questions are best in small groups where people feel comfortable. Listen more than you argue, and avoid judging anyone's answer, since a choice often reflects someone's experiences and values. Try asking how your answer might have been different five or ten years ago. Many players find that the most revealing moment is discovering how differently people they know well see the same dilemma. Mix in a lighter question now and then to keep the mood warm.