Devious Questions to Ask
Clever and thought-provoking questions designed to reveal hidden truths, test boundaries, and create engaging conversations that go beyond surface-level interactions.
1What's the most controversial opinion you hold that you're willing to share?
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What's the most controversial opinion you hold that you're willing to share?
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Why this works
Reveals their willingness to share unpopular views and shows you're interested in understanding their deeper beliefs and values.
2If you could get away with one crime, what would it be and why?
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If you could get away with one crime, what would it be and why?
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Why this works
Tests their moral boundaries in a playful way while revealing their values and what they consider acceptable or unacceptable.
3What's something you've never told anyone because you're afraid of how they'd react?
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What's something you've never told anyone because you're afraid of how they'd react?
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Why this works
Creates a safe space for vulnerability while revealing their fears about judgment and their level of trust in the relationship.
4If you could read minds for just one day, whose mind would you choose and why?
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If you could read minds for just one day, whose mind would you choose and why?
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Why this works
Reveals their curiosity about others and shows you're interested in understanding their relationships and what they find mysterious.
5What's the most manipulative thing you've ever done to get what you wanted?
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What's the most manipulative thing you've ever done to get what you wanted?
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Why this works
Tests their honesty about their own behavior while revealing their approach to getting their needs met.
6If you could anonymously ruin someone's reputation, who would it be and why?
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If you could anonymously ruin someone's reputation, who would it be and why?
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Why this works
Reveals their grudges and resentments while showing you're interested in understanding their conflicts and relationships.
7What's the biggest lie you've ever told that you still haven't been caught in?
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What's the biggest lie you've ever told that you still haven't been caught in?
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Why this works
Tests their honesty and reveals their approach to truth-telling while showing you're interested in understanding their secrets.
8If you could have one superpower that would let you get away with anything, what would it be?
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If you could have one superpower that would let you get away with anything, what would it be?
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Why this works
Reveals their desires and fantasies while showing you're interested in understanding what they would do with unlimited power.
9What's the most embarrassing thing you've done that you're actually proud of?
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What's the most embarrassing thing you've done that you're actually proud of?
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Why this works
Reveals their values and what they consider worth being embarrassed about while showing you're interested in understanding their priorities.
10If you could plant a false memory in someone's mind, what would it be and why?
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If you could plant a false memory in someone's mind, what would it be and why?
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Why this works
Tests their approach to manipulation while revealing their desires and what they would want others to believe about them.
11What's the most morally questionable thing you've done that you don't regret?
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What's the most morally questionable thing you've done that you don't regret?
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Why this works
Reveals their moral compass and shows you're interested in understanding their ethical boundaries and decision-making process.
12If you could anonymously expose one person's secret, who would it be and what would you reveal?
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If you could anonymously expose one person's secret, who would it be and what would you reveal?
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Why this works
Reveals their knowledge of others' secrets while showing you're interested in understanding their relationships and what they find scandalous.
13What's the most devious plan you've ever come up with (even if you didn't execute it)?
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What's the most devious plan you've ever come up with (even if you didn't execute it)?
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Why this works
Reveals their creativity and strategic thinking while showing you're interested in understanding their problem-solving approach.
14If you could make one person's life significantly worse without them knowing it was you, would you do it?
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If you could make one person's life significantly worse without them knowing it was you, would you do it?
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Why this works
Tests their willingness to cause harm while revealing their grudges and what they consider justified revenge.
15What's the most unethical thing you've done that you're actually proud of?
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What's the most unethical thing you've done that you're actually proud of?
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Why this works
Reveals their moral flexibility and shows you're interested in understanding their approach to ethical dilemmas.
16If you could anonymously sabotage someone's success, who would it be and why?
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If you could anonymously sabotage someone's success, who would it be and why?
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Why this works
Reveals their competitive nature and shows you're interested in understanding their approach to competition and success.
17What's the most manipulative thing you've ever witnessed someone else do?
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What's the most manipulative thing you've ever witnessed someone else do?
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Why this works
Reveals their awareness of manipulation while showing you're interested in understanding their observations of human behavior.
18If you could have one person's life for a day, who would it be and what would you do?
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If you could have one person's life for a day, who would it be and what would you do?
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Why this works
Reveals their desires and fantasies while showing you're interested in understanding what they would do with someone else's power or position.
19What's the most devious thing you've ever done to get out of trouble?
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What's the most devious thing you've ever done to get out of trouble?
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Why this works
Reveals their problem-solving approach while showing you're interested in understanding their ability to think on their feet.
20If you could anonymously control someone's decisions for a week, who would it be and what would you make them do?
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If you could anonymously control someone's decisions for a week, who would it be and what would you make them do?
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Why this works
Tests their desire for control while revealing their fantasies about power and influence over others.
Best Practices for Devious Questions
Expert tips and techniques for getting the most out of these questions.
Best Practices
Know Your Audience
These questions are designed for people who are comfortable with provocative conversations. Make sure the person is open to this type of interaction before asking.
Create a Safe Space
Establish trust and confidentiality before asking these questions. Make it clear that the conversation is between you and that you won't judge their answers.
Be Prepared for Honest Answers
These questions are designed to reveal truths that people might not normally share. Be ready to handle honest, potentially uncomfortable responses.
Question Sequences
The Truth Revealer Sequence
The Power Fantasy Sequence
Common Pitfalls
Don't Use These in Professional Settings
These questions are designed for personal relationships and social situations. Don't use them in professional or formal contexts where they could be inappropriate.
Avoid Judging Their Answers
These questions are designed to reveal truths that people might not normally share. Don't judge or criticize their responses, as this will shut down the conversation.
Don't Push Too Hard
If someone seems uncomfortable with a question, don't push them to answer. Respect their boundaries and move on to something else.