Sendit Questions to Ask
Create unforgettable conversations with bold, boundary-pushing questions that reveal hidden truths, challenge assumptions, and create deep connections through honest, unfiltered dialogue.
1What's the most embarrassing thing you've ever done?
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What's the most embarrassing thing you've ever done?
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Why this works
Opens up vulnerability while revealing their capacity for self-awareness and willingness to share personal experiences.
2If you could get away with one crime, what would it be?
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If you could get away with one crime, what would it be?
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Why this works
Explores moral boundaries while revealing their hidden desires and what they consider acceptable or unacceptable behavior.
3What's the worst thing you've ever said about me behind my back?
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What's the worst thing you've ever said about me behind my back?
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Why this works
Forces honest confrontation while revealing their true thoughts about you and how they handle difficult conversations.
4What's your most controversial opinion?
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What's your most controversial opinion?
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Why this works
Reveals their values and beliefs while showing what they consider important enough to defend or argue about.
5If you could read my mind for one day, what would you want to know?
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If you could read my mind for one day, what would you want to know?
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Why this works
Shows their curiosity about you while revealing what secrets or thoughts they think you might be hiding.
6What's the most fucked up thing you've ever thought but never said out loud?
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What's the most fucked up thing you've ever thought but never said out loud?
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Why this works
Creates space for unfiltered honesty while revealing their inner thoughts and what they consider too taboo to share.
7If you could erase one person from everyone's memory, who would it be?
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If you could erase one person from everyone's memory, who would it be?
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Why this works
Explores their relationships and grudges while revealing who they'd rather forget and why.
8What's the most manipulative thing you've ever done?
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What's the most manipulative thing you've ever done?
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Why this works
Opens up discussion about their darker side while revealing their capacity for manipulation and self-awareness.
9If you could get away with cheating on your partner, would you?
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If you could get away with cheating on your partner, would you?
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Why this works
Forces them to confront their relationship values while revealing their thoughts on fidelity and commitment.
10What's the most morally questionable thing you've ever done?
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What's the most morally questionable thing you've ever done?
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Why this works
Opens up honest discussion about ethical boundaries while revealing their personal moral compass and past decisions.
11If you could have dinner with Hitler, what would you ask him?
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If you could have dinner with Hitler, what would you ask him?
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Why this works
Forces them to confront extreme moral dilemmas while revealing their approach to understanding evil and historical figures.
12What's the most fucked up thing you've ever done while drunk?
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What's the most fucked up thing you've ever done while drunk?
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Why this works
Explores their behavior under influence while revealing their capacity for poor decisions and self-control.
13If you had to choose between saving me or a stranger, who would you pick?
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If you had to choose between saving me or a stranger, who would you pick?
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Why this works
Forces them to confront difficult moral choices while revealing how they prioritize relationships and make tough decisions.
14What's the most embarrassing thing you've ever done for money?
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What's the most embarrassing thing you've ever done for money?
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Why this works
Opens up discussion about their boundaries and values while revealing what they'd do for financial gain.
15If you could know one secret about anyone in this room, what would it be?
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If you could know one secret about anyone in this room, what would it be?
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Why this works
Reveals their curiosity about others while showing what information they find most valuable or interesting.
16What's the most fucked up thing you've ever lied about?
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What's the most fucked up thing you've ever lied about?
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Why this works
Opens up discussion about deception while revealing their capacity for dishonesty and what they consider worth lying about.
17If you could get away with one thing without consequences, what would it be?
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If you could get away with one thing without consequences, what would it be?
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Why this works
Explores their desires and boundaries while revealing what they value enough to do if there were no repercussions.
18What's the most fucked up thing you've ever done to get revenge?
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What's the most fucked up thing you've ever done to get revenge?
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Why this works
Opens up discussion about their capacity for retaliation while revealing how they handle conflict and perceived wrongs.
19If you could erase one memory from your mind, what would it be?
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If you could erase one memory from your mind, what would it be?
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Why this works
Reveals their most painful or traumatic experiences while showing what they'd rather forget about their past.
20What's the most fucked up thing you've ever done that you're proud of?
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What's the most fucked up thing you've ever done that you're proud of?
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Why this works
Opens up discussion about their values while revealing what they consider acceptable or even admirable behavior.
Navigating Provocative Conversations
Expert tips and techniques for getting the most out of these questions.
Best Practices
Know Your Audience
Only ask these questions with people who are comfortable with provocative conversation. Gauge their comfort level and respect boundaries.
Create Safe Space
Establish that these are judgment-free conversations. Make it clear that honest answers are valued and won't be held against them.
Be Prepared to Answer
If you're asking provocative questions, be ready to answer them yourself. Reciprocity is important for maintaining trust and openness.
Question Sequences
The Truth Explorer
The Moral Dilemma
Common Pitfalls
Don't Push Too Hard
If someone seems uncomfortable, back off. These questions are meant to be provocative, not harmful or traumatic.
Avoid Judging Answers
Don't judge or shame people for their honest answers. The point is to create open dialogue, not to make people feel bad about themselves.
Don't Use Answers Against Them
Never use their honest answers as ammunition in future arguments or to manipulate them. This destroys trust and openness.