“If distance were involved, would you see us as worth making real plans for?” is a much more serious dating question than it initially sounds. It does not simply ask whether somebody believes in long-distance relationships. It asks whether...
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“What does emotional maturity look like to you in a relationship?” is not the lightest question to drop into a dating conversation, but that may be exactly why it works. It moves past favori...
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Ask people what makes someone attractive and appearance often dominates the first few seconds of the conversation. Yet lasting attraction tends to become more complicated once two people act...
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“Have you ever watched porn with a partner? Would you like to?” is one of those dating questions that sounds provocative but can quickly become a conversation about something much broader: t...
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“What turns you on more: dirty texting or in-person intimacy?” sounds like a playful dating question, but the answer can reveal much more than a preference for phones or face-to-face chemist...
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“Have you ever used sex toys? Which ones?” is a more revealing dating question than it first appears. Between consenting adults, it can open a conversation about curiosity, comfort with sexu...
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“What makes you fall in love during sex?” sounds like a question about physical intimacy, but the most revealing answers are usually emotional. One person may talk about feeling completely t...
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“What’s your sexual guilty pleasure?” is the kind of dating question that can change the temperature of a conversation immediately. It sounds playful and provocative, but its real power is n...
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“Do you like when a woman takes the initiative, or do you prefer to lead?” sounds like a simple either-or question, but it can reveal much more than who makes the first move. Between adults...
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“Have you ever had sex in a public place?” is the kind of question designed to interrupt a predictable dating conversation. It is personal, slightly uncomfortable and difficult to answer wit...
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