build yourself a roster of lighthearted yet thinky questions. some one mine: ”if you could suddenly speak any extra language, what language?” “are you a cowboy, pirate or knight?” (very telling) and my personal favourite, “if you were a weather phenomenon, what would you be?” (i’d be a sun shower, btw)

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keep it light and whimsical. I was on a date a few years back and the person I was with asked me if I believed in luck, she said it was a question she asked everyone and it sparked an interesting discussion- “do you have good/bad luck” “do you know anyone with particularly bad luck“ etc. other questions that might be fun: -are you a cat or a dog (in essence, not preference) -what’s the furthest from home you’ve been? -ever seen a ghost?
May 21, 2025
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I normally think of something spontaneous and weird to ask. It gives the person something fun to respond to and can lead into a good conversation.
6d ago
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Get a laugh plus starts a conversation, something like “so what’s your favourite Spider-Man costume design and why” The dumber the better