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The Free Financial Advisor
The Free Financial Advisor
Catherine Reed

10 First-Date Questions That Practically Guarantee a Bad Ending

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First dates are meant to be fun, lighthearted, and an opportunity to learn whether there’s real chemistry. But sometimes, the wrong first-date questions can turn an evening of possibility into an awkward disaster. The key is to strike a balance between curiosity and respect, without prying too deeply or pushing uncomfortable topics. While it’s natural to want to know more about someone, certain questions almost always lead to a bad ending. Here are ten to avoid if you want your date to feel smooth and enjoyable.

1. “How much money do you make?”

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