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Let's Get Invasive: Dating Questions
A big red flag is when people get uncomfortable with you asking questions to learn who they are -- especially if they want to date you, have sex with you (unless you're keeping it casual), marry you, take your time, and integrate into your life.
The best part of dating is the learning process, but if you rush into a situation without taking the time to learn who the person is, you might run into some unexpected surprises later on (some of you know what I'm talking about).
Ask all the questions that come to mind (at the right time). The best time to ask is now, not later.