So many questions I get, as a dating coach, follow the format of, “How do I ask ____?” That blank might be “for more time together,” “for a date this Friday,” “for a few texts between dates,” “what they’re looking for in the future.” And in all of these cases, I would simple cross off the “how do I ask,” and you’re left with your answer—just ask what’s on your mind!

On Instagram , I posed a query to my followers: What questions do you have regarding planning a date?

The questions ran the gamut, but the general theme was that people seem to overthink. Everything. Now, I’m certainly not judging—we’re all prone to overthinking at one time or another—but as an unbiased third party, I can tell you that things are often much simpler than we make them out to be.

Here are a few of the questio

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