Ask the real question.

When someone hears, “What do you have planned for tomorrow?” they are probably thinking “what is it that you are really asking?” Eventually you are going to come out with the real question, you may as well get to it from the very beginning, and avoid the ambiguity and discomfort. –>”I’m thinking that tomorrow, I’d like to go out together. Does that work with your schedule?”
–>”I’m hoping that tomorrow we can tackle [whatever] together. What are your thoughts?”

Reflect on why you have a hard time getting to the real question right up front.

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