Do you think guys will examine your dating boundaries when they think you are interested?

As an example I was going to message him and say "we can meet before or when the event is over," and my friend was like "if you say after - he will suspect something." Like either you want to go on a date with him or you want to sleep with him since it's late when the event is over.

Do guys test you like that?
Do you think guys will examine your dating boundaries when they think you are interested?
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