It sounds like you are setting up scenarios in your head that T is not part of that are confusing you more. I bet you apologize too often/much? Try not to be so accommodating when you are asking a question; "Are you free 8-9 a.m. on Wednesday?" does not need, "It is okay if you aren't, I'll understand, I can come on Thursday two weeks later or at 5:00 in the afternoon of the 29th. . ."

Ask a single question and wait for the answer to that one before continuing on? Another person does not have your thought processes or problems with scheduling and can only focus on one thing at a time, your initial question and how it affects themselves.