VBA Halp! Sort Columns by date; Insert/add Data Underneath the Cell in Column B

Please see attached for explanation of problemo.excel_example.JPG

Steps:
Sort both columns by date, oldest to new. Add/insert rows of data (command1, command2, command3, etc...) underneath cells in column B of text but not overwriting the existing data.
Please help, I've been working on this for a couple of days now and no luck. Just a lot of head banging and arms in the air!!! Please excuse how I represented my easy question for you guys.