Outbox messages with Date: None won't send

[s-a-hanks]

I create a msg I hit send it goes to my outbox. Sometimes they go under a
heading of Date: Today other times they go under under a heading that says
Date: None. No matter what I do, it won't send the message under that
heading, and I can't figure out how to move the msg to the Date: Today or
change the date of the msg. There are no flags or restrictions on the msg as
far as delays, etc. Please advise. Thank you.