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There are lots of possibilities. Like you had an attachment to large for the receivers mailbox, or the receiver has a mailbox that is full. Most of the time after hours or a day you get a message the mail could not delivered.
Some mail delivery systems put your mail in the spam box of the receiver. If he /she never checks if everything in the spam box is spam, the never discover your mail. And perhaps there could be 100 other reasons.
Outlook was an old program and Microsoft wants you to replace it for the web based version with the same name. Perhaps that version is giving less problems? you also could try Gmail or Yahoo. Most mail is moving towards web based.