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Do you often wonder why Apple's Mail pops up so many email addresses when you create a new message? It's because the program keeps a list of people to whom you've sent email, whether they're in your address book or not.
Even if you've only sent one message to someone, Mail will remember that name in case you want to use it later. Unfortunately, this list can collect misspelled addresses, very old ones, and some that you'll never need again. In Mail, choose Window > Previous Recipients.
Each line shows the person's name, their email address, and the last date you sent something to them. In the example above, lines 1, 2, and 4 (George, Don, and Frank) have little address-book icons at the left. This means they're already in your Address Book. Lines 3, 5, 6, and 7 (Frank, Oliver, blahBlah, and somebody), however, don't have that icon, because they're not in your Address Book.
Lines 6 and 7 (blahBlah and somebody) don't even have the person's name, because they didn't have their names set up properly at their end. All Mail has for them is an email address and no name.
Compare lines 3 and 4 (Frank Morgan). Line 3 is his old email address, balloonist@kansas.net. But he's since moved on to the Land of Oz, and you have his current address in your Address Book. That's what's shown on line 4.
Unfortunately, Mail has remembered Frank's obsolete kansas.net address, and it also knows about the one in your Address Book. But Mail doesn't know which it should use. So when you begin to send a message to "Frank," Mail suggests both of his addresses: the obsolete and the current one. If you inadvertently choose the wrong one, the message will go to kansas.net and bounce back or disappear.
Because these names in the Previous Recipients list will pop up when you address a message, it's good to periodically clean up that list. Mail remembers lots of email addresses, and after a while a lot of those will become obsolete (because people change email addresses.)
Often, the last-used date will provide a clue as to which address is the more recent one to keep.
Having Mail constantly suggest these obsolete email addresses doesn't really make life easier. Let's clean out the deadwood from the list.