IPhone sends message only to first email address in Address Book

Let's say I want to send an email to Jane.
I have [email protected] and [email protected] in Address Book. Work first, home second.
I select: [email protected] but the message appears to have been sent to [email protected] (?!). Happens all the time.
Why does iPhone do this?
Thank you,
hmcl

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I recently lost my iPod and ive been using find my iPhone to send messages to it, my email instantly tells me that it had been displayed or it suonded off however it doesn't find it's current location. you guys think this app actually works??

i recently lost my 3rd Gen iPod and ive been using find my iPhone to send messages to it, my email then instantly tells me that it had been displayed or it suonded off however it doesn't find the iPod's current location. you guys think this app actually works? i feel like my alerts are just bouncing back at me. please help. Thanks!

... AFAIC Location Services is a joke.
With both devices sitting side by side on my kitchen table, Location Services has NEVER shown the devices to be any where close to each other, and at times Location Services has been as much as a 1/4 of a mile off between the two devices.
Your iPod Touch has no GPS receiver so determining its location relies upon wireless routers whose location is known. Its "location" is actually that of a wireless router. Your iPhone 4 can use GPS, cellular triangulation, and Wi-Fi. One would think GPS would be most accurate but urban areas have a greater density of cells and GPS signals are easily obstructed so cellular triangulation is often more accurate.
Therefore the two devices' locations can be expected to be different. Differences of a quarter mile are easily explained if you understand how location services works: http://support.apple.com/kb/HT1975
Skyhook Wireless (I think Apple uses its own database now): http://www.skyhookwireless.com/howitworks/
Location Services is not a "joke"; its intended use is for basic navigation and for such applications as determining where the nearest restaurant is. It cannot tell you that your iPod is under the couch cushions and that your iPhone is in the car.

When I send messages off-line, they enter in the addressed mailbox with the date and hour which I've clicked "Send later". How could I set up to the real time?

When I send messages off-line, they enter in the addressed mailbox with the date and hour which I've clicked “Send later”. How could I set up to the real time?

What you say about Send Later timestamp is correct.
When you click Send or Send Later a time is set regardless of when you actually sent the Send Later email.
Please voice your vote at this link:
https://bugzilla.mozilla.org/show_bug.cgi?id=560901
You will need to logon/register.

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Hello therealdeal333,
Thank you for participating in the Apple Support Communities.
It sounds like you're only able to send iMessages using your Apple ID (email address) on your iPhone. If you're not able to send iMessages using your phone number, first try signing out of iMessage and FaceTime on your iPhone:
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Go to Settings > FaceTime, tap your Apple ID, then tap Sign Out.
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Sign back in to iMessage and Facetime on your other devices (if necessary.)
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Using FaceTime http://support.apple.com/kb/ht4319http://support.apple.com/kb/ht4319
Troubleshooting FaceTime http://support.apple.com/kb/TS3367http://support.apple.com/kb/TS3367
The Complete Guide to FaceTime + iMessage: Setup, Use, and Troubleshooting
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http://support.apple.com/kb/TS4268http://support.apple.com/kb/TS4268
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http://support.apple.com/kb/HT3529http://support.apple.com/kb/HT3529
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http://www.apple.com/ca/ios/messages/http://www.apple.com/ca/ios/messages/
iOS and OS X: Link your phone number and Apple ID for use with FaceTime and iMessage
http://support.apple.com/kb/HT5538http://support.apple.com/kb/HT5538
How to Set Up & Use iMessage on iPhone, iPad, & iPod touch with iOS
http://osxdaily.com/2011/10/18/set-up-imessage-on-iphone-ipad-ipod-touch-with-io s-5/http://osxdaily.com/2011/10/18/set-up-imessage-on-iphone-ipad-ipod-touch-with-io s-5/
Set Up Alert Sounds
http://www.quepublishing.com/articles/article.aspx?p=1873027&seqNum=3http://www.quepublishing.com/articles/article.aspx?p=1873027&seqNum=3
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http://tinyurl.com/k683gr4http://tinyurl.com/k683gr4
Troubleshooting Messages
http://support.apple.com/kb/TS2755http://support.apple.com/kb/TS2755
Troubleshooting iMessage Issues: Some Useful Tips You Should Try
http://www.igeeksblog.com/troubleshooting-imessage-issues/http://www.igeeksblog.com/troubleshooting-imessage-issues/
Setting Up Multiple iOS Devices for iMessage and Facetime
http://macmost.com/setting-up-multiple-ios-devices-for-messages-and-facetime.htmhttp://macmost.com/setting-up-multiple-ios-devices-for-messages-and-facetime.htm l
FaceTime and iMessage not accepting Apple ID password
http://www.ilounge.com/index.php/articles/comments/facetime-and-imessage-not-acc epting-apple-id-password/http://www.ilounge.com/index.php/articles/comments/facetime-and-imessage-not-acc epting-apple-id-password/
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 Cheers, Tom

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IPhone sends message only to first email address in Address Book

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