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Go to Preferences | Sharing | Sharing books by eMail, add your friend as an eMail recipient with their eMail address and then MOBI as the format. Ensure that the rest of the setup is correct as well (ie your eMail address etc).
Once all that is done, select one of the books you want to send to your friend, right click on it, select connect/share and then eMail to and their eMail address. Calibre will ask you whether you want to convert the book to MOBI; say yes, and then the book will be mailed to them.
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