Ever since Jarkko "Wiz" Oikarinen created the first Internet Relay Chat client in 1988, chat users have used emoticons to make messages shorter and more fun. Emoticons, sometimes called smileys, are small animations that chat users use to display emotions visually rather than typing a bunch of words. A smiley can express a thought or emotion quickly without having to describe it with text and tends to lead to a more lighthearted message. Smileys are effective visual communications tools for email messages as well, and using them in Outlook is relatively simple.
Download Animated Smiley
Direct your Web browser to a site that offers free animated emoticons for download. Websites such as FreeSmileys.org, MessengerFreak.com and MyEmoticons.com have thousands of free emoticons and smileys you can insert into your Outlook email messages.
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Browse through the various categories of animated emoticons and select one that is appropriate for the message you want to send. Once you select an emoticon, right-click the animated image and click "Save Image As" or "Save Picture As" on the pop-up menu.
Click the "Pictures" link under the "Libraries" header in the new Windows Explorer window. Click the "New Folder" button and replace the "New Folder" name with "Emoticons" or "Smileys." Press the "Enter" key to complete the folder name change. Double-click the new folder to open it.
Click the "Save" button and wait a few seconds for the browser to download the animated image to your computer.
Insert Animated Image in Outlook
Launch Microsoft Outlook on your computer. Click "New E-mail" on the ribbon bar. Click the "To" button and select a recipient from your Outlook Address Book.
Enter a subject in the "Subject" field and text in the message body section of the email window as you normally would. Once you get to the point in the email message text where you want to insert an animated emoticon or smiley, click the "Insert" tab on the Outlook ribbon bar.
Click the "Format Text" tab on the ribbon bar. Click the "HTML" button in the "Format" group.
Click the "Picture" icon in the "Illustrations" group. Outlook opens a new window displaying the Pictures library folders on your computer. Double-click the "Emoticons" or "Smileys" folder you created earlier.
Select the animated image you download earlier and click "Insert." Outlook inserts the image into the message. Enter additional text or images as needed.
Click the "Send" button to send the message. Once the recipient opens the message, the animated smiley is visible.