From Heinz Tschabitscher,
Your Guide to Email.
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Emoticons like :-) or :-O are characteristically only characters. But with Windows Live Hotmail (or MSN Hotmail), you can take smileys one step further and insert graphical emoticons in your messages.

Insert Graphical Smileys in Your Windows Live Hotmail Messages

To insert graphical emoticons in a message with Windows Live Hotmail:

• Make sure you use Internet Explorer or Mozilla Firefox to access Windows Live Hotmail.
• Start a new message.
• Put the insertion mark where you want the emoticon to appear.
• Click on the yellow smiley on the text entry field's toolbar.
• Select the icon you want to insert into your Windows Live Hotmail message from the list that pops up.

Insert Graphical Smileys in Your MSN Hotmail Messages

To put graphical smileys in a message you are composing in MSN Hotmail:

• ›› Step by Step Screenshot Walkthrough

• Click New Message on your MSN Hotmail Today page.
• Make sure the Hotmail rich-text editor is turned on.
• Put the insertion mark where you want the emoticon to appear.
• Click on the yellow smiley on the text entry field's toolbar.
• Select the icon you want to insert into your Hotmail message from the list that pops up.

You can delete a graphical Windows Live Hotmail emoticon like regular text.