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Here are two ways to start chatting with any of your Yahoo! contacts, or with any of your Windows Live contacts (@hotmail, @msn, @live).

In “Chat & Mobile Text” on the left side of the page, under "Online Contacts", click a contact name.

Example: You might see “2 Online Contacts.” This means two of your contacts are currently online. If you don't see their names, click the triangle to the left to display them. To start chatting, just click a name. A chat window opens in your Yahoo! Mail window. Type your message at the bottom. That’s it—let the conversation begin!
Or, click New Chat. In the new tab that opens, enter the ID of the Yahoo! or Windows Live contact with whom you want to start chatting—and you’re off!