IP address

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A direct connection with the user when you are using AIM or any messenger will tell you with the command netstat -N unless the service connects to a server as the middle man.

Direct connection as in peer to peer file sharing.

Email- Try looking at the header, it might not show the users IP but will reveal the email server, just not sure I haven't check.
 
Just get the person to make a file transfer, I know on AIM it's a direct connection and you should be able to view the IP address by opening up command prompt and typing netstat -N

I'm not sure if hotmail will let you view the header, though I haven't check.

Not sure in gmail either.

Yahoo, just click "Full Header" below the mail.
 
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