You can chat with a hacker in real time in one of the many hacker chat rooms that pop up on nearly every Internet Relay Chat (IRC) network.
To do so, you need a special IRC program, such as mIRC (available at http://www.mirc.co.uk). Once you have an IRC program, you'll need to pick an IRC network to join. Some of the more popular networks are EFnet, DALnet, Undernet, and 2600 net (run by the hacker magazine 2600).
Once you're connected to an IRC network server, you can create a new chat room or join an existing one. While the 2600 network is specifically designed for hackers, you may have to search other networks for chat rooms containing hackers. To find a hacker chat room, look for rooms with names like #2600, #phreak, #carding, #cracks, #anarchy, or any other phrase that sounds hackerish.
Using IRC is a special skill in itself, and many hackers may get upset if you intrude on their chat rooms, so use care when exploring the different networks and chat rooms. With enough patience, you can eventually meet and make friends in the various chat rooms. Soon, you too can become a regular and experienced IRC user and you'll be able to chat with hackers all over the world. To learn more about how to use IRC, pick up Alex Charalabidis' The Book of IRC, published by No Starch Press.