Do you play poker for fun?

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My boyfriend loves playing poker, usually Texas Holdem. He was playing on Absolute Poker for awhile, but they don't have a lot of games you can play to actually earn money without putting your own money in. On Full-Tilt poker, the new online poker game he's been playing, you can play Tournaments and make cash out of them, without having to pay in your own cash. As a matter of fact, there is a guy on there, that started out with $0, and ended up with over $10,000, without ever putting in any of his own cash. I thought that was pretty awesome. My boyfriend wants to be the next guy to do this, but is getting frusterated because he hasn't been able to win a cash game! I've been wanting to put some money into it for him, just about $50 (it's the minimum deposit), so he can play cash games, even the penny ones, to start earning something. Do you play poker, on or offline, and do you play for cash?