I'm sorry if it's not too viable a solution, but I think the best way to learn to play well is to find someone who is better then you, and play with them. Someone patient is ideal, because you'll want to ask why they did certain things to unravel the depth of strategy involved.

I wouldn't mind trying a few games of chess if you've found a decent freebie version of some kind. I can't promise I'm any better than you though.

Chessmaster 9000 had really GOOD tutorials. I was very impressed with it. I don't know if they've done any more since, but you could probably buy that one for almost nothing and be very happy.

They have a lot of audio commentary from one of the grand masters, and then they have a whole slew of simulated opponents at different skill levels and with different strengths. It really doesn't feel much like you're playing a computer.

Personally, I'd suggest the tutorials before going to get your ass handed to you online.

Stop pawn rushing!

Exactly. Also, go into the game with the agreement that either side can take back any move at any time. It stops the game from being about stupid mistakes, and lets you focus on strategies.

thanks for the suggestions so far.

My problem is that I know absolutely NOTHING about strategy. Nothing. I know how the pieces work, and when I play, I just start moving pieces at random and just react to what the other person does. I don't know anything about openings, midgames, OR endgames

As I said, I suck.

I might look into getting Chessmaster 10th (or 9000? which version is better?) and see if it can tutor me.

The Silman book recommendations above are excellent. He is my favorite Chess writer. I would not start with those books though as you really need to understand the basics first and those books are geared towards intermediate players. If you want to pick up some books, start with Yasser Seirawan's Winning Chess series. They will start you off with the right info and they are very well written.

If you like software, the Chess Mentor series is great, with some good writers/players having contributed. (Silman wrote quite a few of the lessons). Chess computers like Chessmaster can be helpful, but I'd also play games against other people. Redhotpawn (mentioned above) is a great service and the games are correspondence-like, so you can take as long as you want to think about your moves.

After you get the basics down, the single best way to learn chess is to play over master games. Find a player you like, maybe one of the world champions - Kasparov, Fischer, Alekhine, Capablanca - and get a book of his games. Play through them at a board and try to understand what your hero is doing (you won't understand everything, but you will pick up more over time the longer you review them. A great book to help you get started on this technique and see the value in playing over master games is Chernev's Logical Chess Move-by-Move. It is a classic. Good luck!

I have 10th edition and recommend it wholeheartedly. The tutorials are quite deep and you can tweak around the AI to get the feel for different personalities at chess - from very stupid and erratic to very advanced. The last Chessmaster I played was 7000 and 10th edition has really much more to teach. Plus I love the ability to watch historical games and learn from them. Moreover, it can be found cheaply.

As a casual chess player, I can't endorse the Chessmaster series enough. I've owned a couple versions in the past (GBA/6000), but it wasn't until I got my hands on the latest, Chessmaster 10th Ed., that I got a grasp of just how rich the tutorial content is in the series.

There's a section labeled Chessmaster Academy that features dozens and dozens of interactive lessons (likely over a hundred). Everything is covered from the basic rules of gameplay all the way up to advanced theories of Grandmaster strategy. It's conveniently segmented into Chapters that are well organized and take you on a nice learning curve that builds on previous lessons. It's also a nice touch that that finished lessons are check-marked so you never forget where you left off.

As for the content itself, each lesson combines voiced commentary from Josh Waitzkin (Searching For Bobby Fischer) accompanied by animated chess boards that give a visual aid to what is being taught, followed by exercises to reinforce the lesson. Finally, there's an End Chapter quiz (series of "pick the best move/moves"). The voice-overs sync with the animated chess sets and additionally, Josh give personal anecdotes about how what your learning impacted him in his career as a chess champion. It really humanizes the process and keeps it all from feeling too sterile & clinical.

I'm simply floored by the amount of audio commentary in these lessons. It's pretty amazing when you consider that it's basically like having a virtual chess coach giving you dozens of hours of lessons in a very user-friendly environment at the low cost of $20.

Sorry to come off as all hyperbole about the product, but much like the OP, I always had an interest and respect for chess but pretty much sucked and was unsure how to develop my skills. I read a couple books but the format (for me) didn't allow the ideas to stick. Finally discovering the wealth of knowledge in the Chessmaster program and realizing how well presented and user friendly it all was, felt like finding a pot of gold at the end of the rainbow.

Yeah, that's not too hyperbole. [rolls eyes]

(Oh yeah, in case you're wondering, I'm not a plant from the Chessmaster marketing team. )

I, for one, learned the most by playing against other people. The ones that were better than me taught me a whole lot of what not to do, whereas the less talented players allowed me to work out new strategies, while defending without having to think too far in advance.
My attitude with Chess, and Pool especially, is that I really enjoy playing against someone who is better than I am. I find that is the best way to learn.

Oh, and watch out for en passant, it can be a crippling maneuver in certain situations. *cough...queen's pawn rush...cough*

FWIW, Chessmaster : Grandmaster Edition hits the 360 on October 23rd. Not much info on it yet, but it looks like it will have tutorials based on Josh Waitzkin's new book, Chessmaster: The Art of Learning. Looks like it will have the single player game we all love, and multiplayer over Live. It will be interesting to see if this shakes out well. Chess, like poker, seems a better fit on the PC, which will also have this new edition.

If you already know all the rules, then really all you can do to get better is play. You'll learn more from a defeat than a victory, but you'll learn SOMETHING from every game.

The only strategic advice I can give you is try to control the middle and never sacrifice your queen unless you're sure it'll get you a checkmate.

Controlling the middle is pretty sound advice, but sacrificing the queen is often advisable when you think it will lead to positional advantage. Getting too attached to particular material leads to rigidity in thinking and lost opportunity.

Tempo above material.

My System is a classic, but it is pretty advanced for someone who has little knowledge of fundamentals. Personally, I'd pass on Chess Praxis and find a better collection of annotated games by a classical player like Capablanca or Alekhine. Learn classical play - rapid development, occupy/control the center with pieces, etc. before delving into Nimzo's hyper-modern strategies.

man, you guys are so far over my head I have no idea what you're talking about