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As white I tend to play Queen's Gambit which means bye-bye c pawn. and as Black I play sicilian where the first move you stick your c pawn all the way out there. Then it never seems practical to castle queenside without any pawn protecting my queen there. What openings can I play that tend to lead to queenside castling?
Wrong approach. If you are basing your choice of opening on what side you castle to more often than not, you are approaching this game all wrong.
There are Sicilians where Black castles Queenside. There's are two well-known lines of the QGD where White castles Queenside (Rubinstein, 7.Qc2 instead of 7.Rc1 in the Orthodox, and in the Exchange Variation where White goes for the Kingside Pawn Storm).
But again, basing the opening you play on what side you castle is completely moronic. In many cases, you don't even know which side you are going to. I've played the Caro-Kann, Modern, and Pribyl as Black many times, and in all 3 cases, I have games where I castle Queenside, games where I castle Kingside, and games where I don't castle at all.
Play the position and avoid all pre-meditation. The only move that can be safely pre-meditated is White's 1st move. Period!
So what is the right way to decide between sound openings? I figured it was just a matter of personal preference. It’s not like I’m planning on castling queenside even when it doesn’t make sense according to the position. I just want to better understand when it makes sense to castle queenside, and then play openings that lead to that position.
Normally my preference would be to play openings that lead to positions where I feel the most comfortable, but I’m new enough that I don’t know which positions I might feel the most comfortable in. That’s why I’m looking to experiment now.
When experimenting with openings to determine which ones you are most comfortable with, it should never be based on which side you castle to. It should primarily be based on the center. Questions to ask yourself would include:
Do you prefer to have a space advantage, dealing with weaknesses that come as a result of that? For example, as White, if you build the big center, you have to watch out for overextending. As Black, most lines that lead to an equality or advantage in amount of space, like the Stonewall Dutch, involve other weaknesses, like in the Stonewall Dutch, you have the Bad Bishop, the hole on e5, and the backwards pawn on e6.
Do you prefer to be free of weaknesses, and as a result, you deal with the possibility of being severly cramped. Defenses like the Orthodox QGD and Slav fall in this category.
Do you prefer to allow your opponent a free hand at the center, and then you chip away at it, going on the theory that your opponent will overextend. Openings like the Grunfeld fall in this category.
There are 3 schools of chess. All pertain to your approach in the center:
Classical - You control the center with your pawns. Pieces still come into play to prevent expansion, but typically you will have what is known as a strong point, typically occupied by a central pawn. Openings that follow the Classical School of Chess are the main line closed Ruy Lopez (Black's strongpoint is e5), the QGD/Slav/Semi-Slav (Black's strongpoint is typically d5, and even in the case of the Slav, where dxc4 is played, d5 isn't "occupied" by a Black pawn any more, but Black still controls d5 as a strong point), etc.
Modern - The Modern School of chess entails you controlling and occupying the center with pieces. Typically these positions are wide open, and the better centralized pieces steal the show. This is the least popular of the 3 approaches, and probably the best opening to describe this approach would be the Scotch Game.
Hypermodern - The Hypermodern School of chess believes in allowing the opposing side to own the center, and then you chip away at it, going on the basis of overextending. To be deemed a hypermodern opening, typically your central pawns are rarely advanced past the 3rd rank until very late in the game, at least 1 Bishop must be Fianchettoed, and very few pieces are ever traded early. Some deem the Hypermodern School as those that go for "Routine Play". If you think about it, may hypermodern openings, like the Reti, English, King's Indian Defense, etc, typically involve the same moves over and over and over again.
I tend to do best with the Classical or Hypermodern train of thought. The Modern School of chess isn't my cup of tea. If I'm going to occupy the center, I'm going to occupy it with my pawns. Otherwise, I'll let you overextend and chip away.
In queens gambit declined one option is to play the exchange and castle queenside regardless of whether the knight is on f3. The other is to play mainlines up to Qc2/Qb3. You meet h6 with Bxf6 and castle long. This can be tricky against Tartakower (Black plays b6) because Black has some gambit ideas that White shouldn't take. 4.Bg5 Nbd7 is tricky because after c6 and Qa5 this plan doesn't work anymore.
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