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I usually work things out as I go along. I don't know any openings and tend to improvise the opening and the middlegame.

For a player like me, is opposite castling a good or a bad choice? I took a look at the tactics involved in such a game (https://www.chess.com/forum/view/livechess/attack-on-opposite-side-castled-king) and it seems that you need a high tempo to perform well. For someone who never follows a strict plan and improvises, is this an advantage or a disadvantage? Should I castle on the same side and aim for a slower game with less pawn involvement?

Say, for example, my queenside is under attack and the opponent has castled kingside. Castling kingside would reduce pressure and allow me to recollect my thoughts. Castling queenside would allow me to put pressure on the opponent's kingside and form a counterattack quickly. For each of these possibilities, the play style must change, but does castling opposite the opponent actually give me any advantage apart from aggression? Possibly, it would allow my bishops to take a long diagonal against the opposing king, w/hile same-side castling would require more knight action.

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The short answer is that castling long, vs. short or staying in the centre depends on the concrete nature of the position. I would advise against 'castling into it [an attack]', and give this quote from Pillsbury:

Castle because you will or because you must, but not because you can

This means that if I gave a general answer of, say, 'always castle kingside, it's good', then that advice may not apply to many positions, and also goes against your player personality of working things out move-by-move.

If you could post some concrete positions into your question, then the community can comment on if/when castling queenside is appropriate.

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A simple way to think about this: castling to the opposite side of your opponent means that your opponent is also to the opposite side of you.

In many positions, you try and keep some compact pawn structure wherever your king is, so both castling kingside means that using the pawns on g, f, or h exposes your king more to risk. However, Kingside vs. Queenside for either side means that you have those same pieces available to advance and attack. As for tempo, attacking with tempo is, fundamentally, what an attack is. You are able to enact a plan and attack someone before they can attack you.

Which is to say long against someone's short (or vice-versa) is only useful if you believe that you have the time to use that advantage. Otherwise, there isn't really an offensive advantage.

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I'll approach it from a more fundamental way. Steinitz said "One Does Not Simply Walk into Mordor". OK, that was Boromir, but it amounts to the same: One does not simply attack the king. In an equal fight, the defense is bound to win. And note the defense even has 1 king more, and that dude, lest we forget it, has the fighting power of a rook.

Opposite castling thus is advantageous for the attacker in at least two ways:

  1. He can storm with the pawns without exposing his own king. Even jettison them, giving lines for the rooks.
  2. If the defense tries to transfer everything to its king side, I foresee a space problem.

As a consequence, who mates first wins. (Not that this is specific to the situation :-)

As further consequences:

  1. Opposite castling favors a strong attacker. (Or tactician, practically the same)
  2. But opposite castling also favors a strong defender.
  3. Opposite castling disfavors the hesitant and the chicken. (You might have to throw in a lot of unsound looking sacrifices to be first.)
  4. If you are the improvising, no plan guy, I see that as an advantage. Your plan consists of one word: Mate! And ideafulness and seize-the-moment can only help.
  5. Disclaimer: In chess anything is concrete. Thus e.g. "hooks" (a6,h6) favor the opponent who can easier open lines.
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You castle opposite because your king would be safer. Or because you will have an endgame edge due to king position in a game that is not going to be decided by an attack.

Less often you do it to gain a tempo. I have castled long to check the black king on the queens home square after an exchange. That brought the rook to a good file and moved my king to safety and united my rooks.

You might do it to bring another rook to the attack faster without having to move your king out of the way after castling on the side of your attack.

You might do it to facilitate an attack on the other king but that is also not a routine thing to do.

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