How to know the signs of when to attack?

Hi everyone. I have been wondering about this for a long time. In most of my games, I often launch an attack against a king at the wrong time. Observe:

So that is the full game. I added my thoughts, so you can understand why I did some of the stupid moves I did. How do I know the markings of when an attack should be executed. And how should I best debate the pros and cons of a move, such as when I castled Queen side.

Thanks for all input and any criticism that teaches me something is appreciated.

Cheers!

To answer your first question about opposite side castling.

Let’s take a look at when it makes sense to castle opposite sides and when it doesn't.

You should castle on the opposite side when at least one of the following factors is true:

1. When you are up in development and your opponent has already castled, you should consider castling in the opposite side. That way you will have a clear game plan and will also be able to capitalize on your development advantage.
2. When you have a damaged pawn structure (doubled paws, missing pawns, far advanced pawns, etc.) on one of the sides you should consider castling on the other side.
3. When opponent’s pieces are especially active on one side of the board, it is usually best to castle on the opposite side.
4. If you want to complicate the game you may consider this option. That may be true if you must play for a win due to a tournament situation, when the draw is not enough. Also that maybe done when you're playing against a stronger opponent, who is much better in simple/technical positions. That maybe your best bet.

You should not castle on the opposite sides when at least one of the following factors in true:

1. When you are behind in development and you need extra time to develop your pieces, it is usually not a good idea to give your opponent a straight forward way of launching an attack.
2. When the opponent’s pawns are advanced towards the side you’re about to castle, it is not a good idea to castle there (especially if the opponent’s king is castled on the opposite side). It will just give him a positional edge in the attack.
3. When there are open/semi-open files in-front of the side you’re about to castle, you should probably reconsider your decision to castle there (especially if your opponent has castled on the other side). That will give him more attacking possibilities, such as rook lifts, various sacrifices, doubling of pieces on the file, etc.
4. If you playing against a weaker opponent you may want to avoid castling opposite sides, in order to avoid sharp game and keep everything under control.

Note: These are general rules, not laws, meaning that there are always exceptions to them. When you’re making a decision what side to castle you should always take your time and evaluate all “pros” and “cons” and base your decision upon your own analysis. This is a very important decision. It pretty much dictates which way the game will continue. Take your time and think twice.

As far as knowing where to play?

Middlegame Planning:

1. Expand your position:

a. Gain more space.

b. Improve the position of your pieces.

2. Decide on what side of the board to play.

a. Queenside: a-c files.

b. Center: d-e files.

c. Kingside: f-h files.

Compare, space, material, and weakness(es)

Play where you have the advantage.

3. DO NOT HURRY.  Regroup your pieces, and be patient.

Seemed fine to me too.  Maybe you didn't like Queenside castling?

One principle that I had to learn the hard way (OTB) was this:

You don't attack in order to gain the advantage. You gain the advantage by maneuver.

Once you have secured an advantageous position (by maneuver!), THEN you should attack, in order to convert your already-existing advantage into a more convenient form... to convert an advantage in development into a mate or win of a piece, for example.

You are both correct in saying that attack was fine. I was mainly talking about how I should calculate deeper attacks. My question about queen side castling was already answered, so I'll talk about what I mean by better attacks.

That game I put up wan't really a great example of a mistimed attack. I am mainly talking about lines in the sicilian defence dragon variation where black castles king side and white castles queen side. At this point, I usually start pushing the a and b pawns to launch an attack, while white often does the same on my king. Usually I find that after my pawns approach the king, and I have multiple pieces aimed at the king, I can never see any further way to progress, while white manages to break open my king side due to my pieces not being there to defend. 

Just before this point, I generally consider sacrificing a piece, but I am not good enough to calculate far enough to know whether my attack will succeed. When you reach this kind of position, what is the best indicator of how you should go ahead and execute the attack? And are there any good ways to calculate lines like that faster, because I am not good at calculating.

My above questions apply to any position where I have an attack against the king, not just the sicilian example. Thanks for any help.

No offense, but I trust blueemu and his answer more. His answer seems more logical and he is talking about OTB games, meaning long games where the opponent has much time to think and react and come up with proper answers to your wishful attacks. In blitz games, what you say can easily work, but in long games you need to have some kind of advantage in order to convert. You can see that in your own games, where you seem to play better on faster controls, where what you described applies.

Why didn't you play 28...Nxe4+ where you have a winning advantage?

The decision to attack generally revolves around gaining local material superiority.  In Fred Wilson's excellent Simple Attacking Plans, he says point all of your pieces at your opponent's king. Here's a favorite game of mine where I blundered early, went down a Rook and realized my only chance was to launch an all out attack on my opponent's King before he was able to organize his pieces: