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Sometimes I end up getting the opportunity to play a friendly game with someone who has played a lot more chess than I have; these games seem more fun and interesting for everyone (and I seem to end up with a better chance of winning) when I can push play away from common positions without incurring a big early disadvantage. Are there openings that I can study to accomplish that more dependably?

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up vote 7 down vote accepted

Gambits are often a good way to get your opponent out of their comfort zone. As white, some good gambits include:

  • the Morra Gambit
  • the Evans Gambit
  • 4. Ng5 in the Two Knight's Defense (black is sacrificing a pawn here though!)

For black, the Sicilian and the King's Indian are good ways to create a double edged game. A line that you know by heart in the Sicilian is probably your best bet. Against d4 you can consider playing an early ...c5 with the Benko Gambit or the Benoni - both of which can lead to an unbalanced game as well. White probably has a fairly good idea of what to do against the KID because it is so common which is why either the Benko or the Benoni can be a nice change of pace.

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I don't agree with this approach. Unsound gambits are about the worst way to play against experienced players: an experienced player will tend to know a gambit's refutation, which will leave you not only playing a stronger opponent but playing one a pawn down as well. Gambits against less experienced players, on the other hand, can be fun and lead to quick wins. – Bryan May 2 '12 at 7:57
The Sicilian against a more experienced player to push him out of his comfort zone?? Best recipe for suicide, IMHO. There are so many lines and sideways, you won't get into your favorite line most of the time, but get beaten to death from memorized lines of your experienced opponent instead. – Ray May 2 '12 at 8:17
@Ray, I would not recommend a main line of the Sicilian, but something forcing, especially the Sveshnikov, would work if you learn enough about it. Then the only issue would be Sicilian sidelines, but that's another whole discussion. – Andrew May 2 '12 at 13:48
@Bryan, the gambits I recommended are all 100% sound. I would not play an unsound gambit against a higher rated player. – Andrew May 2 '12 at 13:48
I highly recommend the Smith Morra Gambit. – xaisoft May 2 '12 at 15:15

You can play a surprising opening, which your more experienced opponent has probably encountered very rarely, like a gambit or a rare sideline. Theoretically-wise you will stand on more even ground then. Even better, since you will play this line often, you will have more practice with it than him, improving the odds even more. But usually such openings are seldom played for a reason, at example because they are unsound, or you have to remember very complicated lines, or they offer less winning chances than competing opening systems. There are so many such opening systems (there are even periodicals dealing exclusively with them) I don't list any of them over others.

Apart from this general thought I would suggest a more detailed approach. Try to understand what the exact nature of the advantages of your opponent (or what your own disadvantages) are and act accordingly:

  • Tactically much better than you? => go for quiet lines with focus on strategic plans, use closed systems with few tactics so you deny him the use of his advantage
  • Much better theoretical opening knowledge? => use sidelines and shaky gambits, and pray he doesn't know those ugly refutations and critical lines
  • Strategically much better? => choose simple systems and learn the ideas behind them thoroughly. You will close the gap soon and know the resulting structures as good as he.
  • Generally better in every aspect? => play what you like most and learn from your defeats

A word of warning, though. For a competing mind this might sound like a clever plan. True, it is fun to spring a surprise weapon at a stronger opponent and gain a victory this way. But, and this is a big BUT, in the long run your goal is probably to become a better player over time, and this means gaining a deeper understanding of all the chess topics. Remember you can't get better at tactics by avoiding them ;) When your opponent leaves his comfort zone, he may play weaker. But leaving your own comfort zone makes you stronger - in the long run!

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You should focus on openings that require thematic or strategic understanding, as opposed to ones that require lots of book-knowledge/theory. Then you will get to positions that you are comfortable in and not have to learn the nuances of sharp and highly-analzyed variations that more experienced players will tend to thrive in. Basically, an experienced player's "comfort zone" is beating a less-experienced player in a theoretical line: they have a risk free way of leaving the opening with an advantage. If you take away that theoretical advantage, I would argue they will be less comfortable facing you.

IM Andrew Martin discusses opening repertoires here. Based on the above, from his list of opening repertoires I would then suggest:

For White: Trompowski and Pseudo-Trompowski

1 d4 Nf6 2 Bg5! And 1 d4 d5 2 Bg5! A must here will be to get hold of as many Julian Hodgson games as possible- he has been carving up Patzer and Grandmaster alike for many, many years. At the heart of this repertoire is the limitation of Black's choices- you are conducting the game on your terms. The positions can be different too- White can opt for Pawn structure play or outright attack depending on how he is feeling.

For Black: Scandinavian and Slav set-ups

Rock solid. As Black vs 1 e4 play the main line BANKER with 1...d5 2 exd5 Qxd5 3 Nc3 Qd8! or 3...Qa5, in both cases following with ...Nf6, ...c6 and ...Bf5! And vs d4 and Flank Openings go for the solid Slav set up with ...c6 and ..d5, aiming for a similar structure. Truly an opening which can be learned in a minimum of time .

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+1 for 'Basically, an experienced player's "comfort zone" is beating a less-experienced player in a theoretical line' – Tony Ennis May 2 '12 at 12:22

The Benko gambit is good if you're playing black.

[FEN ""]
1. d4 Nf6
2. c4 c5
3. d5 b5
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You should play the positions that you play the most and are most comfortable in. Since it is unlikely that those same openings are also the most common for your opponent, you will be relatively more comfortable in them than he is.

The problem with playing a special opening just against experienced players is that you will be just as uncomfortable playing them as they are. That is, unless the experienced player happens to know it, then it's actually only uncomfortable for you...

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The Alekhine's Defence as black. Its a great practical, attacking weapon:

[FEN ""]
1. e4 Nf6
2. e5 Nd5
3. d4 d6
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I don't think I'd recommend this because White has a number of choices Black has to prepare for. Four Pawns, Two Pawns (Jäger), 2. Nc3; I think for this sort of situation you want to limit the opponent's good choices. Bad deviations are OK! – Andrew Lazarus Jan 15 '13 at 0:50

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