user85: 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?

user885: The Alekhine's Defence as black. It's a great practical, attacking weapon:
[FEN ""]
1. e4 Nf6
2. e5 Nd5
3. d4 d6


user924: 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...

user70: The Benko gambit is good if you're playing black.
[FEN ""]
1. d4 Nf6
2. c4 c5
3. d5 b5


user11245: GM Edmar Mednis wrote an excellent book on How to Defeat a Superior Opponent, in which he states that you should not attempt to play to your opponent's weaknesses, but instead play to your strengths.
This means that you should:

Know what playing style suits you
Pick a few openings that lead to games of that kind
Learn the main ideas of those openings, and some key variations (and any traps)

Then he adds:

Find opportunities to create complexity in the position, so that your opponent has a higher chance of making a mistake

There are a few off-the-beaten path openings that will force him out of his book, but they will only give you an advantage if you are also comfortable in the positions to which those openings lead.  If you're both at sea, he's still going to win.
If he's over 2200, you should expect him to have a pet line for each of:

The Sokolsky Opening
Grob's Attack
The Budapest Gambit
The Benko Gambit
The Vienna Game and Gambit
The King's Gambit (this would really be asking for it)
The Blackmar-Diemer Gambit
The Sicilian Wing Gambit (if he plays the Sicilian)
The French Wing Gambit (if he plays the French)
The Trompowsky
The Evans Gambit
The Scotch Game and Gambit
Bird's Opening
The Dutch Defense
Alekhine's Defense
The Scandinavian, including the Icelandic Gambit
The Danish Gambit
The Göring Gambit

but you might catch him with (in order of solidity):

The Two Knights Tango
The Chigorin Defense (QGD)
The Urusov Gambit
The Winckelmann-Riemer Gambit in the French


user65: 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 .


user12: 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.

user94: 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!

85: <p>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?</p>
 885: <p>The <a href="http://en.wikipedia.org/wiki/Alekhine&#39;s_Defence" rel="nofollow noreferrer">Alekhine's Defence</a> as black. It's a great practical, attacking weapon:</p>

<pre><code>[FEN ""]
1. e4 Nf6
2. e5 Nd5
3. d4 d6
</code></pre>
 924: <p>You should play the positions that <em>you</em> 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.</p>

<p>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...</p>
 70: <p>The <a href="http://en.wikipedia.org/wiki/Benko_Gambit" rel="nofollow">Benko gambit</a> is good if you're playing black.</p>

<pre><code>[FEN ""]
1. d4 Nf6
2. c4 c5
3. d5 b5
</code></pre>
 11245: <p>GM Edmar Mednis wrote an excellent book on <a href="http://rads.stackoverflow.com/amzn/click/0945806019" rel="noreferrer"><em>How to Defeat a Superior Opponent</em></a>, in which he states that you should <em>not</em> attempt to play to your opponent's weaknesses, but instead <em>play to your strengths</em>.</p>

<p>This means that you should:</p>

<ul>
<li>Know what playing style suits you</li>
<li>Pick a few openings that lead to games of that kind</li>
<li>Learn the main ideas of those openings, and some key variations (and any traps)</li>
</ul>

<p>Then he adds:</p>

<ul>
<li>Find opportunities to create complexity in the position, so that your opponent has a higher chance of making a mistake</li>
</ul>

<p>There are a few off-the-beaten path openings that will force him out of his book, but they will only give you an advantage if <em>you are also comfortable in the positions to which those openings lead</em>.  If you're both at sea, he's still going to win.</p>

<p>If he's over 2200, you should expect him to have a pet line for each of:</p>

<ul>
<li>The Sokolsky Opening</li>
<li>Grob's Attack</li>
<li>The Budapest Gambit</li>
<li>The Benko Gambit</li>
<li>The Vienna Game and Gambit</li>
<li>The King's Gambit (this would really be asking for it)</li>
<li>The Blackmar-Diemer Gambit</li>
<li>The Sicilian Wing Gambit (if he plays the Sicilian)</li>
<li>The French Wing Gambit (if he plays the French)</li>
<li>The Trompowsky</li>
<li>The Evans Gambit</li>
<li>The Scotch Game and Gambit</li>
<li>Bird's Opening</li>
<li>The Dutch Defense</li>
<li>Alekhine's Defense</li>
<li>The Scandinavian, including the Icelandic Gambit</li>
<li>The Danish Gambit</li>
<li>The Göring Gambit</li>
</ul>

<p>but you might catch him with (in order of solidity):</p>

<ul>
<li>The Two Knights Tango</li>
<li>The Chigorin Defense (QGD)</li>
<li>The Urusov Gambit</li>
<li>The Winckelmann-Riemer Gambit in the French</li>
</ul>
 65: <p>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 &quot;comfort zone&quot; 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.</p>
<p>IM Andrew Martin discusses opening repertoires <a href="http://www.chesspublishing.com/content/repert.htm" rel="noreferrer">here</a>. Based on the above, from his list of opening repertoires I would then suggest:</p>
<blockquote>
<p><strong>For White: Trompowski and Pseudo-Trompowski</strong></p>
<p>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.</p>
<p><strong>For Black: Scandinavian and Slav set-ups</strong></p>
<p>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 .</p>
</blockquote>
 12: <p>Gambits are often a good way to get your opponent out of their comfort zone.  As white, some good gambits include:</p>

<ul>
<li>the Morra Gambit</li>
<li>the Evans Gambit</li>
<li><code>4. Ng5</code> in the Two Knight's Defense (black is sacrificing a pawn here though!)</li>
</ul>

<p>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 <code>d4</code> you can consider playing an early <code>...c5</code> 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.</p>
 94: <p>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.</p>

<p>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:</p>

<ul>
<li>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</li>
<li>Much better theoretical opening knowledge? => use sidelines
and shaky gambits, and pray he doesn't know those ugly refutations
and critical lines</li>
<li>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.</li>
<li>Generally better in every aspect? => play what you like
most and learn from your defeats</li>
</ul>

<p>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 <strong>own</strong> comfort zone makes you stronger - in the long run!</p>
