diff --git a/index.js b/index.js
index 4c66afa..0329aa3 100644
--- a/index.js
+++ b/index.js
@@ -63,8 +63,16 @@ exports.string = function(val){
  *  Dollar-Quoted String Constants
  */
 
-var randomTags = [ 'a', 'b', 'c', 'd', 'e', 'f', 'g', 'h', 'i', 'g', 'j', 'k',
-  'l', 'm', 'n', 'o', 'p', 'q', 'r', 's', 't'];
+var randomTags = [
+  // Upper case alpha sans vowels
+  'B', 'C', 'D', 'F', 'G', 'H', 'J', 'K', 'L', 'M',
+  'N', 'P', 'Q', 'R', 'S', 'T', 'V', 'W', 'X', 'Z',
+  // Lower case alpha sans vowels
+  'b', 'c', 'd', 'f', 'g', 'h', 'j', 'k', 'l', 'm',
+  'n', 'p', 'q', 'r', 's', 't', 'v', 'w', 'x', 'z',
+  // Numeric two through nine
+  '2', '3', '4', '5', '6', '7', '8', '9',
+];
 
 /**
  * produces a random number from a given range
@@ -84,6 +92,9 @@ function random(start, end) {
  * Format as dollar quoted string.
  * see: http://www.postgresql.org/docs/8.3/interactive/sql-syntax-lexical.html#SQL-SYNTAX-DOLLAR-QUOTING
  *
+ * Initially tries to use a tagless $$ as the quote wrapper. If it appears in the string to be quoted, then
+ * successively longer random tags are chosen until one is found that is not contained within the string.
+ *
  * @param {Mixed} val
  * @return {String}
  * @api public
@@ -91,8 +102,20 @@ function random(start, end) {
 
 exports.dollarQuotedString = function(val) {
   if (val === undefined || val === null || val === '') return '';
-  var randomTag = '$'+ randomTags[ random(0, randomTags.length) ] +'$';
-  return randomTag + val + randomTag;
+  // Ensure val is coerced to a string
+  val = '' + val;
+  // Start with an empty tag: $$
+  var tag = '';
+  while (true) {
+    var dollarQuote = '$'+ tag + '$';
+    // Check if val contains our selected dollar quote tag
+    if (val.indexOf(dollarQuote) < 0) {
+      // Not contained so dollarQuote is safe to use
+      return dollarQuote + val + dollarQuote;
+    }
+    // Tag was contained within val so add random character to it
+    tag += randomTags[ random(0, randomTags.length) ];
+  }
 }
 
 /**
diff --git a/test/index.js b/test/index.js
index 10baaa8..a5c6b58 100644
--- a/test/index.js
+++ b/test/index.js
@@ -42,7 +42,7 @@ describe('escape(fmt, ...)', function(){
   describe('%Q', function(){
     it('should format as a dollar quoted string', function(){
       escape('%Q', "Tobi's")
-        .should.match(/\$[a-z]{1}\$Tobi's\$[a-z]\$/);
+        .should.match("$$Tobi's$$");
     })
   })
 })
@@ -59,12 +59,29 @@ describe('escape.string(val)', function(){
 describe('escape.dollarQuotedString(val)', function() {
   it('should coerce to a dollar quoted string', function(){
     escape.dollarQuotedString().should.equal('');
-    escape.dollarQuotedString(0).should.match(/\$[a-z]{1}\$0\$[a-z]\$/);
-    escape.dollarQuotedString(15).should.match(/\$[a-z]{1}\$15\$[a-z]\$/);
-    escape.dollarQuotedString('something').should.match(/\$[a-z]{1}\$something\$[a-z]\$/);
+    escape.dollarQuotedString(0).should.equal('$$0$$');
+    escape.dollarQuotedString(15).should.equal('$$15$$');
+    escape.dollarQuotedString('something').should.equal('$$something$$');
   })
 })
 
+describe('escape.dollarQuotedString(val)', function() {
+  it('should handle quoting strings with dollar quotes in them', function(){
+    escape.dollarQuotedString('$$').should.match(/\$[a-zA-Z0-9]+\$\$\$\$[a-zA-Z0-9]+\$/);
+  })
+
+  it('should handle dollar quotes in the string being escaped without resorting to luck', function(){
+    var sql = 'SELECT $a$test$a$';
+    // The only occurrences of $a$ in the string should be from the string itself.
+    // The repeated test from the for loop is to catch $a$ randomly being chosen as the tag.
+    for(var i=0;i<1000;i++) {
+      var escapedSql = escape.dollarQuotedString(sql);
+      var count = escapedSql.match(/\$a\$/g).length;
+      assert(count === 2);
+    }
+  });
+})
+
 describe('escape.ident(val)', function(){
   it('should quote when necessary', function(){
     escape.ident('foo').should.equal('foo');