diff --git a/common/src/main/java/me/lucko/luckperms/common/bulkupdate/comparisons/Comparison.java b/common/src/main/java/me/lucko/luckperms/common/bulkupdate/comparisons/Comparison.java
index de005b2bd..23bf7f735 100644
--- a/common/src/main/java/me/lucko/luckperms/common/bulkupdate/comparisons/Comparison.java
+++ b/common/src/main/java/me/lucko/luckperms/common/bulkupdate/comparisons/Comparison.java
@@ -40,18 +40,31 @@ public interface Comparison {
     String getSymbol();
 
     /**
-     * Compares two strings according to this comparisons
-     * behaviour, and returns if they match.
+     * Creates a {@link CompiledExpression} for the given expression
      *
-     * @param str the string
-     * @param expr the expression
-     * @return if the string matches the expression
+     * @param expression the expression
+     * @return the compiled expression
      */
-    boolean matches(String str, String expr);
+    CompiledExpression compile(String expression);
 
     /**
      * Returns the comparison operator in SQL form
      */
     void appendSql(PreparedStatementBuilder builder);
 
+    /**
+     * An instance of {@link Comparison} which is bound to an expression.
+     */
+    interface CompiledExpression {
+
+        /**
+         * Tests the expression against a given string, according to the
+         * rules of the parent {@link Comparison}.
+         *
+         * @param string the string
+         * @return if there was a match
+         */
+        boolean test(String string);
+    }
+
 }
diff --git a/common/src/main/java/me/lucko/luckperms/common/bulkupdate/comparisons/Constraint.java b/common/src/main/java/me/lucko/luckperms/common/bulkupdate/comparisons/Constraint.java
index 4937a6fa1..0ae3f265c 100644
--- a/common/src/main/java/me/lucko/luckperms/common/bulkupdate/comparisons/Constraint.java
+++ b/common/src/main/java/me/lucko/luckperms/common/bulkupdate/comparisons/Constraint.java
@@ -33,15 +33,15 @@ public class Constraint {
         return new Constraint(comparison, expression);
     }
 
-    // the comparison type being used in this query
     private final Comparison comparison;
+    private final String expressionValue;
+    private final Comparison.CompiledExpression compiledExpression;
 
-    // the expression being compared against
-    private final String expression;
 
     private Constraint(Comparison comparison, String expression) {
         this.comparison = comparison;
-        this.expression = expression;
+        this.expressionValue = expression;
+        this.compiledExpression = this.comparison.compile(this.expressionValue);
     }
 
     /**
@@ -51,7 +51,7 @@ public class Constraint {
      * @return true if satisfied
      */
     public boolean eval(String value) {
-        return this.comparison.matches(value, this.expression);
+        return this.compiledExpression.test(value);
     }
 
     public void appendSql(PreparedStatementBuilder builder, String field) {
@@ -59,19 +59,11 @@ public class Constraint {
         builder.append(field + " ");
         this.comparison.appendSql(builder);
         builder.append(" ?");
-        builder.variable(this.expression);
-    }
-
-    public Comparison getComparison() {
-        return this.comparison;
-    }
-
-    public String getExpression() {
-        return this.expression;
+        builder.variable(this.expressionValue);
     }
 
     @Override
     public String toString() {
-        return this.comparison + " " + this.expression;
+        return this.comparison + " " + this.expressionValue;
     }
 }
diff --git a/common/src/main/java/me/lucko/luckperms/common/bulkupdate/comparisons/StandardComparison.java b/common/src/main/java/me/lucko/luckperms/common/bulkupdate/comparisons/StandardComparison.java
index 47d5aadd6..75883341b 100644
--- a/common/src/main/java/me/lucko/luckperms/common/bulkupdate/comparisons/StandardComparison.java
+++ b/common/src/main/java/me/lucko/luckperms/common/bulkupdate/comparisons/StandardComparison.java
@@ -27,6 +27,8 @@ package me.lucko.luckperms.common.bulkupdate.comparisons;
 
 import me.lucko.luckperms.common.bulkupdate.PreparedStatementBuilder;
 
+import java.util.regex.Pattern;
+
 /**
  * An enumeration of standard {@link Comparison}s.
  */
@@ -34,45 +36,31 @@ public enum StandardComparison implements Comparison {
 
     EQUAL("==", "=") {
         @Override
-        public boolean matches(String str, String expr) {
-            return str.equalsIgnoreCase(expr);
+        public CompiledExpression compile(String expression) {
+            return expression::equalsIgnoreCase;
         }
     },
 
     NOT_EQUAL("!=", "!=") {
         @Override
-        public boolean matches(String str, String expr) {
-            return !str.equalsIgnoreCase(expr);
+        public CompiledExpression compile(String expression) {
+            return string -> !expression.equalsIgnoreCase(string);
         }
     },
 
     SIMILAR("~~", "LIKE") {
         @Override
-        public boolean matches(String str, String expr) {
-            // form expression
-            expr = expr.toLowerCase();
-            expr = expr.replace(".", "\\.");
-
-            // convert from SQL LIKE syntax to regex
-            expr = expr.replace("_", ".");
-            expr = expr.replace("%", ".*");
-
-            return str.toLowerCase().matches(expr);
+        public CompiledExpression compile(String expression) {
+            Pattern pattern = StandardComparison.compilePatternForLikeSyntax(expression);
+            return string -> pattern.matcher(string).matches();
         }
     },
 
     NOT_SIMILAR("!~", "NOT LIKE") {
         @Override
-        public boolean matches(String str, String expr) {
-            // form expression
-            expr = expr.toLowerCase();
-            expr = expr.replace(".", "\\.");
-
-            // convert from SQL LIKE syntax to regex
-            expr = expr.replace("_", ".");
-            expr = expr.replace("%", ".*");
-
-            return !str.toLowerCase().matches(expr);
+        public CompiledExpression compile(String expression) {
+            Pattern pattern = StandardComparison.compilePatternForLikeSyntax(expression);
+            return string -> !pattern.matcher(string).matches();
         }
     };
 
@@ -108,4 +96,15 @@ public enum StandardComparison implements Comparison {
         return null;
     }
 
+    static Pattern compilePatternForLikeSyntax(String expression) {
+        expression = expression.toLowerCase();
+        expression = expression.replace(".", "\\.");
+
+        // convert from SQL LIKE syntax to regex
+        expression = expression.replace("_", ".");
+        expression = expression.replace("%", ".*");
+
+        return Pattern.compile(expression);
+    }
+
 }