diff --git a/lib/liquid/expression.rb b/lib/liquid/expression.rb
index c36583c1..29cfc09d 100644
--- a/lib/liquid/expression.rb
+++ b/lib/liquid/expression.rb
@@ -26,31 +26,29 @@ module Liquid
     RANGES_REGEX = /\A\(\s*(?>(\S+)\s*\.\.)\s*(\S+)\s*\)\z/
     INTEGER_REGEX = /\A(-?\d+)\z/
     FLOAT_REGEX = /\A(-?\d+)\.\d+\z/
+    QUOTED_STRING = /\A#{QuotedString}\z/
 
     class << self
-      def parse(markup, ss = StringScanner.new(""), cache = nil, logical_expression = false)
+      def parse(markup, ss = StringScanner.new(""), cache = nil)
         return unless markup
 
         markup = markup.strip # markup can be a frozen string
 
-        if (markup.start_with?('"') && markup.end_with?('"')) ||
-          (markup.start_with?("'") && markup.end_with?("'"))
-          return markup[1..-2]
-        elsif LITERALS.key?(markup)
-          return LITERALS[markup]
-        end
+        return markup[1..-2] if QUOTED_STRING.match?(markup)
+
+        return LITERALS[markup] if LITERALS.key?(markup)
 
         # Cache only exists during parsing
         if cache
           return cache[markup] if cache.key?(markup)
 
-          cache[markup] = inner_parse(markup, ss, cache, logical_expression).freeze
+          cache[markup] = inner_parse(markup, ss, cache).freeze
         else
-          inner_parse(markup, ss, nil, logical_expression).freeze
+          inner_parse(markup, ss, nil).freeze
         end
       end
 
-      def inner_parse(markup, ss, cache, logical_expression = false)
+      def inner_parse(markup, ss, cache)
         return LogicalExpression.parse(markup, ss, cache)    if LogicalExpression.logical?(markup)
         return ComparisonExpression.parse(markup, ss, cache) if ComparisonExpression.comparison?(markup)
 
@@ -66,7 +64,7 @@ module Liquid
         if (num = parse_number(markup, ss))
           num
         else
-          VariableLookup.parse(markup, ss, cache, logical_expression)
+          VariableLookup.parse(markup, ss, cache)
         end
       end
 
diff --git a/lib/liquid/expression/logical_expression.rb b/lib/liquid/expression/logical_expression.rb
index 47bd6f5b..9fcfa382 100644
--- a/lib/liquid/expression/logical_expression.rb
+++ b/lib/liquid/expression/logical_expression.rb
@@ -19,34 +19,20 @@ module Liquid
         def parse(markup, ss, cache)
           expressions = markup.scan(EXPRESSIONS_AND_OPERATORS)
 
-          last_expr = expressions.pop
-
-          condition = if ComparisonExpression.comparison?(last_expr)
-            ComparisonExpression.parse(last_expr, ss, cache)
-          elsif logical?(last_expr)
-            LogicalExpression.parse(last_expr, ss, cache)
-          else
-            Condition.new(Expression.parse(last_expr, ss, cache, true), nil, nil)
-          end
+          expression = expressions.pop
+          condition  = parse_condition(expression, ss, cache)
 
           until expressions.empty?
             operator = expressions.pop.to_s.strip
+
             next unless boolean_operator?(operator)
 
-            expr = expressions.pop.to_s.strip
+            expression    = expressions.pop.to_s.strip
+            new_condition = parse_condition(expression, ss, cache)
 
-            new_condition = if ComparisonExpression.comparison?(expr)
-              ComparisonExpression.parse(expr, ss, cache)
-            elsif logical?(expr)
-              LogicalExpression.parse(expr, ss, cache)
-            else
-              Condition.new(Expression.parse(expr, ss, cache, true), nil, nil)
-            end
-
-            if operator == 'and'
-              new_condition.and(condition)
-            else # operator == 'or'
-              new_condition.or(condition)
+            case operator
+            when 'and' then new_condition.and(condition)
+            when 'or'  then new_condition.or(condition)
             end
 
             condition = new_condition
@@ -54,6 +40,19 @@ module Liquid
 
           condition
         end
+
+        private
+
+        def parse_condition(expr, ss, cache)
+          return ComparisonExpression.parse(expr, ss, cache) if comparison?(expr)
+          return LogicalExpression.parse(expr, ss, cache)    if logical?(expr)
+
+          Condition.new(Expression.parse(expr, ss, cache), nil, nil)
+        end
+
+        def comparison?(...)
+          ComparisonExpression.comparison?(...)
+        end
       end
     end
   end
diff --git a/lib/liquid/variable_lookup.rb b/lib/liquid/variable_lookup.rb
index e4167f2b..340c0b66 100644
--- a/lib/liquid/variable_lookup.rb
+++ b/lib/liquid/variable_lookup.rb
@@ -5,14 +5,12 @@ module Liquid
     COMMAND_METHODS = ['size', 'first', 'last'].freeze
 
     attr_reader :name, :lookups
-    attr_accessor :logical_expression
 
-    def self.parse(markup, string_scanner = StringScanner.new(""), cache = nil, logical_expression = false)
-      new(markup, string_scanner, cache, logical_expression)
+    def self.parse(markup, string_scanner = StringScanner.new(""), cache = nil)
+      new(markup, string_scanner, cache)
     end
 
-    def initialize(markup, string_scanner = StringScanner.new(""), cache = nil, logical_expression = false)
-      @logical_expression = logical_expression
+    def initialize(markup, string_scanner = StringScanner.new(""), cache = nil)
       lookups = markup.scan(VariableParser)
 
       name = lookups.shift
@@ -47,17 +45,9 @@ module Liquid
     end
 
     def evaluate(context)
-      puts "variable_lookup #evaluate #{@name} #{logical_expression?}"
       name   = context.evaluate(@name)
       object = context.find_variable(name)
 
-      # When evaluating a logical expression, this variable lookup is part of a chain of conditions
-      # If the variable lookup returns nil, we must use the falsey value of the variable lookup
-      # rather than nil which is reserved for the usecase of rendering nothing.
-      if logical_expression? && object.nil?
-        return false
-      end
-
       @lookups.each_index do |i|
         key = context.evaluate(@lookups[i])
 
@@ -99,10 +89,6 @@ module Liquid
       self.class == other.class && state == other.state
     end
 
-    def logical_expression?
-      @logical_expression
-    end
-
     protected
 
     def state
diff --git a/test/unit/boolean_unit_test.rb b/test/unit/boolean_unit_test.rb
index 84c29fea..383217e8 100644
--- a/test/unit/boolean_unit_test.rb
+++ b/test/unit/boolean_unit_test.rb
@@ -95,10 +95,58 @@ class BooleanUnitTest < Minitest::Test
     assert_equal("true",  template.render("media_position" => 2))
   end
 
-  def test_equality_operators
-    assert_parity("1 == 1", "true")
-    assert_parity("1 != 2", "true")
-    assert_parity_todo!("'hello' == 'hello'", "true")
+  def test_equality_operators_with_integer_literals
+    assert_expression("1", "1")
+    assert_expression("1 == 1", "true")
+    assert_expression("1 != 1", "false")
+    assert_expression("1 == 2", "false")
+    assert_expression("1 != 2", "true")
+  end
+
+  def test_equality_operators_with_stirng_literals
+    assert_expression("'hello'", "hello")
+    assert_expression("'hello' == 'hello'", "true")
+    assert_expression("'hello' != 'hello'", "false")
+    assert_expression("'hello' == 'world'", "false")
+    assert_expression("'hello' != 'world'", "true")
+  end
+
+  def test_equality_operators_with_float_literals
+    assert_expression("1.5", "1.5")
+    assert_expression("1.5 == 1.5", "true")
+    assert_expression("1.5 != 1.5", "false")
+    assert_expression("1.5 == 2.5", "false")
+    assert_expression("1.5 != 2.5", "true")
+  end
+
+  def test_equality_operators_with_nil_literals
+    assert_expression("nil", "")
+    assert_expression("nil == nil", "true")
+    assert_expression("nil != nil", "false")
+    assert_expression("null == nil", "true")
+    assert_expression("null != nil", "false")
+  end
+
+  def test_equality_operators_with_boolean_literals
+    assert_expression("true", "true")
+    assert_expression("false", "false")
+    assert_expression("true == true", "true")
+    assert_expression("true != true", "false")
+    assert_expression("false == false", "true")
+    assert_expression("false != false", "false")
+    assert_expression("true == false", "false")
+    assert_expression("true != false", "true")
+  end
+
+  def test_equality_operators_with_empty_literals
+    assert_expression("empty", "")
+    assert_expression("empty == ''", "true")
+    assert_expression("empty == empty", "true")
+    assert_expression("empty != empty", "false")
+    assert_expression("blank == blank", "true")
+    assert_expression("blank != blank", "false")
+    assert_expression("empty == blank", "true")
+    assert_expression("empty != blank", "false")
   end
 
   def test_nil_renders_as_empty_string
@@ -122,18 +170,41 @@ class BooleanUnitTest < Minitest::Test
   end
 
   def test_nil_variable_in_and_expression
-    assert_parity("x and true", "false", { "x" => nil })
-    assert_parity("true and x", "false", { "x" => nil })
+    assert_condition("x and true", "false", { "x" => nil })
+    assert_condition("true and x", "false", { "x" => nil })
+
+    assert_expression("x and true", "",     { "x" => nil })
+    assert_expression("true and x", "",     { "x" => nil })
   end
 
   def test_boolean_variable_in_and_expression
     assert_parity("true and x", "false", { "x" => false })
     assert_parity("x and true", "false", { "x" => false })
+
+    assert_parity("true and x", "true",  { "x" => true })
+    assert_parity("x and true", "true",  { "x" => true })
+
+    assert_parity("true or x", "true",   { "x" => false })
+    assert_parity("x or true", "true",   { "x" => false })
+
+    assert_parity("true or x", "true",   { "x" => true })
+    assert_parity("x or true", "true",   { "x" => true })
   end
 
   def test_multi_variable_boolean_nil_and_expression
-    assert_parity("x and y", "false", { "x" => nil, "y" => true })
-    assert_parity("y and x", "false", { "x" => true, "y" => nil })
+    assert_condition("x and y", "false", { "x" => nil, "y" => true })
+    assert_condition("y and x", "false", { "x" => true, "y" => nil })
+
+    assert_expression("x and y", "",     { "x" => nil, "y" => true })
+    assert_expression("y and x", "",     { "x" => true, "y" => nil })
+  end
+
+  def test_multi_truthy_variables_and_expressions
+    assert_condition("x or y", "true",   { "x" => nil, "y" => "hello" })
+    assert_condition("y or x", "true",   { "x" => "hello", "y" => nil })
+
+    assert_expression("x or y", "hello", { "x" => nil, "y" => "hello" })
+    assert_expression("y or x", "hello", { "x" => "hello", "y" => nil })
   end
 
   def test_multi_variable_boolean_nil_or_expression