diff --git a/spec/compiler/macro/macro_methods_spec.cr b/spec/compiler/macro/macro_methods_spec.cr
index 4e9b48a4802d..20367bfdbb27 100644
--- a/spec/compiler/macro/macro_methods_spec.cr
+++ b/spec/compiler/macro/macro_methods_spec.cr
@@ -140,6 +140,20 @@ module Crystal
           assert_macro "x", "{{x.class_name}}", [ArrayLiteral.new([Path.new("Foo"), Path.new("Bar")] of ASTNode)] of ASTNode, "\"ArrayLiteral\""
         end
       end
+
+      describe "#nil?" do
+        it "NumberLiteral" do
+          assert_macro "", "{{ 1.nil? }}", [] of ASTNode, "false"
+        end
+
+        it "NilLiteral" do
+          assert_macro "", "{{ nil.nil? }}", [] of ASTNode, "true"
+        end
+
+        it "Nop" do
+          assert_macro "x", "{{ x.nil? }}", [Nop.new] of ASTNode, "true"
+        end
+      end
     end
 
     describe "number methods" do
diff --git a/src/compiler/crystal/macros.cr b/src/compiler/crystal/macros.cr
index bd7609538b0f..7e7956f6ffb0 100644
--- a/src/compiler/crystal/macros.cr
+++ b/src/compiler/crystal/macros.cr
@@ -272,6 +272,10 @@ module Crystal::Macros
     # highlight this node in the error message.
     def raise(message) : NoReturn
     end
+
+    # Returns `true` if this node is a `NilLiteral` or `Nop`.
+    def __crystal_pseudo_nil? : BoolLiteral
+    end
   end
 
   # The empty node. Similar to a `NilLiteral` but its textual representation
diff --git a/src/compiler/crystal/macros/methods.cr b/src/compiler/crystal/macros/methods.cr
index 41604c10d586..aaa66b0f184c 100644
--- a/src/compiler/crystal/macros/methods.cr
+++ b/src/compiler/crystal/macros/methods.cr
@@ -382,6 +382,10 @@ module Crystal
         end
       when "!"
         BoolLiteral.new(!truthy?)
+      when "nil?"
+        interpret_argless_method("nil?", args) do
+          BoolLiteral.new(is_a?(NilLiteral) || is_a?(Nop))
+        end
       else
         raise "undefined macro method '#{class_desc}##{method}'", exception_type: Crystal::UndefinedMacroMethodError
       end