diff --git a/lib/pry/core_extensions.rb b/lib/pry/core_extensions.rb
index d156eb4e..be311965 100644
--- a/lib/pry/core_extensions.rb
+++ b/lib/pry/core_extensions.rb
@@ -87,7 +87,7 @@ class Object
       return class_eval("binding")
     end
 
-    unless respond_to?(:__pry__)
+    unless self.class.method_defined?(:__pry__)
       # The easiest way to check whether an object has a working singleton class
       # is to try and define a method on it. (just checking for the presence of
       # the singleton class gives false positives for `true` and `false`).
diff --git a/spec/commands/cd_spec.rb b/spec/commands/cd_spec.rb
index f4863f34..0b17358b 100644
--- a/spec/commands/cd_spec.rb
+++ b/spec/commands/cd_spec.rb
@@ -250,4 +250,10 @@ describe 'cd' do
   it 'should be able to cd into the Object BasicObject' do
     expect { @t.eval 'cd BasicObject.new' }.to_not raise_error
   end
+
+  # https://github.com/pry/pry/issues/1596
+  it "can cd into objects that redefine #respond_to? to return true" do
+    expect { @t.eval('cd Class.new { def respond_to?(m) true end }.new') }
+      .to_not raise_error
+  end
 end