diff --git a/lib/pry/wrapped_module.rb b/lib/pry/wrapped_module.rb
index 266db281..fc265a39 100644
--- a/lib/pry/wrapped_module.rb
+++ b/lib/pry/wrapped_module.rb
@@ -121,7 +121,11 @@ class Pry
     # Is this a singleton class?
     # @return [Boolean]
     def singleton_class?
-      wrapped != Pry::Method.safe_send(wrapped, :ancestors).first
+      if Pry::Method.safe_send(wrapped, :respond_to?, :singleton_class?)
+        Pry::Method.safe_send(wrapped, :singleton_class?)
+      else
+        wrapped != Pry::Method.safe_send(wrapped, :ancestors).first
+      end
     end
 
     # Is this strictly a module? (does not match classes)
diff --git a/spec/commands/ls_spec.rb b/spec/commands/ls_spec.rb
index d051389c..52385fb1 100644
--- a/spec/commands/ls_spec.rb
+++ b/spec/commands/ls_spec.rb
@@ -161,12 +161,12 @@ describe "ls" do
 
   describe "grep" do
     it "should reduce the number of outputted things" do
-      pry_eval("ls -c").should =~ /ArgumentError/
-      pry_eval("ls -c --grep Run").should.not =~ /ArgumentError/
+      pry_eval("ls -c Object").should =~ /ArgumentError/
+      pry_eval("ls -c Object --grep Run").should.not =~ /ArgumentError/
     end
 
     it "should still output matching things" do
-      pry_eval("ls -c --grep Run").should =~ /RuntimeError/
+      pry_eval("ls -c Object --grep Run").should =~ /RuntimeError/
     end
   end