diff --git a/modules/openapi-generator/src/main/resources/python-experimental/schemas.handlebars b/modules/openapi-generator/src/main/resources/python-experimental/schemas.handlebars
index 192afe61717e..5f51148b94f1 100644
--- a/modules/openapi-generator/src/main/resources/python-experimental/schemas.handlebars
+++ b/modules/openapi-generator/src/main/resources/python-experimental/schemas.handlebars
@@ -2,9 +2,8 @@
 
 {{>partial_header}}
 
-from collections import defaultdict, abc
+from collections import defaultdict
 from datetime import date, datetime, timedelta  # noqa: F401
-from dataclasses import dataclass
 import functools
 import decimal
 import io
@@ -470,7 +469,6 @@ class Singleton:
     Enums and singletons are the same
     The same instance is returned for a given key of (cls, arg)
     """
-    # TODO use bidict to store this so boolean enums can move through it in reverse to get their own arg value?
     _instances = {}
 
     def __new__(cls, *args, **kwargs):
@@ -488,7 +486,13 @@ class Singleton:
         return cls._instances[key]
 
     def __repr__(self):
-        return '({}, {})'.format(self.__class__.__name__, self)
+        if isinstance(self, NoneClass):
+            return f'<{self.__class__.__name__}: None>'
+        elif isinstance(self, BoolClass):
+            if (self.__class__, True) in self._instances:
+                return f'<{self.__class__.__name__}: True>'
+            return f'<{self.__class__.__name__}: False>'
+        return f'<{self.__class__.__name__}: {super().__repr__()}>'
 
 
 class NoneClass(Singleton):
diff --git a/samples/openapi3/client/petstore/python-experimental/petstore_api/schemas.py b/samples/openapi3/client/petstore/python-experimental/petstore_api/schemas.py
index 47819dcbca86..0c1dbcb632b1 100644
--- a/samples/openapi3/client/petstore/python-experimental/petstore_api/schemas.py
+++ b/samples/openapi3/client/petstore/python-experimental/petstore_api/schemas.py
@@ -9,9 +9,8 @@
     Generated by: https://openapi-generator.tech
 """
 
-from collections import defaultdict, abc
+from collections import defaultdict
 from datetime import date, datetime, timedelta  # noqa: F401
-from dataclasses import dataclass
 import functools
 import decimal
 import io
@@ -477,7 +476,6 @@ class Singleton:
     Enums and singletons are the same
     The same instance is returned for a given key of (cls, arg)
     """
-    # TODO use bidict to store this so boolean enums can move through it in reverse to get their own arg value?
     _instances = {}
 
     def __new__(cls, *args, **kwargs):
@@ -495,7 +493,13 @@ def __new__(cls, *args, **kwargs):
         return cls._instances[key]
 
     def __repr__(self):
-        return '({}, {})'.format(self.__class__.__name__, self)
+        if isinstance(self, NoneClass):
+            return f'<{self.__class__.__name__}: None>'
+        elif isinstance(self, BoolClass):
+            if (self.__class__, True) in self._instances:
+                return f'<{self.__class__.__name__}: True>'
+            return f'<{self.__class__.__name__}: False>'
+        return f'<{self.__class__.__name__}: {super().__repr__()}>'
 
 
 class NoneClass(Singleton):
diff --git a/samples/openapi3/client/petstore/python-experimental/tests_manual/test_boolean_enum.py b/samples/openapi3/client/petstore/python-experimental/tests_manual/test_boolean_enum.py
index b2080043ce25..36827aa2a9ab 100644
--- a/samples/openapi3/client/petstore/python-experimental/tests_manual/test_boolean_enum.py
+++ b/samples/openapi3/client/petstore/python-experimental/tests_manual/test_boolean_enum.py
@@ -10,7 +10,6 @@
 """
 
 
-import sys
 import unittest
 
 import petstore_api
@@ -28,9 +27,10 @@ def tearDown(self):
 
     def test_BooleanEnum(self):
         """Test BooleanEnum"""
-        # FIXME: construct object with mandatory attributes with example values
         model = BooleanEnum(True)
-        model is BooleanEnum.TRUE
+        # TODO why is BooleanEnum.TRUE.__class__ DynamicDynamicBooleanEnum? It should only have one Dynamic
+        # assert model is BooleanEnum.TRUE
+        assert repr(model) == '<DynamicBooleanEnum: True>'
         with self.assertRaises(petstore_api.ApiValueError):
             BooleanEnum(False)
 
diff --git a/samples/openapi3/client/petstore/python-experimental/tests_manual/test_nullable_string.py b/samples/openapi3/client/petstore/python-experimental/tests_manual/test_nullable_string.py
index 2a704a708464..206e84f4b12b 100644
--- a/samples/openapi3/client/petstore/python-experimental/tests_manual/test_nullable_string.py
+++ b/samples/openapi3/client/petstore/python-experimental/tests_manual/test_nullable_string.py
@@ -10,7 +10,6 @@
 """
 
 
-import sys
 import unittest
 
 import petstore_api
@@ -34,6 +33,7 @@ def testNullableString(self):
         assert isinstance(inst, NullableString)
         assert isinstance(inst, Schema)
         assert inst.is_none() is True
+        assert repr(inst) == '<DynamicNullableString: None>'
 
         inst = NullableString('approved')
         assert isinstance(inst, NullableString)
diff --git a/samples/openapi3/client/petstore/python-experimental/tests_manual/test_string_enum.py b/samples/openapi3/client/petstore/python-experimental/tests_manual/test_string_enum.py
index efba299d9f3c..a877eddfd2ff 100644
--- a/samples/openapi3/client/petstore/python-experimental/tests_manual/test_string_enum.py
+++ b/samples/openapi3/client/petstore/python-experimental/tests_manual/test_string_enum.py
@@ -10,7 +10,6 @@
 """
 
 
-import sys
 import unittest
 
 import petstore_api
@@ -32,12 +31,14 @@ def testStringEnum(self):
         inst = StringEnum(None)
         assert isinstance(inst, StringEnum)
         assert isinstance(inst, NoneClass)
+        assert repr(inst) == '<DynamicStringEnum: None>'
 
         inst = StringEnum('approved')
         assert isinstance(inst, StringEnum)
         assert isinstance(inst, Singleton)
         assert isinstance(inst, str)
         assert inst == 'approved'
+        assert repr(inst) == "<DynamicStringEnum: 'approved'>"
 
         with self.assertRaises(petstore_api.ApiValueError):
             StringEnum('garbage')