diff --git a/stdlib/3/pathlib.pyi b/stdlib/3/pathlib.pyi
index 42968fa98..fb06c65e0 100644
--- a/stdlib/3/pathlib.pyi
+++ b/stdlib/3/pathlib.pyi
@@ -30,7 +30,10 @@ class PurePath(_PurePathBase):
     def __le__(self, other: PurePath) -> bool: ...
     def __gt__(self, other: PurePath) -> bool: ...
     def __ge__(self, other: PurePath) -> bool: ...
-    def __truediv__(self: _P, key: Union[str, PurePath]) -> _P: ...
+    if sys.version_info < (3, 6):
+        def __truediv__(self: _P, key: Union[str, PurePath]) -> _P: ...
+    else:
+        def __truediv__(self: _P, key: Union[str, os.PathLike[str]]) -> _P: ...
     if sys.version_info < (3,):
         def __div__(self: _P, key: Union[str, PurePath]) -> _P: ...
     def __bytes__(self) -> bytes: ...
@@ -39,10 +42,16 @@ class PurePath(_PurePathBase):
     def is_absolute(self) -> bool: ...
     def is_reserved(self) -> bool: ...
     def match(self, path_pattern: str) -> bool: ...
-    def relative_to(self: _P, *other: Union[str, PurePath]) -> _P: ...
+    if sys.version_info < (3, 6):
+        def relative_to(self: _P, *other: Union[str, PurePath]) -> _P: ...
+    else:
+        def relative_to(self: _P, *other: Union[str, os.PathLike[str]]) -> _P: ...
     def with_name(self: _P, name: str) -> _P: ...
     def with_suffix(self: _P, suffix: str) -> _P: ...
-    def joinpath(self: _P, *other: Union[str, PurePath]) -> _P: ...
+    if sys.version_info < (3, 6):
+        def joinpath(self: _P, *other: Union[str, PurePath]) -> _P: ...
+    else:
+        def joinpath(self: _P, *other: Union[str, os.PathLike[str]]) -> _P: ...
 
     @property
     def parents(self: _P) -> Sequence[_P]: ...
diff --git a/third_party/2/pathlib2.pyi b/third_party/2/pathlib2.pyi
index 42968fa98..fb06c65e0 100644
--- a/third_party/2/pathlib2.pyi
+++ b/third_party/2/pathlib2.pyi
@@ -30,7 +30,10 @@ class PurePath(_PurePathBase):
     def __le__(self, other: PurePath) -> bool: ...
     def __gt__(self, other: PurePath) -> bool: ...
     def __ge__(self, other: PurePath) -> bool: ...
-    def __truediv__(self: _P, key: Union[str, PurePath]) -> _P: ...
+    if sys.version_info < (3, 6):
+        def __truediv__(self: _P, key: Union[str, PurePath]) -> _P: ...
+    else:
+        def __truediv__(self: _P, key: Union[str, os.PathLike[str]]) -> _P: ...
     if sys.version_info < (3,):
         def __div__(self: _P, key: Union[str, PurePath]) -> _P: ...
     def __bytes__(self) -> bytes: ...
@@ -39,10 +42,16 @@ class PurePath(_PurePathBase):
     def is_absolute(self) -> bool: ...
     def is_reserved(self) -> bool: ...
     def match(self, path_pattern: str) -> bool: ...
-    def relative_to(self: _P, *other: Union[str, PurePath]) -> _P: ...
+    if sys.version_info < (3, 6):
+        def relative_to(self: _P, *other: Union[str, PurePath]) -> _P: ...
+    else:
+        def relative_to(self: _P, *other: Union[str, os.PathLike[str]]) -> _P: ...
     def with_name(self: _P, name: str) -> _P: ...
     def with_suffix(self: _P, suffix: str) -> _P: ...
-    def joinpath(self: _P, *other: Union[str, PurePath]) -> _P: ...
+    if sys.version_info < (3, 6):
+        def joinpath(self: _P, *other: Union[str, PurePath]) -> _P: ...
+    else:
+        def joinpath(self: _P, *other: Union[str, os.PathLike[str]]) -> _P: ...
 
     @property
     def parents(self: _P) -> Sequence[_P]: ...