BUG: Timestamp == date match stdlib

doc/source/whatsnew/v1.3.0.rst

@@ -155,6 +155,7 @@ Deprecations
 - Deprecating allowing scalars passed to the :class:`Categorical` constructor (:issue:`38433`)
 - Deprecated allowing subclass-specific keyword arguments in the :class:`Index` constructor, use the specific subclass directly instead (:issue:`14093`,:issue:`21311`,:issue:`22315`,:issue:`26974`)
 - Deprecated ``astype`` of datetimelike (``timedelta64[ns]``, ``datetime64[ns]``, ``Datetime64TZDtype``, ``PeriodDtype``) to integer dtypes, use ``values.view(...)`` instead (:issue:`38544`)
+- Deprecated comparison of :class:`Timestamp` object with ``datetime.date`` objects.  Instead of e.g. ``ts <= mydate`` use ``ts <= pd.Timestamp(mydate)`` or ``ts.date() <= mydate`` (:issue:`36131`)
 -
 -
 

pandas/_libs/tslibs/timestamps.pyx

@@ -16,6 +16,7 @@ from numpy cimport int8_t, int64_t, ndarray, uint8_t
 cnp.import_array()
 
 from cpython.datetime cimport (  # alias bc `tzinfo` is a kwarg below
+    PyDate_Check,
     PyDateTime_Check,
     PyDateTime_IMPORT,
     PyDelta_Check,
@@ -281,6 +282,18 @@ cdef class _Timestamp(ABCTimestamp):
                 return np.zeros(other.shape, dtype=np.bool_)
             return NotImplemented
 
+        elif PyDate_Check(other):
+            # returning NotImplemented defers to the `date` implementation
+            #  which incorrectly drops tz and normalizes to midnight
+            #  before comparing
+            # We follow the stdlib datetime behavior of never being equal
+            warnings.warn(
+                "Comparison of Timestamp with datetime.date is deprecated in "
+                "order to match the standard library behavior.  "
+                "In a future version these will be considered non-comparable."
+                "Use ts == pd.Timestamp(dt) instead.", FutureWarning
+            )
+            return NotImplemented
         else:
             return NotImplemented
 

pandas/tests/frame/indexing/test_indexing.py

@@ -1429,7 +1429,10 @@ def test_loc_setitem_datetime_coercion(self):
         assert Timestamp("2008-08-08") == df.loc[0, "c"]
         assert Timestamp("2008-08-08") == df.loc[1, "c"]
         df.loc[2, "c"] = date(2005, 5, 5)
-        assert Timestamp("2005-05-05") == df.loc[2, "c"]
+        with tm.assert_produces_warning(FutureWarning):
+            # Comparing Timestamp to date obj is deprecated
+            assert Timestamp("2005-05-05") == df.loc[2, "c"]
+        assert Timestamp("2005-05-05").date() == df.loc[2, "c"]
 
     def test_loc_setitem_datetimelike_with_inference(self):
         # GH 7592

pandas/tests/scalar/timestamp/test_comparisons.py

@@ -142,6 +142,42 @@ def test_compare_invalid(self):
         assert val != np.float64(1)
         assert val != np.int64(1)
 
+    @pytest.mark.parametrize("tz", [None, "US/Pacific"])
+    def test_compare_date(self, tz):
+        # GH#36131 comparing Timestamp with date object is deprecated
+        ts = Timestamp.now(tz)
+        dt = ts.to_pydatetime().date()
+        # These are incorrectly considered as equal because they
+        #  dispatch to the date comparisons which truncates ts
+
+        for left, right in [(ts, dt), (dt, ts)]:
+            with tm.assert_produces_warning(FutureWarning):
+                assert left == right
+            with tm.assert_produces_warning(FutureWarning):
+                assert not left != right
+            with tm.assert_produces_warning(FutureWarning):
+                assert not left < right
+            with tm.assert_produces_warning(FutureWarning):
+                assert left <= right
+            with tm.assert_produces_warning(FutureWarning):
+                assert not left > right
+            with tm.assert_produces_warning(FutureWarning):
+                assert left >= right
+
+        # Once the deprecation is enforced, the following assertions
+        #  can be enabled:
+        #    assert not left == right
+        #    assert left != right
+        #
+        #    with pytest.raises(TypeError):
+        #        left < right
+        #    with pytest.raises(TypeError):
+        #        left <= right
+        #    with pytest.raises(TypeError):
+        #        left > right
+        #    with pytest.raises(TypeError):
+        #        left >= right
+
     def test_cant_compare_tz_naive_w_aware(self, utc_fixture):
         # see GH#1404
         a = Timestamp("3/12/2012")