[Bug] Fix various DatetimeIndex comparison bugs

doc/source/whatsnew/v0.24.0.txt

@@ -496,6 +496,9 @@ Datetimelike
 - Fixed bug where two :class:`DateOffset` objects with different ``normalize`` attributes could evaluate as equal (:issue:`21404`)
 - Fixed bug where :meth:`Timestamp.resolution` incorrectly returned 1-microsecond ``timedelta`` instead of 1-nanosecond :class:`Timedelta` (:issue:`21336`,:issue:`21365`)
 - Bug in :func:`to_datetime` that did not consistently return an :class:`Index` when ``box=True`` was specified (:issue:`21864`)
+- Bug in :class:`DatetimeIndex` comparisons where string comparisons incorrectly raises ``TypeError`` (:issue:`22074`)
+- Bug in :class:`DatetimeIndex` comparisons when comparing against ``timedelta64[ns]`` dtyped arrays; in some cases ``TypeError`` was incorrectly raised, in others it incorrectly failed to raise (:issue:`22074`)
+- Bug in :class:`DatetimeIndex` comparisons when comparing against object-dtyped arrays (:issue:`22074`)
 
 Timedelta
 ^^^^^^^^^
@@ -518,6 +521,7 @@ Timezones
 - Bug in :class:`Index` with ``datetime64[ns, tz]`` dtype that did not localize integer data correctly (:issue:`20964`)
 - Bug in :class:`DatetimeIndex` where constructing with an integer and tz would not localize correctly (:issue:`12619`)
 - Fixed bug where :meth:`DataFrame.describe` and :meth:`Series.describe` on tz-aware datetimes did not show `first` and `last` result (:issue:`21328`)
+- Bug in :class:`DatetimeIndex` comparisons failing to raise ``TypeError`` when comparing timezone-aware ``DatetimeIndex`` against ``np.datetime64`` (:issue:`22074`)
 
 Offsets
 ^^^^^^^
@@ -535,6 +539,7 @@ Numeric
 - Bug in :meth:`DataFrame.agg`, :meth:`DataFrame.transform` and :meth:`DataFrame.apply` where,
   when supplied with a list of functions and ``axis=1`` (e.g. ``df.apply(['sum', 'mean'], axis=1)``),
   a ``TypeError`` was wrongly raised. For all three methods such calculation are now done correctly. (:issue:`16679`).
+- Bug in :class:`Series` comparison against datetime-like scalars and arrays (:issue:`22074`)
 -
 
 Strings

pandas/core/arrays/datetimes.py

@@ -5,7 +5,7 @@
 import numpy as np
 from pytz import utc
 
-from pandas._libs import tslib
+from pandas._libs import lib, tslib
 from pandas._libs.tslib import Timestamp, NaT, iNaT
 from pandas._libs.tslibs import (
     normalize_date,
@@ -18,7 +18,7 @@
 
 from pandas.core.dtypes.common import (
     _NS_DTYPE,
-    is_datetimelike,
+    is_object_dtype,
     is_datetime64tz_dtype,
     is_datetime64_dtype,
     is_timedelta64_dtype,
@@ -29,6 +29,7 @@
 
 import pandas.core.common as com
 from pandas.core.algorithms import checked_add_with_arr
+from pandas.core import ops
 
 from pandas.tseries.frequencies import to_offset
 from pandas.tseries.offsets import Tick, Day, generate_range
@@ -99,31 +100,40 @@ def wrapper(self, other):
         meth = getattr(dtl.DatetimeLikeArrayMixin, opname)
 
         if isinstance(other, (datetime, np.datetime64, compat.string_types)):
-            if isinstance(other, datetime):
+            if isinstance(other, (datetime, np.datetime64)):
                 # GH#18435 strings get a pass from tzawareness compat
                 self._assert_tzawareness_compat(other)
 
-            other = _to_m8(other, tz=self.tz)
+            try:
+                other = _to_m8(other, tz=self.tz)
+            except ValueError:
+                # string that cannot be parsed to Timestamp
+                return ops.invalid_comparison(self, other, op)
+
             result = meth(self, other)
             if isna(other):
                 result.fill(nat_result)
+        elif lib.is_scalar(other):
+            return ops.invalid_comparison(self, other, op)
         else:
             if isinstance(other, list):
+                # FIXME: This can break for object-dtype with mixed types
                 other = type(self)(other)
             elif not isinstance(other, (np.ndarray, ABCIndexClass, ABCSeries)):
                 # Following Timestamp convention, __eq__ is all-False
                 # and __ne__ is all True, others raise TypeError.
-                if opname == '__eq__':
-                    return np.zeros(shape=self.shape, dtype=bool)
-                elif opname == '__ne__':
-                    return np.ones(shape=self.shape, dtype=bool)
-                raise TypeError('%s type object %s' %
-                                (type(other), str(other)))
-
-            if is_datetimelike(other):
+                return ops.invalid_comparison(self, other, op)
+
+            if is_object_dtype(other):
+                result = op(self.astype('O'), np.array(other))
+            elif not (is_datetime64_dtype(other) or
+                      is_datetime64tz_dtype(other)):
+                # e.g. is_timedelta64_dtype(other)
+                return ops.invalid_comparison(self, other, op)
+            else:
                 self._assert_tzawareness_compat(other)
+                result = meth(self, np.asarray(other))
 
-            result = meth(self, np.asarray(other))
             result = com.values_from_object(result)
 
             # Make sure to pass an array to result[...]; indexing with
@@ -152,6 +162,10 @@ class DatetimeArrayMixin(dtl.DatetimeLikeArrayMixin):
                  'is_year_end', 'is_leap_year']
     _object_ops = ['weekday_name', 'freq', 'tz']
 
+    # dummy attribute so that datetime.__eq__(DatetimeArray) defers
+    # by returning NotImplemented
+    timetuple = None
+
     # -----------------------------------------------------------------
     # Constructors
 

pandas/core/ops.py

@@ -788,6 +788,35 @@ def mask_cmp_op(x, y, op, allowed_types):
     return result
 
 
+def invalid_comparison(left, right, op):
+    """
+    If a comparison has mismatched types and is not necessarily meaningful,
+    follow python3 conventions by:
+
+        - returning all-False for equality
+        - returning all-True for inequality
+        - raising TypeError otherwise
+
+    Parameters
+    ----------
+    left : array-like
+    right : scalar, array-like
+    op : operator.{eq, ne, lt, le, gt}
+
+    Raises
+    ------
+    TypeError : on inequality comparisons
+    """
+    if op is operator.eq:
+        res_values = np.zeros(left.shape, dtype=bool)
+    elif op is operator.ne:
+        res_values = np.ones(left.shape, dtype=bool)
+    else:
+        raise TypeError("Invalid comparison between dtype={dtype} and {typ}"
+                        .format(dtype=left.dtype, typ=type(right).__name__))
+    return res_values
+
+
 # -----------------------------------------------------------------------------
 # Functions that add arithmetic methods to objects, given arithmetic factory
 # methods
@@ -1259,7 +1288,7 @@ def na_op(x, y):
             result = _comp_method_OBJECT_ARRAY(op, x, y)
 
         elif is_datetimelike_v_numeric(x, y):
-            raise TypeError("invalid type comparison")
+            return invalid_comparison(x, y, op)
 
         else:
 

pandas/tests/frame/test_operators.py

@@ -157,8 +157,20 @@ def test_comparison_invalid(self):
         def check(df, df2):
 
             for (x, y) in [(df, df2), (df2, df)]:
-                pytest.raises(TypeError, lambda: x == y)
-                pytest.raises(TypeError, lambda: x != y)
+                # we expect the result to match Series comparisons for
+                # == and !=, inequalities should raise
+                result = x == y
+                expected = DataFrame({col: x[col] == y[col]
+                                      for col in x.columns},
+                                     index=x.index, columns=x.columns)
+                assert_frame_equal(result, expected)
+
+                result = x != y
+                expected = DataFrame({col: x[col] != y[col]
+                                      for col in x.columns},
+                                     index=x.index, columns=x.columns)
+                assert_frame_equal(result, expected)
+
                 pytest.raises(TypeError, lambda: x >= y)
                 pytest.raises(TypeError, lambda: x > y)
                 pytest.raises(TypeError, lambda: x < y)

pandas/tests/frame/test_query_eval.py

@@ -463,9 +463,13 @@ def test_date_query_with_non_date(self):
         df = DataFrame({'dates': date_range('1/1/2012', periods=n),
                         'nondate': np.arange(n)})
 
-        ops = '==', '!=', '<', '>', '<=', '>='
+        result = df.query('dates == nondate', parser=parser, engine=engine)
+        assert len(result) == 0
 
-        for op in ops:
+        result = df.query('dates != nondate', parser=parser, engine=engine)
+        assert_frame_equal(result, df)
+
+        for op in ['<', '>', '<=', '>=']:
             with pytest.raises(TypeError):
                 df.query('dates %s nondate' % op, parser=parser, engine=engine)
 

pandas/tests/indexes/datetimes/test_arithmetic.py

@@ -275,6 +275,20 @@ def test_comparison_tzawareness_compat(self, op):
         with pytest.raises(TypeError):
             op(ts, dz)
 
+    @pytest.mark.parametrize('op', [operator.eq, operator.ne,
+                                    operator.gt, operator.ge,
+                                    operator.lt, operator.le])
+    @pytest.mark.parametrize('other', [datetime(2016, 1, 1),
+                                       Timestamp('2016-01-01'),
+                                       np.datetime64('2016-01-01')])
+    def test_scalar_comparison_tzawareness(self, op, other, tz_aware_fixture):
+        tz = tz_aware_fixture
+        dti = pd.date_range('2016-01-01', periods=2, tz=tz)
+        with pytest.raises(TypeError):
+            op(dti, other)
+        with pytest.raises(TypeError):
+            op(other, dti)
+
     @pytest.mark.parametrize('op', [operator.eq, operator.ne,
                                     operator.gt, operator.ge,
                                     operator.lt, operator.le])
@@ -290,12 +304,60 @@ def test_nat_comparison_tzawareness(self, op):
         result = op(dti.tz_localize('US/Pacific'), pd.NaT)
         tm.assert_numpy_array_equal(result, expected)
 
-    def test_dti_cmp_int_raises(self):
-        rng = date_range('1/1/2000', periods=10)
+    def test_dti_cmp_str(self, tz_naive_fixture):
+        # GH#22074
+        # regardless of tz, we expect these comparisons are valid
+        tz = tz_naive_fixture
+        rng = date_range('1/1/2000', periods=10, tz=tz)
+        other = '1/1/2000'
+
+        result = rng == other
+        expected = np.array([True] + [False] * 9)
+        tm.assert_numpy_array_equal(result, expected)
+
+        result = rng != other
+        expected = np.array([False] + [True] * 9)
+        tm.assert_numpy_array_equal(result, expected)
+
+        result = rng < other
+        expected = np.array([False] * 10)
+        tm.assert_numpy_array_equal(result, expected)
+
+        result = rng <= other
+        expected = np.array([True] + [False] * 9)
+        tm.assert_numpy_array_equal(result, expected)
+
+        result = rng > other
+        expected = np.array([False] + [True] * 9)
+        tm.assert_numpy_array_equal(result, expected)
+
+        result = rng >= other
+        expected = np.array([True] * 10)
+        tm.assert_numpy_array_equal(result, expected)
+
+    @pytest.mark.parametrize('other', ['foo', 99, 4.0,
+                                       object(), timedelta(days=2)])
+    def test_dti_cmp_scalar_invalid(self, other, tz_naive_fixture):
+        # GH#22074
+        tz = tz_naive_fixture
+        rng = date_range('1/1/2000', periods=10, tz=tz)
+
+        result = rng == other
+        expected = np.array([False] * 10)
+        tm.assert_numpy_array_equal(result, expected)
+
+        result = rng != other
+        expected = np.array([True] * 10)
+        tm.assert_numpy_array_equal(result, expected)
 
-        # raise TypeError for now
         with pytest.raises(TypeError):
-            rng < rng[3].value
+            rng < other
+        with pytest.raises(TypeError):
+            rng <= other
+        with pytest.raises(TypeError):
+            rng > other
+        with pytest.raises(TypeError):
+            rng >= other
 
     def test_dti_cmp_list(self):
         rng = date_range('1/1/2000', periods=10)
@@ -304,6 +366,57 @@ def test_dti_cmp_list(self):
         expected = rng == rng
         tm.assert_numpy_array_equal(result, expected)
 
+    @pytest.mark.parametrize('other', [
+        pd.timedelta_range('1D', periods=10),
+        pd.timedelta_range('1D', periods=10).to_series(),
+        pd.timedelta_range('1D', periods=10).asi8.view('m8[ns]')
+    ], ids=lambda x: type(x).__name__)
+    def test_dti_cmp_tdi_tzawareness(self, other):
+        # GH#22074
+        # reversion test that we _don't_ call _assert_tzawareness_compat
+        # when comparing against TimedeltaIndex
+        dti = date_range('2000-01-01', periods=10, tz='Asia/Tokyo')
+
+        result = dti == other
+        expected = np.array([False] * 10)
+        tm.assert_numpy_array_equal(result, expected)
+
+        result = dti != other
+        expected = np.array([True] * 10)
+        tm.assert_numpy_array_equal(result, expected)
+
+        with pytest.raises(TypeError):
+            dti < other
+        with pytest.raises(TypeError):
+            dti <= other
+        with pytest.raises(TypeError):
+            dti > other
+        with pytest.raises(TypeError):
+            dti >= other
+
+    def test_dti_cmp_object_dtype(self):
+        # GH#22074
+        dti = date_range('2000-01-01', periods=10, tz='Asia/Tokyo')
+
+        other = dti.astype('O')
+
+        result = dti == other
+        expected = np.array([True] * 10)
+        tm.assert_numpy_array_equal(result, expected)
+
+        other = dti.tz_localize(None)
+        with pytest.raises(TypeError):
+            # tzawareness failure
+            dti != other
+
+        other = np.array(list(dti[:5]) + [Timedelta(days=1)] * 5)
+        result = dti == other
+        expected = np.array([True] * 5 + [False] * 5)
+        tm.assert_numpy_array_equal(result, expected)
+
+        with pytest.raises(TypeError):
+            dti >= other
+
 
 class TestDatetimeIndexArithmetic(object):
 

pandas/tests/series/test_operators.py

@@ -238,8 +238,15 @@ def test_comparison_invalid(self):
         s2 = Series(date_range('20010101', periods=5))
 
         for (x, y) in [(s, s2), (s2, s)]:
-            pytest.raises(TypeError, lambda: x == y)
-            pytest.raises(TypeError, lambda: x != y)
+
+            result = x == y
+            expected = Series([False] * 5)
+            assert_series_equal(result, expected)
+
+            result = x != y
+            expected = Series([True] * 5)
+            assert_series_equal(result, expected)
+
             pytest.raises(TypeError, lambda: x >= y)
             pytest.raises(TypeError, lambda: x > y)
             pytest.raises(TypeError, lambda: x < y)