diff --git a/pandas/core/arrays/datetimelike.py b/pandas/core/arrays/datetimelike.py
index 27b2ed822a49f..63932e64d3b05 100644
--- a/pandas/core/arrays/datetimelike.py
+++ b/pandas/core/arrays/datetimelike.py
@@ -60,29 +60,24 @@ def _datetimelike_array_cmp(cls, op):
     opname = f"__{op.__name__}__"
     nat_result = opname == "__ne__"
 
-    @unpack_zerodim_and_defer(opname)
-    def wrapper(self, other):
+    class InvalidComparison(Exception):
+        pass
 
+    def _validate_comparison_value(self, other):
         if isinstance(other, str):
             try:
                 # GH#18435 strings get a pass from tzawareness compat
                 other = self._scalar_from_string(other)
             except ValueError:
                 # failed to parse as Timestamp/Timedelta/Period
-                return invalid_comparison(self, other, op)
+                raise InvalidComparison(other)
 
         if isinstance(other, self._recognized_scalars) or other is NaT:
             other = self._scalar_type(other)
             self._check_compatible_with(other)
 
-            other_i8 = self._unbox_scalar(other)
-
-            result = op(self.view("i8"), other_i8)
-            if isna(other):
-                result.fill(nat_result)
-
         elif not is_list_like(other):
-            return invalid_comparison(self, other, op)
+            raise InvalidComparison(other)
 
         elif len(other) != len(self):
             raise ValueError("Lengths must match")
@@ -93,34 +88,50 @@ def wrapper(self, other):
                 other = np.array(other)
 
             if not isinstance(other, (np.ndarray, type(self))):
-                return invalid_comparison(self, other, op)
-
-            if is_object_dtype(other):
-                # We have to use comp_method_OBJECT_ARRAY instead of numpy
-                #  comparison otherwise it would fail to raise when
-                #  comparing tz-aware and tz-naive
-                with np.errstate(all="ignore"):
-                    result = ops.comp_method_OBJECT_ARRAY(
-                        op, self.astype(object), other
-                    )
-                o_mask = isna(other)
+                raise InvalidComparison(other)
+
+            elif is_object_dtype(other.dtype):
+                pass
 
             elif not type(self)._is_recognized_dtype(other.dtype):
-                return invalid_comparison(self, other, op)
+                raise InvalidComparison(other)
 
             else:
                 # For PeriodDType this casting is unnecessary
+                # TODO: use Index to do inference?
                 other = type(self)._from_sequence(other)
                 self._check_compatible_with(other)
 
-                result = op(self.view("i8"), other.view("i8"))
-                o_mask = other._isnan
+        return other
 
-            if o_mask.any():
-                result[o_mask] = nat_result
+    @unpack_zerodim_and_defer(opname)
+    def wrapper(self, other):
 
-        if self._hasnans:
-            result[self._isnan] = nat_result
+        try:
+            other = _validate_comparison_value(self, other)
+        except InvalidComparison:
+            return invalid_comparison(self, other, op)
+
+        dtype = getattr(other, "dtype", None)
+        if is_object_dtype(dtype):
+            # We have to use comp_method_OBJECT_ARRAY instead of numpy
+            #  comparison otherwise it would fail to raise when
+            #  comparing tz-aware and tz-naive
+            with np.errstate(all="ignore"):
+                result = ops.comp_method_OBJECT_ARRAY(op, self.astype(object), other)
+            return result
+
+        if isinstance(other, self._scalar_type) or other is NaT:
+            other_i8 = self._unbox_scalar(other)
+        else:
+            # Then type(other) == type(self)
+            other_i8 = other.asi8
+
+        result = op(self.asi8, other_i8)
+
+        o_mask = isna(other)
+        if self._hasnans | np.any(o_mask):
+            result[self._isnan | o_mask] = nat_result
 
         return result