diff --git a/pandas/core/arrays/datetimelike.py b/pandas/core/arrays/datetimelike.py
index cc2c753857032..de0a246861961 100644
--- a/pandas/core/arrays/datetimelike.py
+++ b/pandas/core/arrays/datetimelike.py
@@ -444,7 +444,7 @@ def _validate_comparison_value(self, other, opname: str):
 
         else:
             try:
-                other = self._validate_listlike(other, opname, allow_object=True)
+                other = self._validate_listlike(other, allow_object=True)
                 self._check_compatible_with(other)
             except TypeError as err:
                 if is_object_dtype(getattr(other, "dtype", None)):
@@ -548,7 +548,7 @@ def _validate_scalar(self, value, msg: Optional[str] = None):
 
         return value
 
-    def _validate_listlike(self, value, opname: str, allow_object: bool = False):
+    def _validate_listlike(self, value, allow_object: bool = False):
         if isinstance(value, type(self)):
             return value
 
@@ -578,10 +578,9 @@ def _validate_listlike(self, value, opname: str, allow_object: bool = False):
 
         elif not type(self)._is_recognized_dtype(value.dtype):
             raise TypeError(
-                f"{opname} requires compatible dtype or scalar, "
-                f"not {type(value).__name__}"
+                f"value should be a '{self._scalar_type.__name__}', 'NaT', "
+                f"or array of those. Got '{type(value).__name__}' instead."
             )
-
         return value
 
     def _validate_searchsorted_value(self, value):
@@ -589,7 +588,7 @@ def _validate_searchsorted_value(self, value):
         if not is_list_like(value):
             value = self._validate_scalar(value, msg)
         else:
-            value = self._validate_listlike(value, "searchsorted")
+            value = self._validate_listlike(value)
 
         rv = self._unbox(value)
         return self._rebox_native(rv)
@@ -600,7 +599,7 @@ def _validate_setitem_value(self, value):
             f"or array of those. Got '{type(value).__name__}' instead."
         )
         if is_list_like(value):
-            value = self._validate_listlike(value, "setitem")
+            value = self._validate_listlike(value)
         else:
             value = self._validate_scalar(value, msg)
 
@@ -622,7 +621,7 @@ def _validate_where_value(self, other):
         if not is_list_like(other):
             other = self._validate_scalar(other, msg)
         else:
-            other = self._validate_listlike(other, "where")
+            other = self._validate_listlike(other)
 
         return self._unbox(other, setitem=True)
 
diff --git a/pandas/core/indexes/datetimelike.py b/pandas/core/indexes/datetimelike.py
index d6d8cb267e06b..b6836a0bbe496 100644
--- a/pandas/core/indexes/datetimelike.py
+++ b/pandas/core/indexes/datetimelike.py
@@ -663,9 +663,7 @@ def _wrap_joined_index(self, joined: np.ndarray, other):
     @doc(Index._convert_arr_indexer)
     def _convert_arr_indexer(self, keyarr):
         try:
-            return self._data._validate_listlike(
-                keyarr, "convert_arr_indexer", allow_object=True
-            )
+            return self._data._validate_listlike(keyarr, allow_object=True)
         except (ValueError, TypeError):
             return com.asarray_tuplesafe(keyarr)
 
diff --git a/pandas/tests/arrays/test_datetimelike.py b/pandas/tests/arrays/test_datetimelike.py
index a961cf14b2e5c..ed7c7c31c6b8d 100644
--- a/pandas/tests/arrays/test_datetimelike.py
+++ b/pandas/tests/arrays/test_datetimelike.py
@@ -416,7 +416,10 @@ def test_setitem_raises(self):
     def test_setitem_numeric_raises(self, arr1d, box):
         # We dont case e.g. int64 to our own dtype for setitem
 
-        msg = "requires compatible dtype"
+        msg = (
+            f"value should be a '{arr1d._scalar_type.__name__}', "
+            "'NaT', or array of those. Got"
+        )
         with pytest.raises(TypeError, match=msg):
             arr1d[:2] = box([0, 1])
 
diff --git a/pandas/tests/arrays/test_datetimes.py b/pandas/tests/arrays/test_datetimes.py
index 9f136b4979bb7..78721fc2fe1c1 100644
--- a/pandas/tests/arrays/test_datetimes.py
+++ b/pandas/tests/arrays/test_datetimes.py
@@ -396,7 +396,7 @@ def test_searchsorted_invalid_types(self, other, index):
         msg = "|".join(
             [
                 "searchsorted requires compatible dtype or scalar",
-                "Unexpected type for 'value'",
+                "value should be a 'Timestamp', 'NaT', or array of those. Got",
             ]
         )
         with pytest.raises(TypeError, match=msg):
diff --git a/pandas/tests/arrays/test_timedeltas.py b/pandas/tests/arrays/test_timedeltas.py
index b3b8f4d55e4de..75d6f7d276518 100644
--- a/pandas/tests/arrays/test_timedeltas.py
+++ b/pandas/tests/arrays/test_timedeltas.py
@@ -136,7 +136,7 @@ def test_searchsorted_invalid_types(self, other, index):
         msg = "|".join(
             [
                 "searchsorted requires compatible dtype or scalar",
-                "Unexpected type for 'value'",
+                "value should be a 'Timedelta', 'NaT', or array of those. Got",
             ]
         )
         with pytest.raises(TypeError, match=msg):
diff --git a/pandas/tests/indexes/period/test_searchsorted.py b/pandas/tests/indexes/period/test_searchsorted.py
index f2950b9f6065c..6ffdbbfcd2ce6 100644
--- a/pandas/tests/indexes/period/test_searchsorted.py
+++ b/pandas/tests/indexes/period/test_searchsorted.py
@@ -62,7 +62,7 @@ def test_searchsorted_invalid(self):
         msg = "|".join(
             [
                 "searchsorted requires compatible dtype or scalar",
-                "Unexpected type for 'value'",
+                "value should be a 'Period', 'NaT', or array of those. Got",
             ]
         )
         with pytest.raises(TypeError, match=msg):
diff --git a/pandas/tests/indexes/timedeltas/test_searchsorted.py b/pandas/tests/indexes/timedeltas/test_searchsorted.py
index 3cf45931cf6b7..e3b52058469f0 100644
--- a/pandas/tests/indexes/timedeltas/test_searchsorted.py
+++ b/pandas/tests/indexes/timedeltas/test_searchsorted.py
@@ -21,6 +21,6 @@ def test_searchsorted_different_argument_classes(self, klass):
     )
     def test_searchsorted_invalid_argument_dtype(self, arg):
         idx = TimedeltaIndex(["1 day", "2 days", "3 days"])
-        msg = "searchsorted requires compatible dtype"
+        msg = "value should be a 'Timedelta', 'NaT', or array of those. Got"
         with pytest.raises(TypeError, match=msg):
             idx.searchsorted(arg)