diff --git a/python/pyspark/sql/tests.py b/python/pyspark/sql/tests.py
index 80a94a91a87b3..d9656866f833f 100644
--- a/python/pyspark/sql/tests.py
+++ b/python/pyspark/sql/tests.py
@@ -485,6 +485,79 @@ def test_udf_with_array_type(self):
         self.assertEqual(list(range(3)), l1)
         self.assertEqual(1, l2)
 
+    def test_udf_returning_date_time(self):
+        from pyspark.sql.functions import udf
+        from pyspark.sql.types import DateType
+
+        data = self.spark.createDataFrame([(2017, 10, 30)], ['year', 'month', 'day'])
+
+        expected_date = datetime.date(2017, 10, 30)
+        expected_datetime = datetime.datetime(2017, 10, 30)
+
+        # test Python UDF with default returnType=StringType()
+        # Returning a date or datetime object at runtime with such returnType declaration
+        # is a mismatch, which results in a null, as PySpark treats it as unconvertible.
+        py_date_str, py_datetime_str = udf(datetime.date), udf(datetime.datetime)
+        query = data.select(
+            py_date_str(data.year, data.month, data.day).isNull(),
+            py_datetime_str(data.year, data.month, data.day).isNull())
+        [row] = query.collect()
+        self.assertEqual(row[0], True)
+        self.assertEqual(row[1], True)
+
+        query = data.select(
+            py_date_str(data.year, data.month, data.day),
+            py_datetime_str(data.year, data.month, data.day))
+        [row] = query.collect()
+        self.assertEqual(row[0], None)
+        self.assertEqual(row[1], None)
+
+        # test Python UDF with specific returnType matching actual result
+        py_date, py_datetime = udf(datetime.date, DateType()), udf(datetime.datetime, 'timestamp')
+        query = data.select(
+            py_date(data.year, data.month, data.day) == lit(expected_date),
+            py_datetime(data.year, data.month, data.day) == lit(expected_datetime))
+        [row] = query.collect()
+        self.assertEqual(row[0], True)
+        self.assertEqual(row[1], True)
+
+        query = data.select(
+            py_date(data.year, data.month, data.day),
+            py_datetime(data.year, data.month, data.day))
+        [row] = query.collect()
+        self.assertEqual(row[0], expected_date)
+        self.assertEqual(row[1], expected_datetime)
+
+        # test semantic matching of datetime with timezone
+        # class in __main__ is not serializable
+        from pyspark.sql.tests import UTCOffsetTimezone
+        datetime_with_utc0 = datetime.datetime(2017, 10, 30, tzinfo=UTCOffsetTimezone(0))
+        datetime_with_utc1 = datetime.datetime(2017, 10, 30, tzinfo=UTCOffsetTimezone(1))
+        test_udf = udf(lambda: datetime_with_utc0, 'timestamp')
+        query = data.select(
+            test_udf() == lit(datetime_with_utc0),
+            test_udf() > lit(datetime_with_utc1),
+            test_udf()
+        )
+        [row] = query.collect()
+        self.assertEqual(row[0], True)
+        self.assertEqual(row[1], True)
+        # Note: datetime returned from PySpark is always naive (timezone unaware).
+        #       It currently respects Python's current local timezone.
+        self.assertEqual(row[2].tzinfo, None)
+
+        # tzinfo=None is really the same as not specifying it: a naive datetime object
+        # Just adding a test case for it here for completeness
+        datetime_with_null_timezone = datetime.datetime(2017, 10, 30, tzinfo=None)
+        test_udf = udf(lambda: datetime_with_null_timezone, 'timestamp')
+        query = data.select(
+            test_udf() == lit(datetime_with_null_timezone),
+            test_udf()
+        )
+        [row] = query.collect()
+        self.assertEqual(row[0], True)
+        self.assertEqual(row[1], datetime_with_null_timezone)
+
     def test_broadcast_in_udf(self):
         bar = {"a": "aa", "b": "bb", "c": "abc"}
         foo = self.sc.broadcast(bar)
diff --git a/sql/core/src/main/scala/org/apache/spark/sql/execution/python/EvaluatePython.scala b/sql/core/src/main/scala/org/apache/spark/sql/execution/python/EvaluatePython.scala
index 520afad287648..ec9fc2612bf95 100644
--- a/sql/core/src/main/scala/org/apache/spark/sql/execution/python/EvaluatePython.scala
+++ b/sql/core/src/main/scala/org/apache/spark/sql/execution/python/EvaluatePython.scala
@@ -19,6 +19,7 @@ package org.apache.spark.sql.execution.python
 
 import java.io.OutputStream
 import java.nio.charset.StandardCharsets
+import java.util.Calendar
 
 import scala.collection.JavaConverters._
 
@@ -144,6 +145,7 @@ object EvaluatePython {
     }
 
     case StringType => (obj: Any) => nullSafeConvert(obj) {
+      case _: Calendar => null
       case _ => UTF8String.fromString(obj.toString)
     }