diff --git a/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/encoders/ExpressionEncoder.scala b/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/encoders/ExpressionEncoder.scala
index c97dfe1970c1a..94bd1c9b7da30 100644
--- a/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/encoders/ExpressionEncoder.scala
+++ b/sql/catalyst/src/main/scala/org/apache/spark/sql/catalyst/encoders/ExpressionEncoder.scala
@@ -87,9 +87,13 @@ object ExpressionEncoder {
 
     encoders.foreach(_.assertUnresolved())
 
+    val schema = StructType(encoders.zipWithIndex.map {
+      case (e, i) =>
+        StructField(s"_${i + 1}", e.objSerializer.dataType, e.objSerializer.nullable)
+    })
+
     val cls = Utils.getContextOrSparkClassLoader.loadClass(s"scala.Tuple${encoders.size}")
 
-    val newSerializerInput = BoundReference(0, ObjectType(cls), nullable = true)
     val serializers = encoders.zipWithIndex.map { case (enc, index) =>
       val boundRefs = enc.objSerializer.collect { case b: BoundReference => b }.distinct
       assert(boundRefs.size == 1, "object serializer should have only one bound reference but " +
@@ -97,39 +101,42 @@ object ExpressionEncoder {
 
       val originalInputObject = boundRefs.head
       val newInputObject = Invoke(
-        newSerializerInput,
+        BoundReference(0, ObjectType(cls), nullable = true),
         s"_${index + 1}",
         originalInputObject.dataType,
         returnNullable = originalInputObject.nullable)
 
       val newSerializer = enc.objSerializer.transformUp {
-        case BoundReference(0, _, _) => newInputObject
+        case b: BoundReference => newInputObject
       }
 
       Alias(newSerializer, s"_${index + 1}")()
     }
-    val newSerializer = CreateStruct(serializers)
 
-    val newDeserializerInput = GetColumnByOrdinal(0, newSerializer.dataType)
-    val deserializers = encoders.zipWithIndex.map { case (enc, index) =>
+    val childrenDeserializers = encoders.zipWithIndex.map { case (enc, index) =>
       val getColExprs = enc.objDeserializer.collect { case c: GetColumnByOrdinal => c }.distinct
       assert(getColExprs.size == 1, "object deserializer should have only one " +
         s"`GetColumnByOrdinal`, but there are ${getColExprs.size}")
 
-      val input = GetStructField(newDeserializerInput, index)
-      enc.objDeserializer.transformUp {
+      val input = GetStructField(GetColumnByOrdinal(0, schema), index)
+      val newDeserializer = enc.objDeserializer.transformUp {
         case GetColumnByOrdinal(0, _) => input
       }
+      if (schema(index).nullable) {
+        If(IsNull(input), Literal.create(null, newDeserializer.dataType), newDeserializer)
+      } else {
+        newDeserializer
+      }
     }
-    val newDeserializer = NewInstance(cls, deserializers, ObjectType(cls), propagateNull = false)
 
-    def nullSafe(input: Expression, result: Expression): Expression = {
-      If(IsNull(input), Literal.create(null, result.dataType), result)
-    }
+    val serializer = If(IsNull(BoundReference(0, ObjectType(cls), nullable = true)),
+      Literal.create(null, schema), CreateStruct(serializers))
+    val deserializer =
+      NewInstance(cls, childrenDeserializers, ObjectType(cls), propagateNull = false)
 
     new ExpressionEncoder[Any](
-      nullSafe(newSerializerInput, newSerializer),
-      nullSafe(newDeserializerInput, newDeserializer),
+      serializer,
+      deserializer,
       ClassTag(cls))
   }
 
diff --git a/sql/core/src/test/scala/org/apache/spark/sql/DatasetSuite.scala b/sql/core/src/test/scala/org/apache/spark/sql/DatasetSuite.scala
index 2ce0754a5d1e7..2723122f25c17 100644
--- a/sql/core/src/test/scala/org/apache/spark/sql/DatasetSuite.scala
+++ b/sql/core/src/test/scala/org/apache/spark/sql/DatasetSuite.scala
@@ -29,6 +29,7 @@ import org.apache.spark.TestUtils.withListener
 import org.apache.spark.scheduler.{SparkListener, SparkListenerJobStart}
 import org.apache.spark.sql.catalyst.{FooClassWithEnum, FooEnum, ScroogeLikeExample}
 import org.apache.spark.sql.catalyst.encoders.{OuterScopes, RowEncoder}
+import org.apache.spark.sql.catalyst.expressions.GenericRowWithSchema
 import org.apache.spark.sql.catalyst.plans.{LeftAnti, LeftSemi}
 import org.apache.spark.sql.catalyst.util.sideBySide
 import org.apache.spark.sql.execution.{LogicalRDD, RDDScanExec, SQLExecution}
@@ -2147,6 +2148,50 @@ class DatasetSuite extends QueryTest
       (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12),
       (3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13))
   }
+
+  test("SPARK-37829: DataFrame outer join") {
+    // Same as "SPARK-15441: Dataset outer join" but using DataFrames instead of Datasets
+    val left = Seq(ClassData("a", 1), ClassData("b", 2)).toDF().as("left")
+    val right = Seq(ClassData("x", 2), ClassData("y", 3)).toDF().as("right")
+    val joined = left.joinWith(right, $"left.b" === $"right.b", "left")
+
+    val leftFieldSchema = StructType(
+      Seq(
+        StructField("a", StringType),
+        StructField("b", IntegerType, nullable = false)
+      )
+    )
+    val rightFieldSchema = StructType(
+      Seq(
+        StructField("a", StringType),
+        StructField("b", IntegerType, nullable = false)
+      )
+    )
+    val expectedSchema = StructType(
+      Seq(
+        StructField(
+          "_1",
+          leftFieldSchema,
+          nullable = false
+        ),
+        // This is a left join, so the right output is nullable:
+        StructField(
+          "_2",
+          rightFieldSchema
+        )
+      )
+    )
+    assert(joined.schema === expectedSchema)
+
+    val result = joined.collect().toSet
+    val expected = Set(
+      new GenericRowWithSchema(Array("a", 1), leftFieldSchema) ->
+        null,
+      new GenericRowWithSchema(Array("b", 2), leftFieldSchema) ->
+        new GenericRowWithSchema(Array("x", 2), rightFieldSchema)
+    )
+    assert(result == expected)
+  }
 }
 
 case class Bar(a: Int)