diff --git a/association.go b/association.go
index 09e79ca6..dc731ff8 100644
--- a/association.go
+++ b/association.go
@@ -187,8 +187,11 @@ func (association *Association) Delete(values ...interface{}) error {
 			tx := association.DB.Model(reflect.New(rel.Schema.ModelType).Interface())
 
 			_, pvs := schema.GetIdentityFieldValuesMap(association.DB.Statement.Context, reflectValue, rel.Schema.PrimaryFields)
-			pcolumn, pvalues := schema.ToQueryValues(rel.Schema.Table, rel.Schema.PrimaryFieldDBNames, pvs)
-			conds = append(conds, clause.IN{Column: pcolumn, Values: pvalues})
+			if pcolumn, pvalues := schema.ToQueryValues(rel.Schema.Table, rel.Schema.PrimaryFieldDBNames, pvs); len(pvalues) > 0 {
+				conds = append(conds, clause.IN{Column: pcolumn, Values: pvalues})
+			} else {
+				return ErrPrimaryKeyRequired
+			}
 
 			_, rvs := schema.GetIdentityFieldValuesMapFromValues(association.DB.Statement.Context, values, primaryFields)
 			relColumn, relValues := schema.ToQueryValues(rel.Schema.Table, foreignKeys, rvs)
@@ -199,8 +202,11 @@ func (association *Association) Delete(values ...interface{}) error {
 			tx := association.DB.Model(reflect.New(rel.FieldSchema.ModelType).Interface())
 
 			_, pvs := schema.GetIdentityFieldValuesMap(association.DB.Statement.Context, reflectValue, primaryFields)
-			pcolumn, pvalues := schema.ToQueryValues(rel.FieldSchema.Table, foreignKeys, pvs)
-			conds = append(conds, clause.IN{Column: pcolumn, Values: pvalues})
+			if pcolumn, pvalues := schema.ToQueryValues(rel.FieldSchema.Table, foreignKeys, pvs); len(pvalues) > 0 {
+				conds = append(conds, clause.IN{Column: pcolumn, Values: pvalues})
+			} else {
+				return ErrPrimaryKeyRequired
+			}
 
 			_, rvs := schema.GetIdentityFieldValuesMapFromValues(association.DB.Statement.Context, values, rel.FieldSchema.PrimaryFields)
 			relColumn, relValues := schema.ToQueryValues(rel.FieldSchema.Table, rel.FieldSchema.PrimaryFieldDBNames, rvs)
@@ -229,8 +235,11 @@ func (association *Association) Delete(values ...interface{}) error {
 			}
 
 			_, pvs := schema.GetIdentityFieldValuesMap(association.DB.Statement.Context, reflectValue, primaryFields)
-			pcolumn, pvalues := schema.ToQueryValues(rel.JoinTable.Table, joinPrimaryKeys, pvs)
-			conds = append(conds, clause.IN{Column: pcolumn, Values: pvalues})
+			if pcolumn, pvalues := schema.ToQueryValues(rel.JoinTable.Table, joinPrimaryKeys, pvs); len(pvalues) > 0 {
+				conds = append(conds, clause.IN{Column: pcolumn, Values: pvalues})
+			} else {
+				return ErrPrimaryKeyRequired
+			}
 
 			_, rvs := schema.GetIdentityFieldValuesMapFromValues(association.DB.Statement.Context, values, relPrimaryFields)
 			relColumn, relValues := schema.ToQueryValues(rel.JoinTable.Table, joinRelPrimaryKeys, rvs)
diff --git a/tests/associations_test.go b/tests/associations_test.go
index 32f6525b..bc3dac55 100644
--- a/tests/associations_test.go
+++ b/tests/associations_test.go
@@ -261,3 +261,27 @@ func TestSaveHasManyCircularReference(t *testing.T) {
 			children, parent.Children)
 	}
 }
+
+func TestAssociationError(t *testing.T) {
+	DB = DB.Debug()
+	user := *GetUser("TestAssociationError", Config{Pets: 2, Company: true, Account: true, Languages: 2})
+	DB.Create(&user)
+
+	var user1 User
+	DB.Preload("Company").Preload("Pets").Preload("Account").Preload("Languages").First(&user1)
+
+	var emptyUser User
+	var err error
+	// belongs to
+	err = DB.Model(&emptyUser).Association("Company").Delete(&user1.Company)
+	AssertEqual(t, err, gorm.ErrPrimaryKeyRequired)
+	// has many
+	err = DB.Model(&emptyUser).Association("Pets").Delete(&user1.Pets)
+	AssertEqual(t, err, gorm.ErrPrimaryKeyRequired)
+	// has one
+	err = DB.Model(&emptyUser).Association("Account").Delete(&user1.Account)
+	AssertEqual(t, err, gorm.ErrPrimaryKeyRequired)
+	// many to many
+	err = DB.Model(&emptyUser).Association("Languages").Delete(&user1.Languages)
+	AssertEqual(t, err, gorm.ErrPrimaryKeyRequired)
+}