diff --git a/addons/escoria-core/game/core-scripts/esc/types/esc_dialog.gd b/addons/escoria-core/game/core-scripts/esc/types/esc_dialog.gd
index 0b89d3d9..77fe9d5c 100644
--- a/addons/escoria-core/game/core-scripts/esc/types/esc_dialog.gd
+++ b/addons/escoria-core/game/core-scripts/esc/types/esc_dialog.gd
@@ -90,9 +90,17 @@ func run():
 		escoria.dialog_player,
 		"option_chosen"
 	) as ESCDialogOption
-	var rc = option.run()
-	if rc is GDScriptFunctionState:
-		rc = yield(rc, "completed")
-	if rc != ESCExecution.RC_CANCEL:
-		return self.run()
+
+	var rc = ESCExecution.RC_OK
+
+	# If no valid option was returned, it means this level of dialog is done.
+	# If this is the case and the current level of dialog has a parent, it means
+	# it is still yielding and so will be shown again.
+	if option:
+		rc = option.run()
+		if rc is GDScriptFunctionState:
+			rc = yield(rc, "completed")
+		if rc != ESCExecution.RC_CANCEL:
+			return self.run()
+
 	return rc
diff --git a/addons/escoria-dialog-simple/chooser/simple.gd b/addons/escoria-dialog-simple/chooser/simple.gd
index 5b5b1fa7..278629af 100644
--- a/addons/escoria-dialog-simple/chooser/simple.gd
+++ b/addons/escoria-dialog-simple/chooser/simple.gd
@@ -2,10 +2,14 @@
 # Supports timeout and avatar display
 extends ESCDialogOptionsChooser
 
+
 export(Color, RGB) var color_normal = Color(1.0,1.0,1.0,1.0)
 export(Color, RGB) var color_hover = Color(165.0,42.0,42.0, 1.0)
 
 
+var _no_more_options: bool = false
+
+
 # Hide the chooser at the start just to be safe
 func _ready() -> void:
 	hide_chooser()
@@ -40,6 +44,15 @@ func show_chooser():
 				option
 			])
 
+	# If we've no options left, signify as much and start the timer with a
+	# very short interval so the appropriate signal can be fired. Note that
+	# we have to fire the signal AFTER this method returns as the caller
+	# is almost certainly yielding after this method returns.
+	if _vbox.get_child_count() == 0:
+		_no_more_options = true
+		$Timer.start(0.05)
+		return
+
 	if self.dialog.avatar != "-":
 		$AvatarContainer.add_child(
 			ResourceLoader.load(self.dialog.avatar).instance()
@@ -76,7 +89,9 @@ func _on_answer_selected(option: ESCDialogOption):
 
 # The timeout came and a option was selected
 func _on_Timer_timeout() -> void:
-	_option_chosen(self.dialog.options[self.dialog.timeout_option - 1])
+	var option_chosen = null if _no_more_options else self.dialog.options[self.dialog.timeout_option - 1]
+	_no_more_options = false
+	_option_chosen(option_chosen)
 
 
 # Remove the avatar