diff --git a/Jellyfin.Plugin.MediaCleaner/ScheduledTasks/StaleMediaTask.cs b/Jellyfin.Plugin.MediaCleaner/ScheduledTasks/StaleMediaTask.cs
index 3f8090b..1097631 100644
--- a/Jellyfin.Plugin.MediaCleaner/ScheduledTasks/StaleMediaTask.cs
+++ b/Jellyfin.Plugin.MediaCleaner/ScheduledTasks/StaleMediaTask.cs
@@ -112,7 +112,7 @@ public sealed class StaleMediaTask : IScheduledTask
                     _logger.LogInformation("-------------------------------------------------");
                 }
 
-                var mostRecentUserData = movie.UserData.OrderByDescending(data => data.LastPlayedDate).First();
+                var mostRecentUserData = movie.UserData.OrderByDescending(data => data.LastPlayedDate).Where(data => data.LastPlayedDate != null).First();
 
                 if (Configuration.DebugMode){
                     _logger.LogInformation("Most recent user data: {Movie}", movie);
@@ -217,7 +217,7 @@ public sealed class StaleMediaTask : IScheduledTask
 
                 foreach (var episode in episodesWithUserData)
                 {
-                    var mostRecentUserData = episode.UserData.OrderByDescending(data => data.LastPlayedDate).First();
+                    var mostRecentUserData = episode.UserData.OrderByDescending(data => data.LastPlayedDate).Where(data => data.LastPlayedDate != null).First();
                     if(Configuration.DebugMode){
                         foreach (var property in typeof(UserData).GetProperties())
                         {