Bug or..?

In my save, I have a regen centre back from the academy who just turned 24. Last season around Nov-Dec, he said that he had achieved all he wanted at the club and wanted to move on and so we had a chat, I told him "Why leave when you can achive so much more?" or something like that then he said all right, he'll drop it and he's happy to stay at the club. Then 2 months later, he's complaining again and again we have the same chat and the chat goes exactly how it did the last time.

Then right as we're starting the next season, he complains again, we have the same chat and he drops it again. I'm just wondering, is this some sort of really weird bug or do I have to really go through this every bloody 3 months?

He's beginning to get itchy feet. He'll probably keep on wanting to go elsewhere, but putting it off out of respect for your management. Watch his performance levels. If they tail off, he's not fully motivated any more and you should sell him.