This is just a case of working towards it as and when the villagers will tolerate idle chit chat. When you press
to interact with them, press
to chit chat. If they shoo you away, it won’t count. But if they do talk, then it counts towards the total. This was one of the later achievements I unlocked. Just keep trying as you work through their quests as sometimes they won’t have much to say for quite some time.