Thank you for telling me about the Old man at the club. I checked and it appears to be that if you went trough the Young Man First, that it flags the old man as true as well, which is why he approaches her like a familiar. I have now put in the right flag and it will be corrected next update. I am sorry for the inconvenience.
Also regarding the save. You should not have to use a new save file and be able to use an old one. I am always trying my best to make sure that saves are transferable.