I don’t think it’s guaranteed to get that every single time if you do this but pretty much what I do is try to interact with him a few times,pretty much just start going for him right at Monday,make sure at queensgaurd you get his cg then attend a class,I think you have to take the option of hanging out with him in that class and then you’ll get a dialogue about 2 students talking about a dragon and then you should be set!