Hey Chronic, I would err on the side of definitely bringing this up with him. It is too much uncertainty for you if you're not sure if he's doing it on purpose. It is painful enough when we open up to someone and they tread on a sensitive area. To be so stoic if you're not sure it's on purpose... that's a really difficult conversation to have but I am pretty sure just bringing it up will help you get to an answer.
Sorry it's painful!