If he has cluster headaches they are very signature, I'd tell him to research into it, however if he's not into research ask him where it hurts.
Cluster Headaches are caused by vaso-dilation on the TMJ Vessel (Right above the joint where your jaw meets your skull) and another vessel behind the eye (same side). What this feels like is a spike going through your TMJ and poking the back of the eye wedging it out of the socket. I also generally have muscle pain in my neck and back (specifically the rhomboid)
If he has these symptoms first, he should see a doctor to get an abortant pill such as Sumatriptan or Eletriptan (which is what I've been taking) Psychedelics work by preventing the headache, in my experience it hasn't ever aborted one of my headaches.
If you have any more questions about cluster headaches let me know!
Also, How old is he?
Creator help me live in a way that will make my ancestors proud.