Hello. Thanks for asking from HCM. I can understand your concern. The headache with heartburn could be due to heartburn itself or cardiac pain causing both. The second headache episode was associated with heartburn or not, it is not clear from your question. But if it was associated with heartburn then give him medicine like pantoprazole domperidone combination after proper prescription. It will neutralise acid and prevent reflux of acid in food pipe. Ask him to stop or decrease intake of fatty, spicy food, late night food intake, chocolates, sweets, tea or coffee. Ask him to sleep with head at higher level then chest. If it relieve his symptoms of both, it means cause was heartburn only. Now coming to our second diagnosis, cardiac disease like angina/minor myocardial infarction. It needs urgent evaluation and treatment from cardiologist. You can suspect it if pain was more on left side of chest going into jaw and left upper limb, occurred after exertion or emotional stress, constricting type chest pain. If second headache was not associated with heartburn, it could be due to multiple causes like tension headache, hypertension, visual blurring or change in number of glasses, migraine. You should consult doctor. He will examine his BP, vision, neurological system to find out the cause. He might advise few investigations to reach unto some diagnosis. Meanwhile you can give him paracetamol or Diclofenac sodium to relieve his headache after proper prescription. Hope it will help you to reach unto some conclusion and you can decide accordingly. Thanks. Take care.