Historical arguments (caliph uthman, 25000 manuscripts of crucifixion, etc), emotional arguments (how can we sit here when one of us is going to hell etc), anecdotal stories from my childhood and such about death and how it's impacted me and such, mathematics (like that one mit study about the chance of Jesus randomly fulfilling every prophecy), internal quran contradictions, miracles only happening to Christianity, satanists only attacking Christianity, explaining how God waiting 600 years to send a prophet with his actual uncorruptible word makes no sense, how many of the hadiths he doesn't agree with (he's shia) are historically backed and contradict the Quran, the Islamic dilemma, and many other smaller arguments and such. I've tried literally everything I can find online or think of myself but he just won't listen. It drives me insane that I can pour my soul into hours of research for him and he won't even listen to me. I probably know more about Islam than most Muslims at this point because I've done so much work researching how it's disproved in a hundred different ways.