You don't shove the eartips into your ear canal. It's meant to rest on the concha and then you slightly press them into the entrance of the ear canal for seal. That's why it hurts.
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Zero Red have wide nozzle, you won't get anything noticeably smaller than small tips they give you, if they don't fit look for different IEMs :/
You’ll get more comfortable tips though, the stock ones are a bit rough compared to something like spinfit w1/cp155/145 or divinus velvet/
like spinfit w1/cp155/145 or divinus velvet
ye I use spinfits, dunus double flange tips, fiios double flange tips, fiio foam tips, dunu foam tips(my favourite most of the time but I can't wear it with wire nozzle stuff, it puts to much pressure to my ear canals) but those won't make it any narrower if he wants something narrower, that was my point, spinfits you can wear shallower and I could see that helping tho
Could go for small divinus velvet tips, I have medium on mine
Fiio Hs18 small are smaller and thinner than most. $5 on AliExpress
I had this problem with my Zero's, Moondrop Spring tips work for me, they are smaller than usual.