jsteele wrote:Have you tried different sizes of ear tips? Those can make a big difference.

Totally agree with this. makes a world of difference.
S an option, though, there are over the ear buds like erazer that sit over your ear canal, not in it. Not ideal if you need noise cancelling, but they are comfortable.

Have you tried different sizes of ear tips? Those can make a big difference.

I have tried the old school corded Apple EarPods, AirPods, Bose quiet comfort earbuds and they all hurt my ears! They also seem to fall out (not helpful on an airplane!). I also have the Bose over the ear headphones but they are bulky. Anyone else have this problem and have found a pair that work?