Yes, very much. I don’t even know how many headsets for various things I’ve bought over the years, and every last one hurts my ears or squishes my head or both (and I’m a small person). The least painful I’ve tried is actually sony’s current PS headset, and they are actually heads above all the others… but they do still hurt. My ipod pros fit wonderfully and don’t hurt at all, but trying to get - and keep - a stable PS connection with them is such a pain in the ass that it’s not worth the effort for the amount of time I play in one sitting.