Have you actually tried the AirPods Pro?

I've always used in-ear headphones but also always felt fatigue from the pressure.

But the AirPods just don't have it. It's more like they sit at the edge of your ear instead of burrowing inside it, and they explicitly use some kind of vent to equalize pressure as well.

Visually, these look like they operate in roughly the same way.

I've tried them, it's definitely an issue still. If I place them at the edge of my ear they just fall out. Tried the different sizes too. I never used in-ear prior in my life, so I assume I'm just not used to it.

I've tried everything including the Airpods Pro, and the only earbuds small enough to not cause my ears discomfort are the Klipsch X11i and X12i. They use some of the smallest balanced armature drivers made by Bosch.

Have you tried comply-style foam tips? I feel pressure with the standard silicone tips that iems tend to come with, but I've been able to wear foam ones for hours without discomfort. The only issue imo is that the foam tips do wear out and break down over time. I haven't actually tracked how long they last, but from memory I think I get about 6 months out of a pair of foam earbud tips.

I don’t like them either. I also don’t like the sound isolation. It makes me feel sort of numb and out of touch when I walk around with such headphones.

I really dislike trying to have conversations on a mic that uses a closed design. I can't really hear myself so I feel like I end up talking very loud.

No earbuds fit me, though I don't see anything immediately wrong with my ears.

I use IEM because the regular old plastic ones that sit in the ear give me actual physical pain after 5 minutes of them just sitting there, it's incredible. And the only brand of IEM that don't fall off are BOSE ones, which are oval shaped and have that little stability wing like these ones from Google.

I don't really have that problem but I noticed that tips that fit help a lot. They are usually interchangeable and come in several sizes.

In my case, the most comfortable tips came from a no-name cheap pair. So I guess it is one area where fit is more important than anything else.

It would be amazing if some sort of wireless headphones like these Google Buds or Apple Airpods could be done over the ear, like:

http://tinyurl.com/yb6qfpes (Koss over-the-ear headphones example)

I was about to come in and ask if anyone knows if the pixel buds or air pods take into consideration differences in ear canal sizes.

The airpods pro have changeable rubber tips and come with 3 sizes for different ear canals.

Every alternative I've used has also had the 3 sizes.