Pressing brake:

Make it slow.

I used to think my entire body should contour along the seat, and I sat too upright, so this was a problem for me as well. Then I realized you’re not actually supposed to rest your head all the time and you can recline the seat to the point where the headrest doesn’t angle forward too much. Just scoot forward a bit if you can’t reach the wheel. Now I drive more relaxed. Also, some cars’ headrests can actually be adjusted forward and back.

Take them all the way out, and flirt it around.

Or see if it moves

Either it is not set right or your head is too long.

Ask Will Toledo.

They shouldn't be uncomfortable. Make sure you've set them correctly.

I always lower the back of the seat as much as possible and raise the front as much as possible so I'm planted in the seat. I can pick up both get without sliding out of the seat. Then I recline a little bit so I can rest my head comfortably. I have seen those more modern headrests that seem to stick way out from the seat. Not sure who those are for.

My mom used to have a car like this. I would remove the head rest every time I had to ride in it.

Just tilt the seat back a bit more?

I am in this picture.

(really need to work on my posture.)