Joe, for whatever it’s worth, I’d like to share an experience on here. It might help other people. However, let me first say that as another poster so aptly stated on this thread, sometimes you have to give up (i.e. wait) certain opportunities until your children are older. People can live without flying.
I was 17 the first time I ever flew on a plane. We flew Cleveland to Los Angeles. I think it was a direct flight. The plane was very big and there was this wonderful recreational area with tables and seats, where I ended up spending time playing cards with my dad and brothers. I no longer recall the craft or airline.
Upon descent, I started experiencing terrible pain in my ears and along my jawline & side of my head. Excruciating. The stewardess brought me gum, but none of the usual “tricks” worked. I thought my head would explode. I sobbed in agony while my poor father did his best to comfort me. Meanwhile, I looked around and saw everyone else smiling and normal; and realized I was the only one experiencing this horror. It took a couple of days for my ears to “pop” and return to normal.
I was terrified to return home and - you guessed it - same deal going back. From then on, I dreaded flying, but I did fly a few more times, always experiencing this same situation; of course, none were ever as bad as the CLE-LA flight.
Sometime in 1988, I met a brilliant doctor through my work. I told him of my experience and he talked to me about how they pressurize the cabins and that some airlines were cheap and didn’t pressurize as well, etc. etc. He told me to take antihistamines before flying. He said I was experiencing what a person who would have a bad cold might experience while flying. Anyway, the end of the story is that I have taken Sudafed before every flight I have ever done since then - I take them about 45 minutes b/f the take-off and throughout the flight. They don’t help if I need to sleep, but it sure beats wanting to rip your hair out. I have had some discomfort on a few trips and literally nothing on more. I can’t imagine what my life would be had my friend not told me of this remedy, since I have traveled all over the world.
The reason I share this story is I have often wondered if some of the small children I have seen do not experience what I have, but they are too little to tell their parents.
I’m not saying this is the case of the toddler having a tantrum,since a 2 year old can talk and show that they are in pain, but I’ve seen babies screaming bloody murder and just cringe wondering if the poor thing has my malady. One never knows.
It sounds like you have some unique physiology that make equalizing your ears difficult. Attempting a valsalva maneuver (pinching your nose closed and trying to exhale against it) with your chin tilted up and head leaned away from the offending ear can sometimes help. It straightens the eustachian tube out a bit.