+1 for seeing your ENT (Ears Nose Throat doctor)
Preferably one with some scuba knowledge and/or background.
I'll jump the gun and also say that you probably don't know how to equalize properly and safely when you're diving down to the bottom of the pool.
Your scuba instructor usually gives you a very brief, and I really mean BRIEF, intro into how to clear you ears. Usually it's a simple method, the Valsalva Maneuver. They tell you how to do it and from there on out it's all on you to perfect your technique.
You can also look into other methods such as:
- yawning
- wiggling your jaw side to side
- Frenzel Method (perfect for freediving without scuba)
- Voluntary Tubal Opening (VTO) or Beance Tubaire Volontaire (BTO)
as well as a few others.
If you do these methods on land you should hear a small to big "pop" in your ears.
I'll set some links to give you an intro:
Freediving Explained - How to Freedive Manual: Equalization Techniques
How to Equalize Your Ears for Scuba Diving - Ear Equalization Basics and Tips for Dealing With Equalization Problems
As for getting water in your ears, they make special ear plugs for divers called Doc Pro Plugs.
Regular ear plugs will plug your ears and prevent you from equalizing properly, you can seriously damage your ears. In fact, regular ear plugs will probably hurt more when you dive down, than if you didn't wear them at all.
Doc Pro Plugs however are different, they have a small vent in them that allows you more time to equalize as you're diving. I've never used them, but I have heard great things from my friends who do.
Doc's Proplugs: The Doctor's Choice for Ear Protection
So as you can see there are ways around this, but first see your ENT. There could be other problems we don't know about. Your ENT will tell you if your tubes will allow you to dive or not.