Reddit reviews Pro Ear Scuba Diving Mask for all around Ear Protection - All Black Scuba Div...

Diving + earplugs = bad idea. There are some special masks with tubes that connect the ears and the nasal area - check here.

Freedivers can use the normal pinch-nose technique (called Valsalva equalization) for diving up to 30ish meters.

For deeper dives the volume of air in the lungs is too small for the lungs to be able to push it up all the way to the eardrums. Advanced techniques are needed (such as the Frenzel maneuver). You can find more info here for example. Most of them use the tongue or jaw in some way to push the air from the mouth area, through the eustachian tubes up against the eardrums.

These techniques will work up to a certain depth (not sure exactly which, but let's say 120m or so.

However, the current world record for freediving is 214m. How is that possible? Well, a select few world-class freedivers use a technique where they stop during the dive and inject their cavities (eustachian tubes, sinuses etc.) with fluid. Since fluids are incompressible, there's no need to equalize anymore and you can go to whatever depth.

It turns out that depth is around 250m though (that's what Herbert Nitsch reached in an attempt, but had an incident - you can find more online). Also I've heard theories of your larynx getting crushed when you reach a certain depth.

There are special ear covers that you can use! Two of my marine biologist friends have ruptured their eardrums and use these:
https://www.amazon.com/Scuba-Diving-Mask-around-Protection/dp/B0021OZ1PW

I'll be honest, those ear muffs are a real pain in the butt, but they keep your ears totally dry. And bonus, you won't have any problems equalizing!

Try these. I had the same problem, and these helped immensely. They are available on Amazon as well: https://www.amazon.com/Scuba-Diving-Mask-around-Protection/dp/B0021OZ1PW

There are some options.... Vented ear plugs have helped some people (such as Doc's Pro Plugs).

http://www.amazon.com/Scuba-Diving-Mask-around-Protection/dp/B0021OZ1PW
This is also a possible option. I have heard some positive things, but you may need to shave your head to get a proper seal, I don't know.

edit* You should seek out a Doctor who is also a diver to review these options with. Many MDs don't properly understand diving, I work at a dive shop and you should hear the crazy shit people's Doctors have told them.

As far as diving goes, there is a type of mask that covers your ears as well. A few of the instructors I've worked with in the past have used them. Pretty sure your dreams of diving haven't been totally crushed.

Here's an example