I've always had some issues with my right ear and also with a congested nose.
Recently, flying to a vacation with a stopover, I had really bad pain on both flights, including major sensations of movement within my ear (not a "pop", there was no relief). This started within about 20-30 minutes of takeoff, lasted about 15 minutes then slowly subsided. The next day my ear started bleeding and I went to see an ear specialist doctor who confirmed a heavily ruptured eardrum. This was a guy who worked, among other things, with navy submariners.
The doctor's recommendation was to always use nasal spray when you fly, if you have this kind of problems. Use it before takeoff and again before landing. You can supplement that with chewing gum, but your first line of defense is clearing your nasal cavities with a spray - those were his exact recommendations.
His recommendation was Afrin, but I don't think it has much to do with the brand, but rather the active ingredient, oxymetazoline. For those concerned that this is an endorsement: I never use nasal spray - there is, among other things, the risk of becoming dependent on it given long term usage.
Flying back was fairly uneventful though my ear did register some pressure on the first flight out.
I researched "ruptured eardrums" to figure out my risks of long term hearing loss and flying is listed a major cause of ruptured eardrums. Luckily, most hearing loss is temporary and goes away within a few weeks or months, mine's pretty much back to normal after 3 weeks.
(I also took this as a vindication of always traveling with health insurance, preferably zero-deductible. If something goes wrong, you want to be able to check it out right away and not second-guess whether you're OK or not - this could easily have led to a major infection, esp being in the tropics).
And, BTW, pinching nose and blowing? certainly didn't work in this case, though I know it and it usually does for me. On the plus side, doctor didn't seem to think it made things worse either. And he did say too, that once blown, the eardrum leak equalizes pressure, so it's a one-off mess - i.e. you need to fix it, but you don't need to panic at flying right there and then.