Short answer. From very recent and personal experience, Yes. Of course I was wondering the same thing, and a doctor and other healthcare provider told me 3 days before my flight that "it would really hurt." Another friend warned that my ear drums might pop. At the time I went to the doctor both ears were blocked and I was having ear pain, so I was prescribed antibiotics. The next morning, one of my ears was leaking fluid, so I was really glad I had the antibiotics, which promptly cleared up both the ear pain and the secretions, but, alas, not the blocked Eustachian tubes. Three days later, I got on an airplane expecting the worst. I did take Sudafed decongestant before getting on, which helped my nasal passages but didn't touch the ear blockage. Well, "all" that happened as the plane ascended was a fireworks display going off in my ears! Lots of popping and cracking, but fortunately no pain. And it was that way for 3 more flights. Now, 2 weeks later I still have the blocked ears, but the pain has not returned.
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