Hello Sean,
It seems you have sensitive ears. Did you have a
cold before flying? It is suggested not to fly if you have sensitive ears and cold. The ears often get clogged. This type of clogging is also indicative of a
sinus problem with which you are not aware of. You should consult a doctor, get X-ray PNS done to rule out any sinus problem. If you are diagnosed with one, you should start on with the treatments immediately to get rid of your clogged ears. You may need a nasal or sinus spray.
Swallowing, yawning and chewing hard food or chewing gums can help your ears get relieved of the pressure. The following mechanism can be of help to you. Try doing it. Inhale air and hold it, pinch your nose between your fingers and gently blow out the air off your plugged nose, repeat it. If you are able to hear a pop sound you are successful in letting out the pressure from within your clogged ear.
Since you have sensitive ears you should take a decongestant tablet a day before flying, this will help to clear out congestion. You can also take a decongestant tab an hour before flying. Do not sleep before landing. You should take sips of water or chew a gum to keep swallowing so that you are able to adjust with the cabin pressure. To let passengers get
oxygen at high altitudes the cabins of airplanes are pressurized and the cabins pressures are adjusted prior to descent. People with sensitive ears experience slight discomfort.
If you have much problems just inform the crew, they are very co-operative. Do not fiddle with your ears. You will get relieved of the clogging soon.