As for when to check your blood pressure, the most important thing is to do it consistently the same time of the day (ask the doctor which time he prefers and also what time in relation to taking your medication). The following article has a lot of good information for someone just starting to monitor their blood pressure: https://www.drugs.com/cg/how-to-take-a-blood-pressure.html
I just started using high blood pressure medication and purchased a blood pressure meter at age 72. what concerns me is that the BP readings I get have a very wide variance in. I measure every morning as soon as I wake up, while still in bed and prior to having any coffee. I take 3 or 4 readings. I have found that on any given day my reading can vary from 126 to 143 systolic and the diastolic reading from 68 to 87. this wide variance makes it very difficult to track trends. My questions are: is this normal? is my instrument possibly defective? How can my cardiac doctor make a decision to put me on life long medication based on SINGLE reading in his office?
If your blood pressure readings are consistently high, you and your doctor will probably discuss treatment strategies. Treatment for high blood pressure often begins with lifestyle changes such as a weight loss and exercise program as well as a low sodium diet. In fact, the AHA recommends adopting these strategies as a means of preventing the development of high blood pressure and heart disease. If these strategies are not successful in lowering your blood pressure, medications may be recommended. 

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When your heart contracts and squeezes blood out into your network of arteries, the pressure inside those blood vessels is at its highest. This is called systolic pressure and it’s the top number on your blood pressure reading. In between beats, the heart relaxes and the pressure drops. This is your diastolic blood pressure, and it’s the reading’s bottom number.
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Typically, more attention is given to systolic blood pressure (the first number) as a major risk factor for cardiovascular disease for people over 50. In most people, systolic blood pressure rises steadily with age due to the increasing stiffness of large arteries, long-term buildup of plaque and an increased incidence of cardiac and vascular disease.
Healthcare professionals use a stethoscope and a manual sphygmomanometer to measure your blood pressure. Typically they take the reading above your elbow. The sphygmomanometer has a bladder, cuff, bulb, and a gauge. When the bulb is pumped it inflates the bladder inside the cuff, which is wrapped around your arm. This inflation will stop the blood flow in your arteries. The stethoscope is used to listen for sound of the heartbeat, and no sound indicates that there is no flow. As the pressure is released from the bladder, you will hear the sound of the blood flowing again. That point becomes systolic reading. The diastolic reading is when you hear no sound again, which means that the blood flow is back to normal.
High blood pressure, also known as hypertension (See blood pressure chart below) is called the “silent killer” for a reason — there are no obvious symptoms but it can result in heart attack, stroke and even death. The good news is there’s a lot you can do to maintain healthy blood pressure or get back to one, often without the need for medications.
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