Your total blood pressure reading is determined by measuring your systolic and diastolic blood pressures. Systolic blood pressure, the top number, measures the force your heart exerts on the walls of your arteries each time it beats. Diastolic blood pressure, the bottom number, measures the force your heart exerts on the walls of your arteries in between beats.
About This Image: Person receiving a blood pressure test. Medical research shows that as we age blood pressure rises slightly to accommodate an increased demand of oxygen and nutrients. It is completely natural for the first number (systolic) to be 100 plus our age. A recent study by a group of UCLA researchers came very close to corroborating Dr. Piette's guide for blood pressure of 100 plus your age for men, subtracting 10 for women, and this is after this rule had been in use for five or more decades. Are we now being taught that Dr. Piette's guide for blood pressure is wrong merely for drug company profit?
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

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.
Blood pressure refers to the force exerted by circulating blood on the walls of blood vessels and constitutes one of the principal vital signs. The pressure of the circulating blood decreases as blood moves through arteries, arterioles, capillaries, and veins; the term blood pressure generally refers to arterial pressure, i.e., the pressure in the larger arteries, arteries being the blood vessels which take blood away from the heart.
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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