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
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.
If you had previously been diagnosed with high blood pressure, the new guidelines don't affect you too much, says Dr. Conlin, as you still need to continue your efforts to lower it through medication, diet, exercise, and weight loss. "However, based on new information in the guidelines, your doctor may propose treating your blood pressure to a lower level," he says.
The new guidelines stem from the 2017 results of the Systolic Blood Pressure Intervention Trial (SPRINT), which studied more than 9,000 adults ages 50 and older who had systolic blood pressure (the top number in a reading) of 130 mm Hg or higher and at least one risk factor for cardiovascular disease. The study's aim was to find out whether treating blood pressure to lower the systolic number to 120 mm Hg or less was superior to the standard target of 140 mm Hg or less. The results found that targeting a systolic pressure of no more than 120 mm Hg reduced the chance of heart attacks, heart failure, or stroke over a three-year period.

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.
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