Last year, new guidelines from the American Heart Association, the American College of Cardiology, and nine other health organizations lowered the numbers for the diagnosis of hypertension (high blood pressure) to 130/80 millimeters of mercury (mm Hg) and higher for all adults. The previous guidelines set the threshold at 140/90 mm Hg for people younger than age 65 and 150/80 mm Hg for those ages 65 and older.
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.
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.