The brain requires unobstructed blood flow to nourish its many functions. Very high, sustained blood pressure will eventually cause blood vessels to weaken. Over time these weaken vessels can break, and blood will leak into the brain. The area of the brain that is being fed by these broken vessels start to die, and this will cause a stroke. Additionally, if a blot clot blocks a narrowed artery, blood ceases to flow and a stroke will occur.
If diet and exercise are not sufficient to lower blood pressure, the first medications recommended are often diuretics or so-called "water pills." These reduce sodium and fluid levels in the body to lower blood pressure. Taking diuretics means you will urinate more frequently. Sometimes, diuretics deplete potassium levels as well, which can lead to muscle weakness, leg cramps, and tiredness. Other side effects of diuretics can include elevated blood sugars in people with diabetes. Less commonly, erectile dysfunction can occur.

A desired blood pressure is less than 120/80. In people who are considered to be healthy, low blood pressure without experiencing any symptoms is commonly not a concern and does not need to be treated. Low blood pressure may be a sign of an underlying issue, particularly in seniors, where it might cause inadequate blood floor to their heart, vital organs, and brain.
Hypertension is rarely accompanied by symptoms, and its identification is usually through screening, or when seeking healthcare for an unrelated problem. Some people with high blood pressure report headaches (particularly at the back of the head and in the morning), as well as lightheadedness, vertigo, tinnitus (buzzing or hissing in the ears), altered vision or fainting episodes.[20] These symptoms, however, might be related to associated anxiety rather than the high blood pressure itself.[21]
Vasovagal syncope can be treated with several types of drugs such as beta blockers, for example, propanolol (Inderal, Inderal LA) and selective serotonin reuptake inhibitors such as fluoxetine (Prozac), escitalopram oxalate (Lexapro), paroxetine (Paxil), sertraline (Zoloft), citalopram (Celexa), and fluvoxamine (Luvox). Fludrocortisone (Florinef) (a drug that prevents dehydration by causing the kidney(s) to retain water) also may be used. A pacemaker can also be helpful when a patient fails drug therapy.

Hypertension with certain specific additional signs and symptoms may suggest secondary hypertension, i.e. hypertension due to an identifiable cause. For example, Cushing's syndrome frequently causes truncal obesity, glucose intolerance, moon face, a hump of fat behind the neck/shoulder (referred to as a buffalo hump), and purple abdominal stretch marks.[23] Hyperthyroidism frequently causes weight loss with increased appetite, fast heart rate, bulging eyes, and tremor. Renal artery stenosis (RAS) may be associated with a localized abdominal bruit to the left or right of the midline (unilateral RAS), or in both locations (bilateral RAS). Coarctation of the aorta frequently causes a decreased blood pressure in the lower extremities relative to the arms, or delayed or absent femoral arterial pulses. Pheochromocytoma may cause abrupt ("paroxysmal") episodes of hypertension accompanied by headache, palpitations, pale appearance, and excessive sweating.[23]

Health care providers measure blood pressure with a sphygmomanometer (sfig-mo-muh-NAH-muh-ter), which has a cuff that's wrapped around the upper arm and pumped up to create pressure. When the cuff is inflated, it squeezes a large artery in the arm, stopping the blood flow for a moment. Blood pressure is measured as air is gradually let out of the cuff, which allows blood to flow through the artery again.
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:

High blood pressure is the most common chronic medical problem prompting visits to primary health care providers in USA. The American Heart Association estimated the direct and indirect costs of high blood pressure in 2010 as $76.6 billion.[144] In the US 80% of people with hypertension are aware of their condition, 71% take some antihypertensive medication, but only 48% of people aware that they have hypertension adequately control it.[144] Adequate management of hypertension can be hampered by inadequacies in the diagnosis, treatment, or control of high blood pressure.[164] Health care providers face many obstacles to achieving blood pressure control, including resistance to taking multiple medications to reach blood pressure goals. People also face the challenges of adhering to medicine schedules and making lifestyle changes. Nonetheless, the achievement of blood pressure goals is possible, and most importantly, lowering blood pressure significantly reduces the risk of death due to heart disease and stroke, the development of other debilitating conditions, and the cost associated with advanced medical care.[165][166]

Blood pressure is the force of your blood pushing against the walls of your arteries. Each time your heart beats, it pumps out blood into the arteries. Your blood pressure is highest when your heart beats, pumping the blood. This is called systolic pressure. When your heart is at rest, between beats, your blood pressure falls. This is the diastolic pressure. Your blood pressure reading uses these two numbers. Usually they're written one above or before the other, such as 120/80. If your blood pressure reading is 90/60 or lower, you have low blood pressure.