Peter, I’ve been using a blood pressure meter for nearly 30 years, so my response is based on my personal experience and information I’ve acquired over the years. First, I suggest that you take your meter to the doctor and have them check several readings of your meter against theirs. For example, If your meter consistently shows it’s 10 points lower than the doctor’s, just delete the 10 points from your meter reading (have them check both numbers so you can adjust both as necessary). Also, it’s common that many doctor’s offices take your blood pressure incorrectly (you should actually sit still for 5 minutes, with your feet on the floor and the cuff at the same level as your heart) . Some of us have”white coat” hypertension, so you may always be elevated at the doctor’s office. If you are a large man, you (and your doctor’s office) may need to use a larger cuff as the wrong size of cuff can affect your reading. Also, I spoke with customer service at one of the companies that makes many of the home & professional meters, and she told me that the automated machines are not very accurate if you have kidney disease or heart failure (I have both). Ask the doctor’s staff to always use the manual system and it will be more accurate than those noisy automatic ones.
Your doctor may suggest that you check your blood pressure at home. The easiest way to do this is to use a digital blood pressure monitor. You can get a monitor from your local drug store, hospital, clinic or online. Your doctor can help you find a monitor that is right for you and show you how to use it. Many pharmacies and grocery stores also have in-store monitors that you can use for free. 

The cause for hypertension is not always known, although it can develop as a result of other health conditions including: sleep apnea, kidney problems, and thyroid issues. Beyond chronic health conditions, risk factors for hypertension include age, the amount of salt you eat, being overweight or obese, using tobacco, drinking excessively, not exercising, and having too little potassium in your diet.

^ Qaseem, A; Wilt, TJ; Rich, R; Humphrey, LL; Frost, J; Forciea, MA; Clinical Guidelines Committee of the American College of Physicians and the Commission on Health of the Public and Science of the American Academy of Family, Physicians. (21 March 2017). "Pharmacologic Treatment of Hypertension in Adults Aged 60 Years or Older to Higher Versus Lower Blood Pressure Targets: A Clinical Practice Guideline From the American College of Physicians and the American Academy of Family Physicians". Annals of Internal Medicine. 166 (6): 430–437. doi:10.7326/m16-1785. PMID 28135725.

In Europe hypertension occurs in about 30-45% of people as of 2013.[12] In 1995 it was estimated that 43 million people (24% of the population) in the United States had hypertension or were taking antihypertensive medication.[141] By 2004 this had increased to 29%[142][143] and further to 32% (76 million US adults) by 2017.[7] In 2017, with the change in definitions for hypertension, 46% of people in the United States are affected.[7] African-American adults in the United States have among the highest rates of hypertension in the world at 44%.[144] It is also more common in Filipino Americans and less common in US whites and Mexican Americans.[6][145] Differences in hypertension rates are multifactorial and under study.[146]
In the 19th and 20th centuries, before effective pharmacological treatment for hypertension became possible, three treatment modalities were used, all with numerous side-effects: strict sodium restriction (for example the rice diet[152]), sympathectomy (surgical ablation of parts of the sympathetic nervous system), and pyrogen therapy (injection of substances that caused a fever, indirectly reducing blood pressure).[152][158]

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.
If your blood pressure is always on the low side and you do not have any of the above symptoms, there is usually no cause for concern. Similarly, if you have a single at-home blood pressure reading that is abnormally low without any symptoms, you probably do not need to see your doctor. It is normal for your blood pressure to rise and fall over time, and your body is usually able to get your blood pressure back to normal.
In the 19th and 20th centuries, before effective pharmacological treatment for hypertension became possible, three treatment modalities were used, all with numerous side-effects: strict sodium restriction (for example the rice diet[152]), sympathectomy (surgical ablation of parts of the sympathetic nervous system), and pyrogen therapy (injection of substances that caused a fever, indirectly reducing blood pressure).[152][158]
Melissa Conrad Stöppler, MD, is a U.S. board-certified Anatomic Pathologist with subspecialty training in the fields of Experimental and Molecular Pathology. Dr. Stöppler's educational background includes a BA with Highest Distinction from the University of Virginia and an MD from the University of North Carolina. She completed residency training in Anatomic Pathology at Georgetown University followed by subspecialty fellowship training in molecular diagnostics and experimental pathology.
If your blood pressure is always on the low side and you do not have any of the above symptoms, there is usually no cause for concern. Similarly, if you have a single at-home blood pressure reading that is abnormally low without any symptoms, you probably do not need to see your doctor. It is normal for your blood pressure to rise and fall over time, and your body is usually able to get your blood pressure back to normal.
Primary (or essential) hypertension is when the cause is unknown. The majority of hypertension cases are primary. When there is an underlying problem such as kidney disease or hormonal disorders that can cause hypertension, it is called secondary hypertension. When it is possible to correct the underlying cause, high blood pressure usually improves and may even return to normal.
Facial flushing: Facial flushing occurs when blood vessels in the face dilate. It can occur unpredictably or in response to certain triggers such as sun exposure, cold weather, spicy foods, wind, hot drinks and skin-care products. Facial flushing can also occur with emotional stress, exposure to heat or hot water, alcohol consumption and exercise — all of which can raise blood pressure temporarily. While facial flushing may occur while your blood pressure is higher than usual, high blood pressure is not the cause of facial flushing.  
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
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.
It occurs more often in older people who are taking a lot of medication. However, it can cause symptoms in younger people. There may be underlying medical conditions such as joint hypermobility syndrome, diabetes, parkinson’s disease, addison’s disease or autonomic failure. Dehydration, hunger, low body weight and deconditioning (being out of shape/unfit) can reduce blood pressure.
About This Image: Chart showing potential causes of low blood pressure The risk of low and high blood pressure commonly increases as a person ages due in part to changes during the aging process. The flow of blood to a person's heart muscle and brain declines as a person ages, many times as a result of plaque buildup in their blood vessels. Approximately 10-20% of people over the age of 65 experience postural hypotension. While the causes of low blood pressure may not always be clear, it might be associated with things such as:
Normal blood pressure is less than 120/80. Knowing your blood pressure and remembering to check it regularly can help save your life. Choosing healthier, heart-conscious foods, maintaining a healthy weight, getting up and staying active, and managing your stress are great ways to help keep your blood pressure at the level it should be. Learn more about what you can do to help control your blood pressure.
Stress reduction techniques such as biofeedback or transcendental meditation may be considered as an add-on to other treatments to reduce hypertension, but do not have evidence for preventing cardiovascular disease on their own.[125][126][127] Self-monitoring and appointment reminders might support the use of other strategies to improve blood pressure control, but need further evaluation.[128]
The first line of treatment for hypertension is lifestyle changes, including dietary changes, physical exercise, and weight loss. Though these have all been recommended in scientific advisories,[111] a Cochrane systematic review found no evidence for effects of weight loss diets on death, long-term complications or adverse events in persons with hypertension.[112] The review did find a decrease in blood pressure.[112] Their potential effectiveness is similar to and at times exceeds a single medication.[12] If hypertension is high enough to justify immediate use of medications, lifestyle changes are still recommended in conjunction with medication. 

^ Roerecke, Michael; Tobe, Sheldon W.; Kaczorowski, Janusz; Bacon, Simon L.; Vafaei, Afshin; Hasan, Omer S. M.; Krishnan, Rohin J.; Raifu, Amidu O.; Rehm, Jürgen (27 June 2018). "Sex‐Specific Associations Between Alcohol Consumption and Incidence of Hypertension: A Systematic Review and Meta‐Analysis of Cohort Studies". Journal of the American Heart Association. 7 (13): e008202. doi:10.1161/JAHA.117.008202.
Allergic reaction (anaphylaxis): Anaphylactic shock is a sometimes-fatal allergic reaction that can occur in people who are highly sensitive to drugs such as penicillin, to certain foods such as peanuts or to bee or wasp stings. This type of shock is characterized by breathing problems, hives, itching, a swollen throat and a sudden, dramatic fall in blood pressure.
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