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 the systolic pressure drops below 90 mm Hg and the diastolic pressure falls below 60 mm Hg, this is categorized as low blood pressure. Some people may have low pressure all the time and this may be normal for them. If they do not experience any other signs or symptoms, medical treatment may not be necessary for them. Low blood pressure becomes a concern when it is accompanied by noticeable symptoms, such as dizziness, fainting and, in severe cases, shock. When this occurs, people should seek medical attention to determine if an underlying condition may be responsible for their hypotension.
During relaxation of the heart (diastole), the left ventricle of the heart fills with blood returning from the lungs. The left ventricle then contracts and pumps blood into the arteries (systole). The blood pressure in the arteries during contraction of the ventricle (systolic pressure) is higher because blood is being actively ejected into the arteries. It is lower during relaxation of the ventricle (diastolic pressure) when no blood is being ejected into the arteries. The pulse we feel when we place our fingers over an artery is caused by the contraction of the left ventricle and the ejection of blood.
Blood pressure is measured with a blood pressure cuff (sphygmomanometer). This may be done using a stethoscope and a cuff and gauge or by an automatic machine. It is a routine part of the physical examination and one of the vital signs often recorded for a patient visit. Other vital signs include pulse rate, respiratory rate (breathing rate), temperature, and weight.
^ Mente, Andrew; O'Donnell, Martin; Rangarajan, Sumathy; Dagenais, Gilles; Lear, Scott; McQueen, Matthew; Diaz, Rafael; Avezum, Alvaro; Lopez-Jaramillo, Patricio; Lanas, Fernando; Li, Wei; Lu, Yin; Yi, Sun; Rensheng, Lei; Iqbal, Romaina; Mony, Prem; Yusuf, Rita; Yusoff, Khalid; Szuba, Andrzej; Oguz, Aytekin; Rosengren, Annika; Bahonar, Ahmad; Yusufali, Afzalhussein; Schutte, Aletta Elisabeth; Chifamba, Jephat; Mann, Johannes F E; Anand, Sonia S; Teo, Koon; Yusuf, S (July 2016). "Associations of urinary sodium excretion with cardiovascular events in individuals with and without hypertension: a pooled analysis of data from four studies". The Lancet. 388 (10043): 465–75. doi:10.1016/S0140-6736(16)30467-6. PMID 27216139.
On physical examination, hypertension may be associated with the presence of changes in the optic fundus seen by ophthalmoscopy. The severity of the changes typical of hypertensive retinopathy is graded from I to IV; grades I and II may be difficult to differentiate. The severity of the retinopathy correlates roughly with the duration or the severity of the hypertension.
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Recurrent headaches: Headaches are fairly common among people with or without hypertension. Some people with hypertension notice changes or worsening of headaches when medications are skipped or when the blood pressure becomes higher than usual. Headaches associated with hypertension can be mild, moderate, or severe and can be of a throbbing nature.
Unchecked, high blood pressure can lead to a myriad of serious health problems, such as heart attacks, strokes, and other forms of heart disease and kidney disease. It is extremely dangerous during pregnancy because it contributes to devastating and even deadly problems for moms and babies. Other impacts of hypertension include vision problems and sexual dysfunction.