Blood pressure readings fall into four general categories, ranging from normal to stage 2 high blood pressure (hypertension). The level of your blood pressure determines what kind of treatment you may need. To get an accurate blood pressure measurement, your doctor should evaluate your readings based on the average of two or more blood pressure readings at three or more office visits.
The guidelines also redefined the various categories of hypertension. It eliminated the category of prehypertension, which had been defined as systolic blood pressure of 120 to 139 mm Hg or diastolic pressure (the lower number in a reading) of 80 to 89 mm Hg. Instead, people with those readings are now categorized as having either elevated pressure (120 to 129 systolic and less than 80 diastolic) or Stage 1 hypertension (130 to 139 systolic or 80 to 89 diastolic).

The new guidelines note that blood pressure should be measured on a regular basis and encourage people to use home blood pressure monitors. Monitors can range from $40 to $100 on average, but your insurance may cover part or all of the cost. Measure your blood pressure a few times a week and see your doctor if you notice any significant changes. Here are some tips on how to choose and use a monitor.

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.

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:

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.
A nurse takes your blood pressure at your annual physical. The numbers are recorded and the checkup continues. But do you know where on the blood pressure chart your levels are? Are they healthy? Too low? Too high, meaning you have hypertension? If you have high blood pressure or are heading in that direction, you should know that hypertension is among the primary enlarged heart causes, and a major risk factor for heart failure.

She'll inflate the cuff to a pressure higher than your systolic blood pressure, and it will tighten around your arm. Then she'll release it. As the cuff deflates, the first sound she hears through the stethoscope is the systolic blood pressure. It sounds like a whooshing noise. The point where this noise goes away marks the diastolic blood pressure.
I just started using high blood pressure medication and purchased a blood pressure meter at age 72. what concerns me is that the BP readings I get have a very wide variance in. I measure every morning as soon as I wake up, while still in bed and prior to having any coffee. I take 3 or 4 readings. I have found that on any given day my reading can vary from 126 to 143 systolic and the diastolic reading from 68 to 87. this wide variance makes it very difficult to track trends. My questions are: is this normal? is my instrument possibly defective? How can my cardiac doctor make a decision to put me on life long medication based on SINGLE reading in his office?