Might be a good idea to make simple food plan of meals you make, the normal idea would be test before meals then 1hr and 2hr post meals, I also test pre and post exercise and look for trends current trend for me is a high BG post workout for a couple of hours, tweaking my smoothie ingredients by substituting in protein powder for a banana worked yesterday.
I increased my overall testing in January after changing my diet in November, then I joined a gym at the beginning of this month, which then added more testing, so Ive been testing 10-15 times a day as the variables are so great, it's been an evolving process over the past 3 months and continues as I include and exclude different foods.
If a meal or individual food spikes me, I will either exclude or retest it another time, or try lowering the offending portion size.
Snacks I now know, through I can get away without post testing, such as berries and thick double cream, Brazil nuts these are my go to indulgence.
My last meal last night, I tested 5.4 @8pm I then had a meal half an hour later 2egg cheese, onion, mushroom omelette cooked in a good portion of olive oil, followed by the double cream and berries. BG 5.9@2:30am.
Good luck
Edited too add...9 times out of 10 its painless, just rotate which fingers you test with, set the lancet to the lowest setting that gets you blood, also check it hasn't moved to a higher setting accidentally before use.