Tack me onto the list of boring eaters - fortunately or unfortunately (depending on how you look at it), I can be OK with eating the same things all the time. (I brought PB&J sandwiches to school for lunch practically every day from kindergarten to senior year of high school!!)
I have 2 or 3 breakfasts that I switch around depending on what I have in the house at the time, one delicious sandwich for lunch along with fruit and/or veggies (again depending on what I have at the time), and a handful of healthy dinners that I know how to make. I also keep healthy snacks in my cubicle at work for when I get hungry in the middle of the day.
It makes calorie counting much easier since my days all look fairly similar (fewer daily calculations, I can plan in advance, and I have a good intuitive idea of how much wiggle room I have for random snacks or other things that might come up).
Making it a habit seems to be the easiest way for me to stick with it. If I ate differently every day I would quickly get sick of having to work out all my calories. I also cheat a little bit and tend not to count things like gum, spices, mints, etc. just to keep my mind on the big picture... I know that doesn't work for everybody but it seems to be OK for me.
As for how many calories you should be consuming - you can calculate it based on your height/weight and how quickly you want to lose. A 3500-calorie deficit is about equal to a pound of weight lost. There are a lot of calculators online, e.g.
http://caloriecount.about.com/cc/calories-goal.php
Good luck!