Pink Daisy - I do something similiar, though I don't plan my calories quite like that. I just kinda eat what I want within my calorie range each day.... which would be between 1400 to 1900. I don't plan it by calorie amounts... I plan it by what I want to eat that day then see what I come up with. As long as it stays in that range, I'm happy. I also do free days once a week, and usually use it for going out to dinner with friends or family (or even the occasional bar night)... but if I don't go out out, I typically still count my calories and stay in that range. So, for the most part, I typically have like 2 days a month where I go out and eat without really watching the calories and eat really horrible naughty foods....

hehe It seems to do okay for me, I've been losing pretty well and consistently. I don't know how long that will last the more weight I lose, but for now it's okay.
I'd suggest that maybe 1 or 2 days a month you allow yourself to have that free meal.... as compared to a free a day.... and then the other days you try to at least eat healthy (even if you are at a restaurant, i.e. lean meats, veggies, simple foods, etc). And if you go out more than once on your free day.... pick a meal that will be healthy and the meal that will be the actual cheater.
Just my suggestions though. It works for me!