Check out these calorie-boosting tips for helping you get to range: www.sparkpeople.com/resource/nutrition_art
It's true that listening to your body may be what got you overweight in the first place - but remember that means your body doesn't send/interpret those signals correctly. So why listen to it now and eat less just because it doesn't think you need it? It was wrong when it said "eat more", and so you got fat. Maybe it's wrong now, too.
Your body needs fuel. Being 500 calories short is a LONG way short. That's likely to be very unhealthy and you should do what you can to try to get into range more often. If it feels weird now, it'll begin feeling more normal as you get used to it.