Can one diet for too long?

I started counting in March. Due to lack of knowledge about nutrition at the time, and being pretty much an expert in it now but not applying the rules myself, I've spent some of those months way under my recommended intake. I've spent about two or three days at my maintenance level, but got scared and gone back to dieting. I was thinking about stopping this month, but I was extremely nervous about it. I'd miss this too much, and my obsession with counting would find some way of continuing anyway. I'm not one of those people who doesn't count and ends up consuming heaps, in fact it works the opposite way- I'll end up getting curious the next day, and upon logging the previous day's food, wil be surprised to see how few calories I ate. I really don't know. Psychologically, it's very hard to eat at maintenance, and I need to know my breakdown.

I've got my whole family eating healthily, tell everyone that everything is good at the right balance, not to restrict themselves and that doing so will lead to failure, NOT TO DIET WHILE ONE'S STILL GROWING, and everything I've learned here- but the opposite of what I do.

Also, if any of you remembered me from before, I said I was 5'5"... I recently measured myself and found I'm actually 5'3", if that changes anything (it certainly had me bummed) and 132 lbs.

"Do or do not.  There is no 'try' ".... Yoda... The Empire Strikes Back

In other words, sometimes you have to stop evangelising about knowing what to do and just get on with it.  Go with a reasonable maintenance intake and stick with it for at least two weeks rather than bottling it after a couple of days.  Work out how to get the correct intake and make developing your new eating habit your new goal.  Persistent undereating makes you more likely to gain weight.... but you know that already.  

I just recently had to stop dieting, because i was getting myself sick. My Doctor had put me on a 1000cal diet for the past 3 weeks, and I was always tired, grumpy, cried for no reason and my muscles were hurting like crazy. Tho i was eating enough protein, and muscle training twice a week, i was loosing muscle mass - my massotherapist scolded me. I work full time, go to the gym twice a week, dance lessons another twice a week and walk my dog 30mins everyday. I was just eating way too little for what i was doing! So i stopped. Im not counting right now, and i just may try tonight to enter what ive been eating but im assuming im eating more 1300-1500 and maintaining. Dont discourage yourself, listen to your body. Mine told me to stop. I will wait till after my wedding to strart again, give it a rest! Oh, and when i stopped i gained a pound in one week, but lost it again, probably cause im still eating less than the energy i burn. Now im maintaining so dont freak out if you gain back the first week!

Thanks for the advice.