HI Tittemonster, As you know by now, losing weight is a strange strange thing. I wanted to shed some of my excess kilos last year (because of high blood pressure and general unwell feeling) and decided to count my calories. Invested in a Tupperware digital scale (expensive but worth it) . Took all my slimming books off the shelf, in particular you need a good calorie counter. For the first week I diligently weighed all food and counted calories - I put myself on a 1800 - 2000 per day calorie intake for starters. By the second week I was quite used to the counting and stopped weighing everything - I tried to err on the "good" side and not on the bigger portion side, gauging with my eye only. I then went down to about 1600 - 1800 calories per day. I ate anything I wanted as long as it was counted.
A tip: I would see my calorie allowance as a purse filled with allowance -money - Question; do I want to spend my allowance on this piece of chocolate cake or rather on this huge plate of chicken stir fry? We will all answer differently but I quickly learnt what kept me feeling full and what made me want to eat, eat, eat.
I managed to shed 14kgs over the next 3 months and have kept it off ever since by "calculating" (without scale) before I eat.
I am thinking of maybe starting up again and try and shed another 10kg at which point I will not bother to shed any more (I think). For interest: I also gained my weight when I was pregnant - 29 and 26 years ago.
All the best with your efforts - the library has a good stash of calorie counters etc. 