I wouldn't worry too much about why you decided to lose weight. The answer is likely a combination of your family, your boyfriend, and yourself. It's true you should be losing for yourself, but many of us have something external that triggered us to start. For me, it was my daughter's upcoming wedding. If I were comfortable at this size, I wouldn't bother, but I'm not, so the bottom line is that I am losing it for myself, and I intend to keep it off. I am already planning for maintenance, because as you discovered, maintaining your weight loss is even harder than losing weight. As for where to start, I calorie-counted for years and I yo-yo dieted for years as a result, because I couldn't keep it up long-term. However, some people can. Some people have been quite successful at counting calories for years. Others have done well with Weight Watchers. Others have success with programs like Atkins. This time around, I am doing a low-carb diet called The Slow Carb Diet, only I'm doing a modified version of it. I have a carb sensitivity, so this diet works for me. I don't count anything and I have one cheat day a week, so this diet is something I feel I can do long-term. And I think that's the key. You need to find what weight loss plan best suits your personality, your time constraints, your budget, your body. Sometimes it takes experimentation to figure it out. I wish I could come right out and say, hey, my diet will work for you, but I don't know that. We're all different. Check out the Diet Central section and read about the different plans and if you see one you like, try it. That's the best way to start! And by the way, I don't think there's a family thread here, but this one might be helpful: Dear (whoever)-Letters you wish you could send!
. Good luck on your weight loss and maintenance journey!