Well, 36 pounds in 4 months is 2-2.25 pounds per week. Probably doable, but will likely require being pretty on point for the four months. Do you have an event you are working towards?
Possible, but it's not really possible to predict. Even when you're on plan, your body may fluctuate and otherwise prevent you from reaching your goals. Time-based goals, for me, are counterproductive - once I said I'd lose 10 lbs by a certain date - when that date came, I'd only lost 9. Rather than being thrilled that I was 9 lbs lighter, I was disappointed that I'd "failed" by not meeting my goal.
After that, I started focusing only on goals that I can directly control - days in a row of eating on plan, exercise goals, training goals (5K by a certain date, for example), and other things I can acheive regardless of a number on the scale. And the scale WILL follow those healthy changes...just not necessarily as quickly or consistently as I'd like.
It is very much possible, especially if you are just starting your weightloss, when the weight tends to come off a bit faster. Aim for that goal, however, do not look at it as a failure and dont let it discourage you if it takes a little longer to reach. Goals are nice to have as a way to help guide you in the right direction. But alot of times we think we failed if we do not meet that goal on time. Don't let this happen to you.
Good luck, anything you put your all into, you can acomplish if you really want it.
if you are starting at 286lbs it's actually much more doable, the weight will tend to fly off at higher weights. how low calories are you going? don't go too low, and make sure you keep good fats in your diet and walk 1-3 miles a day (or more if you can handle it).
If you are totally committed, you can probably lose that and more at your weight and still be healthy. There are already a few Christmas Challenges sprinkled throughout the board, maybe join one to help stay focused.
I started at 333 and ate a 1200-1500 calorie diet and at the end of the first 4 months I had lost about 68 pounds. However, I did not "cheat" myself, and I counted every bite and logged it. Some people think my approach, (the no cheating part) is a recipe for failure, but I was just so sick and tired of being super-morbidly obese that I went into it full boar and never looked back. I wanted to lose weight MORE than I wanted junk food. I also was retaining loads of fluid and had terrible edema in my feet and ankles, so probably the first 20 pounds was water...which I was grateful to rid myself of!