1) Don't wait until the fall, when your leader seems to think it'll get "easier" to avoid the things you love. No matter what time of year we're in, it is easy to think that the weight loss will come easier any time other than NOW. Do not listen to these thoughts - when that later time comes you'll wish you had started NOW.
2) WW is incredibly flexible and there is no need for it to get boring. Many people lose weight successfully without ODing on fruits and veggies, though ideally you will follow the 8 healthy guidelines WW provides and get your servings of fruit and veggies in there somehow.
You
can develop strategies for eating out and staying OP, but it will be difficult and it takes a tremendous amount of willpower if you are not using to denying yourself anything. WW is only restrictive in that most of the things you find in restaurants shouldn't be consumed by anyone to begin with (who needs a 2,000 calorie dinner??), it is only restrictive in that it asks you to eat sensibly on a regular basis.
I am a huge supporter of not depriving yourself of anything. If you do, you will resent the lifestyle change and give up. Just make sure that you balance out the indulgences with a good dose of moderate, healthy eating. Instead of ordering in a whole pizza, go out to a pizza place that serves by the slice - have a slice of your favorite pizza, savor it, make it count, and adjust the rest of your day to accommodate those points. Going out for Mexican is totally doable - I make sure nothing is deep-fried, covered in cheese, guac, or sour cream, and wrapped in a corn rather than a flour tortilla. Works like a charm, I always come out on the other side feeling like I made good choices. It can be done, but it takes commitment and perseverence.
Good luck