First off, lifelong deprivation is no one's idea of a good time. If you really love a particular/specific food that you have placed on your "No List" and you haven't found a decent substitute, then you might want to consider letting yourself have IT once in a while. I was an ice cream junkie, but I am really satisfied by coconut milk ice cream. It has the flavor and mouth feel that works for me. However, nothing can mimic a Duncan Hines brownie made with eggs and oil and a box of chemicals. That fudgie square of heaven just cannot be made in the sugar free, wheat free world in which I live. I don't buy the mix and I hide from dessert tables.
Second, you have got to bloom where you are planted. If you already have an extensive and informed "No List", I bet you already get a fair amount of bullshit from your friends when you go out to eat or pull out your nuts and apples at a gathering. If you are in New Orleans and want a beignet, have one. When faced with a rare and/or local delicacy, participate. If Nonna is making homemade manicotti, have some. Just don't gorge on it and try to get some fruits and veggies in you at the next meal.
Holidays are not reasons to over indulge. In the US celebration food has, for the most part, become easily obtainable. Turkey and stuffing, pies, cake, roast beef, etc can be found at any restaurant. These foods are no longer special occasion foods, unless Tuesday is now a special occasion. If you are going to go for IT, make IT something you really enjoy.
Third, I am betting, from personal experience, that if you haven't had IT in a month or so, chances are you are going to be very uncomfortable when you have it. This past weekend I had wheat for the first time in 6 months. I promise you, I won't do that again anytime soon. But, that biscuit top was delicious. I am terrified of eating dairy. I haven't had it for a very long time and I have convinced myself that one trace of brie will wreck me.
Once you decide to have IT. Enjoy IT. Don't obsess about IT. Don't feel guilty about IT. You had IT and at some point you'll have IT again.
I guess what I am trying to say is indulging once in a while is ok. Give yourself permission to be human. Just remember to keep treat foods from becoming trite foods.








