I never cheat per se, but I do allow myself to eat driven by satiety for the most part; thus, the palatability and calorie density of what’s on my plate naturally dictates how much I’ll eat. Bland whole foods in limited variety? I’ll “intuitively” stop at a sensible amount, roughly corresponding to the maintenance requirements of my current mass. Deep-fried foods accompanied by a colorful constellation of complex heavy sauces / dressings, a vast selection of appetizers, alcohol and sugar-ladden dessert? My “intuition” will expose me to risk of (massive) overconsumption. And that’s fine a few times per month, in fact necessary for maintenance, so long as tightly budgeted and monitored, or rather promptly I will be held accountable by my scale.
Example (simplistic but kinda within reason): I mainly practice OMAD. At my current weight, my TDEE is estimated 1,900 kcal/day (in practice I strongly suspect that it’s greater because of the effect of OMAD and my prioritization of whole foods, but let’s keep this simple). Before weight loss, my TDEE used to be estimated 2,300 kcal/day. Assuming that on my regular food choices I’d end up eating 1,500 kcal/day on average, what would my “budget” be if I wanted to overeat on 3 occasions per month without compromising weight loss?
Answer: To still progress toward my “current” weight to-be (note: eventually progress would become asymptotic, meaning that it would take virtually forever to lose the last few pounds or kilos, but again let’s keep this straightforward), I’d have to eat no more than 1,900 kcal/day on average, or 57,000 kcal/month on average. Since I eat 1,500 kcal/day or 40,500 kcal per 27 days, this spares (57,000 - 40,500) = 16,500 kcal for the remaining 3, or 5,500 kcal per “feast meal”.
Again, I don’t do such mental gymnastics in practice, but my experience suggests that 3-5 ad libitum restaurant meals is what I can afford each month without jeopardizing progress or nowadays maintenance (at proportionally reduced intake).
Be careful cheat meals are deliberately counter-productive.
Every other Sunday I have a Dungeons and Dragons campaign and the DM buys everyone these huge awesome bacon cheeseburgers and fries from the local pub - that’s my cheat meal.
But it’s once every 14 days, not two times out of every seven.