When an off program/cheat meal becomes a cheat day

I am an all-or-nothing person, so I definitely relate to this. You are definitely doing the right thing by planning your meals to manage it. What about making sure you get a workout in on those days? That would help mitigate the CICO balance, and I know working out makes me automatically more aware of how hard I have to work for it, making me less likely to binge later on.

Ultimately, it's tough but you have to decide what's important to you. I had a work trip last week, and I knew I wasn't going to be able to stick to my calories. I allowed myself the week to enjoy the food without worrying about it, but not go too overboard - I didn't count calories, but it also wasn't a complete free-for-all. I knew that I would gain weight and my long-term weight loss would be slower, but I accepted that consequence and now I'm not beating myself up as I work to lose what I gained. All you can do is make the best choices for you, and remind yourself to set boundaries that you will hold yourself accountable to keep. It isn't easy, and I have failed at times, but the more I remind myself that I can do it, the better I do. And when I do allow myself those meals, I enjoy it a lot more than when I just let myself eat mindlessly.

Gosh reading this I'm scared about how to handle a whole 7 days in Orlando on holiday/vacation
I'm just planning to eat light in the day and enjoy the evening meal as much as possible (avoid fried and creamy dishes) plus eat back activity calories earnt.
If I put on (highly likely) I am confident that I've now got the tools to lose it

Don't panic, this situation is life, just deal with it as best you can, there's no finish line or timer

I think many people feel this way, especially in the beginning. And a lot of people quit the whole idea of being healthy because of it.
But I would hope people are losing weight to be healthy, not just to lose weight. The "it's not a diet, it's a lifestyle change" has to be true for most, because that's where the success is most often (if not always) found.

It's a tough challenge to take on, but please don't feel guilty or sad about food. Learning to say "I ate this, but it's okay" is so important. Food is fuel. Sometimes the fuel isn't optimal, but that's okay too. Your body is this truly amazing thing and it can handle it.

I personally get the initial "oh no, they want me to eat" reaction when someone invites me over. Then my rational thought has to come say "that's okay, just breathe", but I also start thinking about what I can do to make it work for me.
I can load up on veggies, have one bread roll instead of three, drink plenty of water before dinner, enjoy conversation more so my body has time to tell me it's full, etc.
If you're eating out (which I rarely do, living in the middle of nowhere), you can ask for spesifications to your meal, like dressing/sauce on the side or maybe salad/veggies instead of fries if that works better for you.

Regarding the aftermath of already having had "too much" or "something bad", I want to urge everyone to think rationaly about it. So what if you had 200 calories more than planned? Nothing bad is gonna happen and you shouldn't beat yourself up over it. It's okay.
If you have a whole meal, dessert and three drinks in "excess", it's still okay. You might be feeling physically ill at this point and a little tipsy, depending on your tolerance, but you still shouldn't feel guitly about it.
When you have a moment, sit down and assess the situation. Look at the facts (like how much you need to eat to gain a pound).

A little something is still just a little something. A lot of little somethings might become a big something.

Sorry for the long post. I'm rooting for all of you cause I know you can do it!
Also one of my favorite quotes: "Ever tried. Ever failed. No matter. Try again. Fail again. Fail better." - Samuel Beckett

That's why I log everything, doing the math helps, and seeing the big red numbers and figuring out how much I'll GAIN that week definitely helps.

Try not to feel too bad about it. Depending on your height etc. 2000 might even be maintenance, and it's only 3 days

I have to plan the cheat out pretty carefully. It needs to be out somewhere, so there is finite end to the meal otherwise I am capable of stretching a meal out for many hours; and I plan in advance what delightful indulgence I will partake. I've been known to spend a lot of time perusing menus online to decide what I will eat...and I like it to be REALLY AWESOME. Like braised short ribs with butternut risotto, and some really good bread...that was a fabulous cheat.

My regular weekly cheat is going out to a really good ice cream place and getting ice cream on Saturdays. The short ribs were a once a year birthday cheat.