A restaurant that doesn't have that info listed on their menu or website?

*find a chain restaurants matching menu item and log that. It's not perfect, but it's better than nothing.

• Carnivals, festivals, food trucks, street fairs, etc?

Same answer as above

Family gatherings or parties?

Estimate/guess/log similar items

Meals with multiple courses? Just log all the courses, guessing to the best of your ability. If your log isn't exactly perfect, so be it

Some shots while out drinking? (I drink occasionally).

Assuming these are straight shots, just log 1.5-2oz of whatever liquor you ordered and only drink 0 Cal chasers.

I've thought of just trying to eat half of an skip the appetizer if I'm going out to eat, or having just a single plate of food if it's at like a family gathering or festival

I'm sorry boo but pre gaming your food with more food, or having multiple plates is just not conducent to 1200 calories. The biggest part of dieting is just learning to say no when you wanna say yes. But cheat days are a thing so it's not all doom and gloom!!