I did keto for almost a year, and it wasn't that bad. My wife lost 50 lbs and I lost 45lbs. 190 > 145 (I had to put on weight afterward). First of all, you can eat things you enjoy, and you don't have to limit your intake. Basically, eat until you're full. When you're fully in ketosis (~2 weeks) you'll naturally not feel hungry. This is what makes keto great because you're never in a situation where you're hungry (at least after a few weeks).

Eating out isn't as bad as you think when in that position. Get a steak with some low-carb vegetables on the side. You can still have blackberries and raspberries and if you really need to "cheat" you can find some deserts that are no carb. Although best to limit those types of sugars. Use an app / website to track carbs for the first few months.

Just remember you're either in ketosis or not. There's no such thing as a "cheat" day on Keto as going over carb amount can kick you out.