as far as the $50 or more per person, that's probably every few months. As far as sit down places where you spend about $20 per person I'd say at least three times a month. The $50< a person places are pretty few and far in between, that is usually a steakhouse. I don't even spend $50 a person on sushi, probably closer to $30 a person.
The last one was a a Ruth Chris steakhouse, It was good, we each got a filet, creamed spinach, house salads the mashed potatoes and some fruit/ice cream dessert that was decent. Bill came in at about $150 for two of us not including tip. I ended up leaving a $50 tip, because the service was about as good as you can get and when they are that good I really believe in rewarding it. Honestly though for the money I'd rather have gone to a Brazilian steakhouse or one up in West Palm Beach called "the Okeechobee steakhouse" that place is pretty much the best steakhouse I've ever been to, it's just a long drive. The one great thing about it is they haven't re-decorated the bar since the 70's and the bar clientele is stuck in the 70's, it's like stepping through a time portal. The rest of the restaurant looks like any other steakhouse though.