About once a month or so, friends and I will hit up a nice restaurant in San Francisco, and it probably averages about $75 to $100 per person by the time we count appetizers, entree, dessert, and coffee. My friends are really into wine and they always bring a very nice bottle, so although we do have to pay for corkage, we're not actually spending big bucks on wine from the restaurant.
The most expensive meal I've had was probably at Cyrus in Healdsburg, CA. They've since closed, but at the time we visited, I believe they had two Michelin stars. That was truly a "destination" meal, and was incredible. I think my portion was around $120, but can't remember for sure. It was definitely worth it, but being so extravagant, isn't something I would do frequently. Maybe once a year or so.
Food aside, the most expensive bottle of wine I've probably brought to a dinner was around $350. The same good friend of mine had just gotten a new job, so to celebrate I brought the wine that time, and found an older vintage of Silver Oak (Napa cab). Again, not something I'd do often, but for a special occasion, it was fun for us to share that.
Couldn't eat or drink that way all the time. But it's fun to inject a nice dinner once a month or so into an otherwise pedestian course of fast food and mac 'n cheese