> The dinner + tip is going to cost $200. Parking is going to cost $50 - $100 if you go into a city.

Why are you driving into a city that costs $100 to park in and then to a restaurant that costs $100 per person if money is a consideration?

Go to a local restaurant. Go to one outside of that city. Do literally anything other than the scenario you described.

I guarantee that if you're near a city where you can find $100 parking, you can find 100 or 1000 amazing small restaurants that are affordable and interesting.

This is a type of defeatism where someone imagines the worst possible scenario, erases all other options, and then pretends it's a choice between the worst scenario or nothing at all.