100 bucks at the courthouse with the right woman

choose better

Can you buy dresses at Costco now?

that sounds like a good time

I was wondering the insane number of hotdogs or how erotically you ate them until I remembered "people watching" is a term. (Or do you lady and tramp it with the dogs?)

Unironically my first official date with my wife was a Costco trip.

If you go to a fancy enough restaurant and pay for both people, it's quite possible to spend three digits. And for some people that's fine.

But if you can't afford that, you shouldn't do it and if someone expects it of you, fuck that person. Find you someone who's happy just to spend time with you regardless of how much money you spend, if any. There are people out there to whom the effort you put in to spend time together matters more than any attempts to impress them (particularly with money).

And even if you can easily afford it, don't do it on a first or even second date. You really want to get to know a person before they get any hint that you're doing well. It's very easy to run into golddiggers otherwise (and that doesn't really depend on gender either - tons of male golddiggers out there too).