..Heck, even in your own example your first date was in a bar, which now a days is a dozens of dollars experience for just a few drinks..

Pro tip for anyone still reading this far down into the thread: If you've a hotel - like a Sheraton, Hilton or any higher-end lodging.. Check out their lounge. The cheapest drinks in the city I live in are at the hotels - they generally will price cocktails 35 to 50% lower than the bars and clubs in the area, simply to catch a little bit of the cocktails action.. (also the hotels all have beautiful lounges)

Last time I went to New Orleans I stayed in a hotel on the edge of the French Quarter and drank for one fifth of the price that the drinks outside cost. Got good and oiled THEN headed out to hear live music.