OP, for your description I'd say New Orleans, and I say that as somebody who has lived in San Antonio, Houston, and Nola. Nothing against Dallas, but I find it kind of buttoned up/stuffy compared to Houston and Austin. The big D does have good 20s female talent though.
Anyway if you do New Orleans, the airport is a shithole. It just is. French Quarter is very overrated, IMO, and worth 1 night at most and only if you've never done it. You're going to want to explore Magazine Street and the garden district. Fantastic restaurants all over and also look in the Uptown neighborhood. I'm going to repeat here that the French Quarter is overrated and there are only a handful of places worth visiting (mainly restaurants). When I lived there, the only time I'd go there is when friends/family were in town and wanted to see it.
Originally Posted by
DetailsIM
*I consider midtown, heights, river oaks, all downtown lol
We've got a suburb person in our midst
To those of us in/near the loop, only Midtown could remotely be considered downtown