I live about 20 miles south of Nashville but have lived all around since 1982. I even lived downtown for a time. I'm quite an introvert and wish I could list off tons of things to do, but I can't. You were very helpful in my Florida real estate post, and I'm at a loss to return the favor. There are a lot of new venues that have popped up, but I haven't kept up because no one wants to date a 50 year old with a face rivaling Steve Buscemi.
That being said, I can say that if you like rooftop bars, I highly recommend L27 at the top of the Westin. The Westin itself is also highly popular. Fair warning that this place is pretentious as hell. If you want a more quiet, cozy experience, try the Rare Bird on top of the Dream Hotel. It has two fireplaces at either end of a wraparound patio, very comfortably seating for snuggling, and a great view of the bridge. Food at the Rare Bird isn't all that remarkable, but it is a very pleasant experience. If you want a killer steak (and can get a reservation), hit up Bourbon Steak at the top of the JW Marriot. There is also another rooftop bar above Bourbon, but I have never been. There have been quite a few other rooftop restaurants/bars pop up over the past five years, but I'm not one to go to these places by myself.
If you want to max out pretense, then hit up the Gulch area and head towards LA Jackson and get on the list for another rooftop experience. If you're with someone who likes fruitier drinks, have them try the Frozé. The Gulch area is a highly dense area for night-life. Pins Mechanical is also there, which is a pretty cool place that has a lot of pinball machines, arcade games, and some weird bowling. Very popular. Virago is there too, for some good sushi, but there are some really good restaurants this whole area.
I have heard good things about this show, though. Never been myself.
https://www.hocnashville.com/