It's true that San Antonio is the place to go for cheap drinks. You'll find seedy bars on every other corner. While this can be fun, you might want to "raise the bar." First stop on your Alamo City bar tour should be Paramour. See the city from their glorious rooftop lounge while sipping one of their sophisticated cocktails. Plan on splurging on your date or friends, but it's worth it!
On par with Paramouris The Last Word for some craft cocktails and suave clientele in this speakeasy-esque bar in downtown San Antonio. For something a little different, check out Carmens, where you can often enjoy some live flamenco music and dancing. They also have a fantastic tapas menu, so go with an appetite.
If you're wanting a haunt that's a little more low-key, check out Alamo Beer Brewery. They have a great outdoor patio and make their own beer - nothing too fancy - just good brews that anyone who likes beer can enjoy. They often have food trucks serving up some grub, and live music as well. Located as it is right underneath the Hays Street Bridge, it's simply one of the coolest bars in town.