Casbeers on a thursday night usually has some decent live music. They have the best acts around, in a very small, funky little place. A real local's, musician lovers place. Try their enchiladas too. Might be a little too informal tho...and they only sell beer
There's also a cool place out on Scenic loop road/ Leon Springs area. Good food, good music (usually), nice little bar, called the "Scenic Loop Cafe." Call for directions.
Some people like The Cove, I've never been tho. I've seen everything from head banger bands playing, to solo acoustic shows listed.
Or, just try the riverwalk. They have a great acoustic blues player, Rusty Martin, playing at the Kangaroo Court there on a regular basis. Rusty is one of the best around.
Or go to New Braunfels. Gruene hall on a thursday can usually have some decent acts. There are tons more places in New Braunfels, than San Antonio...to just have a drink and listen to some "decent" music. I think Casa Verde in Gruene has Monte Montgomery playing acoustic live on Thursdays. Monte is the best guitar player right now in Texas...mebbe the whole country. And his acoustic show is one of the best.
I'm not talking about loud, rock/punk/metal type of bands in any of these places. I'm talking about good, local musicians...usually playing alone, or with small ensemble. Good music to listen to when your not talking...and not overpowering any conversation your trying to have either.
Check out the Weekender, or the Current for schedules.
The key, imho...is taking her someplace YOU will be comfortable and can have a good time in. If your not comfortable, and having a good time...she prolly wont be either.
I took my current girlfriend to McDonalds on our first date. She's still with me 5 years later. Go figure. Must be something in those Quarter pounders...with cheese.

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sorry, won't do it again.
