What type of place do you feel comfortable in; I've older friends who dig Hip Hop, Dance Music etc. and they enjoy themselves at a few Spots in NY and CT. If you're looking for the Cavern type of setting it may be best to find your ideal spot to just be yourself and coordinate your Cavern type meets there; no need to whet your chops and find there is no steak beyond that sizzle.
Now the gents who are offering thier advice I'm pretty certain would not only have the place in mind but themselves to fill in as your Cavern type tour guide.
If its a "flirt" thing, simply share what type of atmosphere is to your liking etc. If its a "XXX play" thing, simply allow yourself to go out with the advice givers and cap off a good night out with a great night in.