It's a cliche to ask a woman, "Do you come here often?" If however, you're trying to get this woman riveted in you right from the beginning these are the types of questions you should be avoiding. Any question that needs a yes or no answer is going to create a silence. That silence will grow into something that will have to be broken with another uncommunicative question.
With a inquiry as atrocious as that one you'll also be lucky if she can be bothered to answer it. You could even get a sneer as she turns her back on you.
The perfect beginning to any communication is an open ended question, it's a question that creates more questions from its answer. Instead of starting your question with a do, start your question with where, what or how. This forces her to answer the question with a real answer as an alternative to yes or no. This can then lead to another question if the answer offers you that opportunity.
Instead of using the do you come here often line, you can get some conversation going with something else.
If you can see your potential date isn't enjoying herself as much as she could be, you can ask, "how often do you come to this dump?" If she really isn't having fun, not only have you asked a great conversation starter but you've shown you're paying attention, and know exactly what's going through her mind. This type of question also throws a bit of humor into the conversation straight away.
If you're beginning to get on with her you can propose a more exciting place for your first date.
If you start speaking with women regularly you will learn naturally what type of open ended questions work for you, and what questions need to be avoided. Once you get your questions ready before you start speaking you can have the next questions ready for the variety answers you get.
Communicating successfully with women does take a bit of practice if you're not used to doing it on a regular basis. It can be a challenge sometimes especially if you have the outcome in your head before you start chatting.
The more experience you get the better you will become, and the questions will sound a lot more natural. This stops them looking like you're struggling for questions just to create a conversation.
A lot of women will get approached by men every time they go out, especially if they're stunning. Learn to understand what the woman wants in the conversation. Have a different approach to what 90% of men do when they just try to impress her. Show an interest in her, and talk about the topics she likes to talk about. This is a quality you'll understand more as you gain experience, but the more you go out of your way to understand these things the more successful your dating will be.