There are a ton of questions that could be unique for your situation and in fact there are a series of pages devoted to that on GirlsAskGuys. I have selected a few from one of those lists;
*What did you last read, a milk carton, an encyclopedia or something in between? *What did you laugh at most recently? *What's the best piece of advice you've ever received? *On a scale of 6-to-47 how organized are you (or keep it simple, like 1-to-10)?
(working chick) What do you do? Is that what you've always wanted to do? What did you really want to do? What happened? What do you do when you're stressed? What do you usually do after work?
(College chick) What school/Major? Is that what you wanted? What do you like about it? What do you not like about it? Do you already have plans after you graduate?
(Random) What are you drinking? Do you like --- ? What do you do for fun over here? What do you do for fun over there? What do you think of the the chinese gymnastics? (olympicS) Do you think Phelps is hot? DId you know his body is like a fish? (olympics) What do you think of Russia and Georgia? Have you seen The Dark Knight?
Or, just try to ask questions that don't end with "yes" or "no", unless you have a follow up question for it.
Ask her just about anything, and if she finds you interesting she will make the conversation flow no matter what. Ask her about favorite movies, hobbies, favorite subjects, family members. You name it.
Best way to a woman's heart is actually crack a joke not really prank jokes but just be funny most girls love funny men and when girl seems to laugh at you she will actually starts asking other questions or starts the conversation..
Just be funny and joke around with her. Just like megcarr22 said...ask her about herself, her family, hobbies, about her weekend, how she's feeling, about her childhood, anything, and once she starts talking, things will come up and it will come natural after that.
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