All dating guides declare the importance of asking open-ended questions. They are essential for making the date flow and showing that you are interested in her. Furthermore, they allow her to talk about her favorite subject (herself ) instead of listening to your football stories.

The beauty of open-ended questions is that they encourage full responses rather than brief yes or no answers. Think how different the conversation would be if you asked ”Why did you study English?” rather than "You studied English, right?" The former leads to an actual conversation about what she wants and what she enjoys, while the latter invites a simple one-worded “yes” response.

To engage in a successful and interesting first-date conversation, take note of the points below. Don’t use these tips as a script, however. Once the conversation gets going, it should flow on its own accord.
Friends And Family
Question 1: "So, what do your parents do for a living?"
Question 2: "What do you and your friends do for fun?"

Talking about friends and family is something most people can do at length. Questions about these topics make excellent icebreakers, they're natural questions to ask -- not too personal or invasive -- and they easily lead to an in-depth conversation.

Listen to her answers and ask follow-up questions. For example, if she says she's from a large family, ask how often they all get together -- it'll often lead to stories of family weddings or Christmas parties. If you have friends in common, this is an easy place to start the conversation. Asking how she knows so-and-so, how someone in particular is doing or how a specific couple broke up can make for interesting conversation and can solidify the feeling that the two of you have something in common.

Just make sure not to dwell on the subject of other people for too long because it’ll prevent you from really getting to know her.
Career
Question 1: "How does someone get into that job?"
Question 2: "What do you want to be doing in five years?"

Other big icebreakers revolve around work. We spend most of our waking hours at work, so it's a subject everyone has much to say about. After the obligatory "What do you do?" question, the possibility for more open-ended questions is endless.

Detailed explanations of the job, her future career plans, why she likes/dislikes it, annoying colleagues, what happened at the office party, and what she would say to her boss if she quit will help you get a true sense of her personality.

Like talking about friends and family, however, try to use this just to get the conversation started. Although everyone could talk about work all night, we don't usually want to; we like to leave the office behind at the end of the day. Be especially wary of letting her moan too long about her job; it could make the date appear as if it was focused on negativity. Move on to something more personal and fun ASAP.
Hobbies
Question 1: "Why did you start horseback riding?"
Question 2: "What do you enjoy about helping the homeless?"

Getting her to talk about her interests and hobbies moves the conversation in the right direction. These are more personal questions and she'll enjoy talking about them.
 
If she has quite a serious interest -- like charity work, for example -- it can take the conversation above meaningless small talk, allow you to show your sensitive side and create the impression of a real connection. On the other hand, quirky hobbies, such as keeping reptiles, will open her up to some light and humorous banter.

More ways to keep her gabbing…In the process, keep an eye out for opportunities to arrange another date. Offer to accompany her next time she does an activity, or invite her along to one of yours if you think she'll enjoy it. At the same time, listen out for warning signs. A woman whose social life revolves around her church group is unlikely to be an easy pickup.
Spontaneous Topics
Question 1: "What's the worst outfit you've been out in?"
Question 2: "When was the last time you were that wasted?"

More spontaneous conversation can come from your surroundings. Using them for inspiration will give the conversation a less scripted, more natural feel. These questions are less likely to be of the standard getting-to-know-you variety, making for more interesting and fun talks.

If you're in a restaurant, ask what her favorite dish is. Again, keep taking the conversation forward by asking other related questions: Find out why it's her favorite, where she first ate it, how well she cooks it, etc. A drunk person in a bar might lead you to ask her what's the most drunk she has ever been -- in which case, you should be prepared for crazy college stories to follow.

These stories could be quite brief, so don't be afraid to push with more follow-up questions. Maybe offer little stories of your own to get the ball rolling, but don't dominate the conversation. While most of these questions are throw-away ones to fill dead air, they can lead to real conversations that spiral off on random tangents.
Growing Up
Question 1: "Where did you grow up?"
Question 2: "Any high school horror stories to tell?"

Other personal questions to ask are about her childhood. This can lead to more intimate talk. Most fun memories come from our childhood and we relish telling them, even to someone we hardly know.

Ask her where she grew up, what her school was like, who was her best friend as a kid, what’s her favorite family holiday... and obviously all these will lead to further questions. Again, the conversation will probably be to-and-fro as she asks you questions in return, but allow her to do most of the talking.

Clearly, if she reveals she had a bad childhood, don't pursue the conversation further. Don't end it abruptly and appear insensitive, but at the same time don't let it spoil the date. These issues may come up later on in the relationship, but not on the first date.
Dreams And Aspirations
Question 1: "What did you want to be when you were little?"
Question 2:  "Why do you write a journal?"

The most personal questions are to do with her innermost thoughts. Everyone has dreams and aspirations that are core to their being. Talking about them requires a certain level of intimacy, so don’t expect it to happen on the first couple of dates. But when they do come about, these conversations are the ones that create real connections.

Because these are such personal things to talk about, she may be coy at first. Throw out examples of your own to encourage her ("I wanted to be an astronaut! Come on, you must have one?"). Most people have ambitions they define themselves by, but don't immediately talk about. Finding out if she wants to write a novel, sail around the world or work with chimps is essential if you want to know about the real her.
Making Chitchat
Open-ended questions are essential for dating. You'll use them all the time in normal conversations, but in the heat of a date, you can find yourself struggling. Remember some of these suggestions and you’ll find her spending the whole night talking away and thinking: ”What a nice guy. He's actually interested in me.” Listen to her and bounce questions back from what she says.

There is one closed question you should use, however: "Can I come in for coffee?"