1. Start with something you have in common.
If you met through a friend, at work, through an organization you both volunteer for, at a happy hour, gym, class you both are taking, etc., open the door with a common subject matter.
2. Don't make it the Spanish Inquisition!
That is a put-off. Ask casual questions about their friends, childhood, career, etc. Talk about your own family and friends, and then segue: 'What about you? Are you close with your siblings?' Talk about what you both like to do in your free time, and what gets you out of bed on the weekends. Note to self: If they speak negatively about their family, their job, or just complain in general, this could be a sign of a pessimistic person.
3. Check out the book 'If...' when you get a chance.
This has a lot of theoretical questions that are fun to play around with. It forces you to think about topics you may not otherwise bring up.
4. Rather than a question/answer format (which can be a little daunting if you're on the receiving end), talk about situations.
And then ask for an opinion about the situation. By having a specific instance in mind, you can read his/her reaction, and then discuss the reasoning behind the reaction. It's just another method of getting to know someone. For example: How would they react if they were on the way to an interview, or a birthday party and their tire blew?
5. Random questions.
Such as favorite kind of car, ice cream flavor, toppings on pizza, town you've visited, restaurants.. these will all lighten the mood and possibly open up the door for other topics of conversation. Not every question should be heavy, brooding, or intellectual. Your date might feel as though they are sitting in a debate rather than a date. Integrate the fun questions every once in a while to keep from feeling intimidated.
6. Don't dominate the conversation.
Remember to let your date to ask questions as well! He or she is trying to get to know you at the same time, so be sure to allow room for other questions. The questions they ask can also help you get to know a little bit about them.
7. Topics to avoid on a date.
The ex (a big no-no!), past relationships in general, and expectations for future relationships. Not only is there a possibility that he/she may not want to share the information, but the answers could wind up making the rest of the conversation uncomfortable. Instead, ask questions that help you get to know him or her as a person.
8. As he or she feels more comfortable with you, you can start to ask the weighty questions.
I.e., religion, morals, values, etc. Don't be general (such as 'What do you value in life?'). Rather, talk about particular situations, and ask how they feel about that subject matter. Does this person this little white lies are OK? Is he/she judgmental of other's beliefs and values? Are they law-abiding? Or do they not mind cruising thru the stop sign every once in a while? Are they honest? While everyone may do their best to present themselves as trustworthy and honorable people, you can find out the truth by asking about specific situations that may have occurred in your or their life. Past actions and reactions can speak very loudly—much more loudly than the words that come out of their mouth!
9. Sometimes you learn best from not talking at all!
When people believe they are being assessed, their answers are carefully calculated and worded. But take careful observation of their body language, how they react to certain situations (the restaurant is full and there is an hour and a half wait), and how they treat the people you encounter while out together. These are very telling signs of someone's personality.
10. Check out 'The Definitive Book of Body Language.'
This book will give you insight into the world of nonverbal communication, which can't be controlled! Most of us don't know how to read nonverbal cues, and this book covers the spectrum, from gestures and handshakes, to facial expressions and accessories.
11. How does this person talk about the people they know?
Are they negative, or do they generally have a good outlook on people? What kind of friends do they have? Are these people that they have known since school, or are they people they just met on a Friday night? How they talk about their friends is a good sign of what they'll think of you in the future.
12. Remember the game '20 questions'?
It's a game kids play to pass time. Play the adult version, where each of you ask each other questions until you have both asked twenty. Keep it a healthy mix of humorous and serious questions. And remember to only ask questions that you would feel at ease with answering.
" The truth will eventually come out, so just be honest."13. Always be yourself.
Remember that the truth is the easiest thing to remember! So when he/she starts to ask you the questions, answer truthfully. Don't try to be overenthusiastic about a topic that doesn't interest you, or pretend to know a lot about a subject that you don't know much about, or answer questions that make you seem better/wealthier/smarter or anything more than you are. The truth will eventually come out, so just be honest. And watch for signs that the person you're with isn't being truthful. Does he/she seem to like everything you like, or has done everything you've done, or dislikes everything you dislike? This could be a sign that they are just trying to impress or appease you.
14. Ask questions that require more than a yes or no answer.
Open ended questions will provide more of an opportunity to get to know someone’s feelings or reactions to a certain topic.
15. Don’t dominate the conversation.
After sharing your thoughts about a particular issue, ask, 'How about you?' And don’t drone on and on. Your listener may begin to tune out, which can definitely kill a date! And watch to see if they tend to take over the conversation.
Sounds simple but really, listening to someone is crucial not only in conversation, but in relationships in general. Keep that in mind, and watch to see if they give you the same courtesy.