The whole point of dating is to get to know the other person – who they really are, beyond what they do and what they like.

To get to that, you should minimize the number of stereotypical questions, like “What do you do?” and “How was your day?” And “What do you like to do in your spare time?” You want to know more about the other person than what interests you both have in common. So you both like hiking, so you both like Chinese Fusion.  So you both visited the same fascinating people during the year you spent in Israel. Those aren’t crucial for a successful marriage. And most people don’t really like those types of conversations anyway.

Most people are way more interesting than they come across on a first date where all they talk about is the weather, where they went to school and the room they are in. They just need to be courageous enough to share more about themselves.  Even on a first date.

Ask bold open-ended questions that help you get to know the person beyond the things that he does.   Avoid questions that have one-two word answers, rather aim for questions that get a conversation going.  Better questions begin with the words “What?”, “How?” rather than “Who?”,”When?”, “Where?”

“What got you interested in computer science?”  “How did you get involved with Chai Lifeline?”  “What was it like for you to be stranded in that remote airport by yourself and you didn’t speak a word of the local language?” “What was one of the scariest things you went through?” “If you were given $100,000 to solve a community issue, what issue would you choose to address? What might you start doing to address that?”  “Whose work do admire? What about it do you admire?” “If you could change one thing about your post high school experiences, what would it be?”

And of course,  use these questions as discussion starters, not just a list of interview questions.

With discussion starters such as those, you can learn lots about a person – passions, character, personality, priorities, how they deal with life situations.  The real person.

Another important point: It is best to ask for past stories rather than hypotheticals. “When you went through that experience, what did you do?” rather than “If you ever got into such a situation, what would you do?” You can learn much more about who he is from his past, than his ideas of how he hopes he would respond in that situation.

Listen with real curiosity. Beyond the actual words she uses, listen into the tone of the voice and how animated she is as she talks about it. Tune into her body language and facial expressions as she describes whatever it is she is talking about.

In this way, you’ll get to met some truly interesting people. Even if the shidduch isn’t meant to be, the dates won’t be so frustrating.