Dating is about getting to know each other.  Of course, you share about yourself.  And you also ask questions to get to know the other.

These questions should be discussion starters, not interview questions.

It’s not only what you ask about, it is also how you word the questions.

Ask bold open-ended questions that help you get to know the person beyond the things that they do.  

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?”

Ask for past stories (‘what did you do’), not hypotheticals (‘what would you do’).

“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.

Additionally, in answering a hypothetical question, the responder can answer what they think is the right answer. It is harder to fabricate a story from the past.

Avoid leading questions, questions that suggest a particular answer that the questioner desires.

Leading questions usually include words like:

• “You were helping out, weren’t you?
• “You didn’t refuse to help, did you?
• “You were helping out, right?
• “Isn’t it true that you were helping out?
• “Weren’t you helping out?