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One of the reasons I dread having a first date is because typically they are like job interviews.  You have to get to know someone, just like you do in a job interview, so you ask them 21 questions about themselves.  After thousands of dates, you can imagine how boring this can be, both asking the questions, and answering them repeatedly without an end in sight.

One of the things I tried recently to shake things up a bit and make a first date more interesting was to switch up my questions. Here are some examples of questions you may have asked or have been asked, and what I think you could ask instead to make a first date more enjoyable:

Generic Question: How many brothers or sisters do you have?

Better Question: If you have any siblings, tell me about one of the funniest moments you remember with them?

Generic Question: What do you do for a living?

Better Question: What’s the favorite part of your job?

Generic Question: Where did you go to college?

Better Question: What did you major in college, and if you could have changed your major and done something else, what would it be and why?

Generic Question: What are some of your hobbies?

Better Question: Which hobby do you prefer the most, and why do you like it so much?

Generic Question: Do you have any pets?

Better Question: If your pet could talk, what are some of the things you think it would say to you?

Generic Question: What’s your favorite food?

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Better Question: What was the last thing you cooked, and why did you enjoy preparing it?

Generic Question: What’s your favorite movie?

Better Question: What were some of the last few movies you watched, and did any of them move you at all?

Generic Question: What’s your favorite band?

Better Question: If you could listen to any band dead or alive right now, which would it be and why?

Generic Question: Where are some of the places you’ve traveled to?

Better Question: Tell me about the most memorable moment you’ve ever had in a foreign country.

Generic Question: Are you close to your parents?

Better Question: Tell me about something about growing up with your parents that you remember vividly, funny, sad, or just a cool moment.

Generic Question: What do you do in your free time?

Better Question: When you have free time, what do you usually do more: relax, read, listen to music, watch movies, engage in culture, seek out adventure, or all of the above?


I can go on and on with these generic questions that don’t get to the core of what will show if there is a match. Personality and chemistry reign supreme, but these generic questions don’t target those characteristics. So hopefully my “Better questions” will help those of you who are going on yet another first date.   When you ask someone these questions, take extra care to look at their facial expressions, so you can see how they got surprised and/or intrigued by your question.

I think these questions will give you more of where the person is coming from.  Whether or not they are creative, funny, or if they can think on the spot.  Plus, based on the answers, you might find that their personality is a lot like yours if they choose some of the same answers you would choose. Of course it’s only fair that you answer them also, so make sure you thought your answers through. In the end, this would be a much better way to get to know someone in my opinion while walking in a park with a coffee or an ice cream in hand.

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