Important Questions to Ask On A First Date

November 30, 2011  |  
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Going for a first date can be pretty intimidating for most people. Your mind may be overcome with fears and insecurities and you may be afraid of rejection, failure, saying the wrong things, and coming across like a loser. It’s important that a first date be fun, yes, but it’s an added bonus if you actually learn valuable information about your date.  It also helps to have some questions in the back of your mind so that those dreaded awkward pauses don’t creep up on you mid-date.  Check out these 7 questions that might help fill the void of the lulls, as well as expose important information about the stranger sitting across from you.

1. Who are your closest friends?

This is a nice way to begin since it allows your date discuss things in his comfort zone while not getting too personal. Also, the answer can tell you a lot about the kind of person he is. For instance, if his closest friends are all from high school, it indicates that he values loyalty in relationships and is wary of change.  Remember that quantity is not more important than quality so stay in tuned to how he talks about his friends and what he tends to do when they spend time together.


2. How many siblings do you have?

This question offers a safe way to know more about his family without sounding like you want to be part of it tomorrow. If he comes from a supportive family, he will probably tell you a good deal about his parents, siblings, cousins, or grandparents. But if he appears vague and wants to abruptly change the subject, then it would be best not to prod him more since he might have had an unhappy childhood.

3. Are you an indoor or outdoor person?

It’s good to find out on a first date if your guy prefers a weekend roughing it in the great outdoors, or a fancy dinner out on the town.  Knowing what kind of guy he is will give you insight into what he does with his spare time and what makes him happy.  If you are a die-hard hiker and enjoy trail mix and camping more than anything, you might be wary if he explains how much he hates getting dirty and sleeping in a tent. Being in a relationship does involve a lot of compromise, but it’s also smart to know what you’re signing up for from the start.

4. What are your work ambitions/goals?

Even though this may sound too much like being interviewed for a job, it will give your date a chance to talk about his professional ambitions and aspirations for the future.  Men tend to be the providers in the relationship, although this notion is slowly fading.  Try to gauge what kind of husband and potential father figure he might be depending on how he answers this question.

5. What are your pet peeves?

You may be surprised at the number of unexpected things that come out of this question.  However, knowing someone’s pet peeves can be a comical part of the date and give room for a couple laughs.  It might also expose deeper meaning of his likes and dislikes in people or his political views.

6. How do you spend your week, outside of work?

Knowing what someone does during non-working hours can give you an insight into his priorities. For instance, your date might put in a 40-hour week at work, but if he still has the time and energy to hit the gym three times a week, you know that health and fitness score high with him.  What people do with their spare time, and what little time that can be, is the easiest way to see priorities in action, instead of just hearing him explain what he values.

7. What are your life goals/ where do you want to be in 10 years?

Again with the provider factor, men will commonly list off career ambitions and job related goals here.  It’s women that typically include the family life and marriage in the mix.  Don’t be offended if he doesn’t express his want for a wife and 3 kids by 2022.  Either he might not want to freak you out, or he thinks that providing is the most important thing for his future.  You don’t want a man obsessed with money and no interest in family life either, but this is a first date and some people don’t open up as much as others. You’ve got a jackpot on your hands if career, and family life escape his lips after this one.

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