Good Questions To Ask A Date

Men's Dating

6 Good Questions to Ask to Really Get to Know a Date

Hunt Ethridge

Written by: Hunt Ethridge

Hunt Ethridge

Hunt Ethridge is the co-founder and CMO of the as well as senior advisor and board of directors at other firms.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Dating is a mix of biology, sociology, psychology, and anthropology. By definition, so is everything we do, as these are the four tenets of humanity.

I mention it because it’s good to focus on the different aspects of dating, so we can better understand our motivations, society at large, and the person sitting opposite us. Once we start to understand why we do things, it’s much easier to figure out how to do things.

For example, we, as a society, have made a sociological agreement on dates to run through questions like a job interview. “Where’d you go to school?” “Do you have family?” “What do you think you could bring to a relationship?”

These are all logical, boring questions that we all have asked and been asked a million times. These questions don’t showcase who you are in any way or offer any insight into the other person.

So here are some better questions that should help your personalities come through.

1. If You Could Do Your Passion/Hobby as a Job, What Would It Be?

Instead of asking a date “What do you do for work?” or “What do you want to do for work?” ask them this question. When you do, you’re going to hear what they are really passionate about. Not what they think will be a good job or what their parents may be pushing them into.

Working two minimum wage jobs is not who they are, but knowing they do ceramics on their own time is.

2. What’s One of Your Favorite Childhood Memories?

Knowing where your date grew up will help you understand where they came from a little bit, but it doesn’t lend itself to larger exposition. You want your date to be able to tell you happy stories.

If you ask “What’s one of your favorite childhood memories?” you’ll not only find out where they are from, but what type of experiences they had growing up and how it turned them into who they are.

Photo of man thinking

The way this question is worded, it’ll get your date thinking about happy times in their life.

For example, your date saying they grew up in the country is a good start. But did they grow up farming? Were their parents writers in a little forest cabin? Was it on a large horse-riding property, or was it in a small trailer near ATV and snowmobile trails? Did they enjoy this time in their life? These are the things you want to know.

3. Which Holiday Did You Get Most Excited for as a Kid?

Unfortunately, not everybody has/had a good family life. While you may love your family and have lots of fond memories, others have left abusers, broken families, bigots/racists, and addictions.

While asking about their family may seem innocuous, it could unintentionally lead you down an emotional rabbit hole, inadvertently making the other person sad or anxious.

Instead, you want to ask a tangential question that will allow them to bring their family into the conversation if they want to.

They may say, “My family had a great Passover tradition in which my extended family would all stay at my house. It was so much fun but so crowded!” Then you know that they probably have a good relationship with their family, so you can start asking more questions.

On the flip side, they may say, “I really loved Halloween. My mom wasn’t around, so my grandparents always took me trick-or-treating. They couldn’t really afford the nicest costumes, so we’d get the cheap plastic ones. But I loved every minute of it.” Now you know that you may want to tread lightly with your follow-up questions.

4. What’s the Best Meal You’ve Ever Eaten?”

“What kind of food do you like?” is a fairly common question, and there’s not necessarily anything wrong with asking it.

But it just lends itself to possible negative connotations and the person listing things. “Oh, I like Chinese and Italian usually. Really don’t like Indian. Too spicy.”

Photo of burger and fries

The answer you get from this question should lend itself to good follow-up questions.

Again, not horrible answers, but there’s not really a lot to go on here, and now your date is thinking about meals that are too spicy.

Asking “What’s the best meal you’ve ever eaten?” is not only going to tell you some of the types of food your date likes, but also whether they travel and are adventurous, or whether they have culinary traditions in their home, etc. “Oh, man, I am not that big of a meat eater, but I was visiting a friend in Kentucky, and we went to a barbecue restaurant. Let me tell you, the ‘barbecue’ that Northern people think of is nothing like what it is in Kentucky!”

5. What Do You Look Forward to the Most on Weekends?”

This is just a tweak of verbiage. Asking “What do you like to do on weekends?” usually prompts the same, overused type of response: “I am happy at home watching Netflix or hitting the bars on the strip. Love seeing my friends and family.”

This is the beige of answers. It gives you nothing. However, if you ask “What do you look forward to the most on weekends?” not only are you going to find out what they like to do on the weekends, but what and how they say it will give you some insights into their personality/life.

“What do I look forward to the most?! Sleeping! I just finished my doctorate, and I am so sick of having to work on it during the weekends. If I could, I would just sleep until noon until I catch up on about two years of sleep.”

6. What Future Fantasies Do You Have for Your Life?

“Do you want kids?” is a normal, relatively important question, especially as we get older. But it doesn’t really open the door to happy, fun conversation.

It could trigger ticking biological clocks, reticence from men, negative childhood experiences, etc. Again, it might not, but you want to give yourself the best chance of good, fun, positive conversations.

However, if you ask them how they envision their future, you’ll find out pretty quickly their thoughts on kids.

Photo of happy couple

The wording of this question opens the door for an uplifting conversation.

“I just want to backpack through Kathmandu and Nepal, live off the grid, and maybe travel up the Amazon to do charity work.” This means your date is probably not thinking about kids.

“I’d love to live in the country. Maybe have some horses someday.” This means your date may or may not be thinking about kids.

“I was a foster kid, and I completely love my parents for what they were able to do for me growing up. I would love to give back someday myself.” This means your date is leaning toward wanting to have kids.

Ask Questions That Gently Steer Your Date Toward Personal Answers

You don’t want to grill your date. You want to ask positive, emotional questions that get them to open up about themselves, so you can get to know them.

Every question you can ask logically, you can ask emotionally. So try and think of ways to translate your questions. “Oh, what’s that ring you’re wearing?” vs “Tell me the story of how you got that ring!”

Also think of questions that help people recall happy times. “When were you most comfortable?” “What’s the best advice you’ve ever given/received?” “What’s your proudest moment at work?”

The goal of any relationship is to make each other feel good. When you do that, your dates will want to tell happy, personal stories. You’re getting them to access their emotions or, another way to put it, you are creating chemistry!

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