5 Questions To Ask When Dating Someone

Matt Lillywhite

Photo by Davids Kokainis on Unsplash


How often are you lost for words during a conversation?

If you’re anything like my former-self, your response will be something along the lines of “all the time.”

Right? We all want to have incredible relationships and connect with other people on a meaningful level. But the problem is that we don’t know how to start.

It sucks.

Consequently, you overthink every message, response, and your mind goes into overdrive as to whether the other person is genuinely enjoying the conversation.

Throughout my life, I’ve found myself in the same position as you many times. But I’ve discovered that asking the right questions during a conversation is equally important as giving a meaningful response. In the words of Tony Robbins:

“Successful people ask better questions, and as a result, they get better answers.”

So below are several questions that have massively improved the quality of my conversations. Each one of them enabled me to generate meaningful relationships, and I hope they do the same for you, too.

What’s Your Story?

Asking open-ended questions is an excellent way for someone to reveal different aspects of their life, and talk about whatever subjects they enjoy.

Research shows that we love talking about ourselves. Quoting an article from Psychology Today: “talking about oneself activates the same areas of the brain that light up when eating good food, taking drugs and even having sex. Simply put, self-disclosure is gratifying.”

So if you’re able to make someone feel good by talking about themselves, the probability of developing a relationship and establishing a meaningful connection is much higher.

Which Of Your Friends Or Family Do You Look Up To Most?

Seneca says, “you can tell the character of every man when you see how he gives and receives praise.” When you’re able to understand why someone gives respect, their core values in life quickly become evident.

Throughout my life, my mom has been at the epicenter of my respect. Having raised me & my little brother as a single parent, she’s always aimed to act in our best interest.

Earlier this year, she got diagnosed with Breast Cancer. Despite living in New Zealand at the time, I decided to fly back to the UK, so I could be with my family while she was having surgery & in recovery.

Take a moment to think about someone that you look up to with enormous amounts of respect. And whenever you find yourself in a conversation, ask the other person to do the same.

You’ll discover that it’s a genuinely humbling mental exercise.

What Book Had The Greatest Impact On Your Life?

I’ve discovered that you can tell a lot about someone by the type of books they read. After all, the kind of content we consume is what helps to shape our thoughts & identity.

Several months ago, my mental & physical health took a turn for the worse. I was unsure how to escape my constant negative way of thinking and quickly plunged into a spiral of depression. But while exploring the Calgary public library, I found a book titled “The Obstacle Is The Way” by Ryan Holiday.

Using examples from ancient philosophy, the lessons from that book helped me to change my perception of adversity, overcome my negative mindset, and live a much happier life.

Occasionally, you might find a book that completely turns your life around and enables you to live with a renewed sense of fulfillment. So asking people which book changed their life might help to improve yours, too.

What’s An Obstacle You’re Currently Afraid Of Facing?

Marcus Aurelius, the former Roman emperor, once said: “The impediment to action advances action. What stands in the way becomes the way.”

A great truth of life is that fear comes from uncertainty. However, you can also use fear as a motivator to grow as a person and overcome any obstacle that stands in your way.

For example, I used to be afraid of talking to strangers in public. But once I overcame my fear and began having conversations, my self-confidence massively increased as a result.

We don’t like to talk about the things which scare us. But whenever you have a conversation about fear, remember that embracing it can give you the courage to change the narrative in your head that’s preventing you from succeeding.

If You Could Restart Life, What Would You Do Differently?

Regret is something that we all experience, but often don’t want to face as it forces us to admit our mistakes.

However, I’ve found that when you reflect on your past, it provides an opportunity to reverse course and prevent the same errors from happening in the future. Lewis Carroll said it best:

“We only regret the chances we didn’t take, the relationships we were afraid to have, and the decisions we waited too long to make.”

When you become emotionally vulnerable about the past and tell your regrets to someone else, it immediately creates a feeling of trust between you both.

So if you want to have a thought-provoking conversation, talking about regret will help you to look back on the past and discuss ways to improve the future.

Creating meaningful relationships begins with the art of asking better questions, and listening with the intent to understand whatever the other person says during the conversation.

In the words of Epictetus: “We have two ears and one mouth so that we can listen twice as much as we speak.”

Remember: To generate meaningful relationships, all you need to do is listen.

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