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Questions To Ask To Deeply Connect With Your Date

Dating can be an emotional minefield, and when it comes to those crucial first few dates, the questions you ask can make a world of difference.

We’ve all been guilty of asking the super generic ones, like;

“What do you do for work?”, “Do you have any hobbies?”, and “What kind of music do you like?”

Today we are going to dive much deeper.

It’s time to get to know your date beyond the everyday dating conversations and find out if you’re truly compatible. 

Why are the questions you ask so important?

Glad you asked! This isn’t just me being esoteric, there is good science behind it. There’s a fascinating study by psychologist Arthur Aron (and others) which explores how mutual vulnerability can increase emotional connection. Here’s a quote from the findings: 

So, while we can understand in theory that vulnerability is key for connecting with others, it can be incredibly challenging in practice. This study has 36 specific questions, separated into 3 different sections, each more intimate than the last. (Click here if you’d like to read the full list).

Popular culture seems to have latched on to these exact 36 questions as being the code for emotional intimacy, which isn’t the case. The study actually discusses how the questions themselves aren’t as important as the acts of listening, sharing, and emotional disclosure. 

The feeling of closeness is what people love, not the specific questions themselves. In fact, they even say in the findings:

I believe the important message of this study is that repeatedly practicing vulnerability can encourage a genuine connection to blossom. But how do we apply this to the real world? 

How To Ask These Questions

Okay, so at this stage of reading, you may be wondering how you could just whip out a list of 36 questions to ask your date without looking… rather eccentric. Honestly, I think it’s kind of a fun first date idea, but then again, I’m pretty eccentric myself.

The key point to understand though is it doesn’t matter as much what specific questions you ask, as long as they are emotionally vulnerable. 

To help you get started, I’ve picked my favorite question from each of the three sets, and explained why they are useful questions to ask on a date. 

1- What Would Constitute A “Perfect” Day For You?

I love this question because it gives you such valuable insight into your date’s vision for their life. Listening to how they describe their ideal day can show you what their goals are, what they value, and where they would like to go in life. See what perfection looks like to them. 

I would suggest adding a follow-up question of “how different is that from your current day-to-day life”. Adding in this question reveals how different (or similar) their future goals are with their present reality. 

Plus, if their perfect day sounds like your actual nightmare, well you’ve just saved both of you a lot of valuable time. 

2- Is There Something That You’ve Dreamed Of Doing For A Long Time? Why Haven’t You Done It?

This question gives you a glimpse into their desires, as well as valuable information about the choices they make in life. While the first question is certainly interesting, personally, I think the latter question is the most insightful.

Plus, the reasons why someone might hold themselves back can certainly affect you if you continue on to have a relationship with them. Do they allow themselves to indulge in pleasure? Why or why not?

Consider the similarities for each of your answers. It’s an interesting opportunity to asses whether you think you’ll be a match to encourage each other to pursue your dreams, or end up at stalemates. 

3- What, If Anything, Is Too Serious To Be Joked About?

Humour is a fantastic way to connect, as well as something that’s pretty important when determining compatibility. This question gives you a little peek into their sense of humor. If you have a really different sense of humor to your partner, that may become quite challenging down the line. 

The other reason I love this question, is that it also provides valuable insight into the darker aspects of the psyche. Do they ascribe to the tradgedy+time=humor belief, or are some things just too much? With this intriguing date question, you’re sure to find out. 

The Perfect Question 

This one was a bit of a bait and switch… because there is no one perfect question! A perfect question is one that comes from your heart, feels vulnerable, and helps you get to know your date on a deeper level. 

So switch up the classic “where are you from?” questions and start diving a little deeper. You might just be surprised at what you find…

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