During a first date, everybody wants to keep conversation flowing, but you also want it to go beyond small talk and into the realm of being able to really get a sense of the person you’re dating.

A date is basically an audition for the emotional capacities required for the success of a long-term relationship, a conversation to try to understand the other person. 
So how do you get to know your date without asking boring old questions?
Here are a few right questions to ask to help you to understand your date better.

If you could travel anywhere, right now, where would you go?

“If the answer is ‘nowhere’, you’ve got yourself a hermit. If the question elicits a string of destinations, you’ll discover what excites and appeals to them.

What’s something you want to learn/ get better at?

This question would enable you to understand if the person wants to develop or better themselves and how. It might show the person’s interests and aspirations – you can think about whether these align with yours and how you feel about it.

What’s something I wouldn’t guess about you?

This question has a bit of mischievousness and flirtation about it, and you’re giving your date the freedom to reveal as much, or as little, as they want.

What’s your favourite place on Earth?

This might help you get a glimpse of their lifestyle as it could indicate the places they want to go on holiday to or how they would like to live.


What’s your dream job?

You’ll find out what motivates and inspires them, while discovering values and character qualities that may (or may not) match yours.

What’s something you’re proud of?

This question can give insight into what is meaningful for them and might demonstrate their values. It’s a chance for you to see their self-awareness.