9 Unexpected Date Questions You Have Never Thought Of

Date nights can feel boring when you ask the same old questions all the time. If you’ve already run through the standard go-tos - Where are you from? What do you do for a living? What do you do for fun? - or just want to put a little more creativity and shake things up, here are 9 unexpected questions that will give you a lot of insight about your date.

Asking these questions will help determine if this person has what you are looking for in a partner so you can decide if their world is one you want to know more about or become a part of.

1. What’s your favourite thing about your hometown?

This is a great topic to cover as it gets your date thinking about some of the best times in their lives and create positive vibes. So keep it simple by sharing specific highlights and encouraging your date to share theirs.

2. Which book(s) have you read multiple times?

This is different from the standard “favourite books” your date has got used to. Sharing favourite books opens the door for an interesting conversation and finding common ground between you.

3. What’s your go-to meal when you’re home alone?

Everyone has a simple solution to eating solo at home. Does your date live off cereal when no one’s around? Do they order a  takeout? Or maybe they have a signature gourmet meal they can’t wait to share with you on one of the date nights.

4. What toppings are needed to create the perfect burger?

You’ll discover how particular your date is about their food, how adventurous they are and if you share each other’s food preferences.

5. What is on your bucket list?

This question gives your date freedom to share her dreams and interests with you. This list could include travel plans, career goals, personal milestones, or adrenaline-junkie adventures.

6. If you could go back to school or learn a new skill, what would you want to learn?

Would they start their own business? Play the piano? Learn Spanish? This is another great way to learn about your date’s passions and aspirations.

7. What’s the most embarrassing event you’ve ever attended?

This is a fun way to learn about each other’s guilty pleasures.  Sharing moments that have made you laugh, cry and embarrassed you helps to increase closeness and connection.

8. If you had to drop a holiday from the calendar, which one would you choose?

Instead of asking about favourite holidays, get your date to ditch one. It’s a tougher question and makes them think of family traditions and how they celebrate holidays.

9. Who in your family are you closest too?

This is a simple way to learn about who they trust and whose opinions matter most when it comes to approving of the new girl/guy.