10 Out of the Box Questions to Ask on the First Date

There’s a lot that goes into a first date. I get that, I respect it.

There’s a lot to consider and think about when you’re in the dating world, from what dating apps to use, to what to wear, and where to go. When you hop on Wandure though, the where to go and what to do are taken care of for you! What a treat, right? This leaves you with more time to think about the amazing conversations you can have with your date. 

If you’re bored of the same old tired date questions, here’s a list of 10 outside the box questions that you might not have thought to ask! 

The backs of a man and woman staring at a lake with lush trees in the distance.

1. Have you ever changed career paths or majors?

Talking about schooling or work comes pretty standard with the first date. This takes it one step further than just “what do you do for a living?” or “what are you going to school for?” This question gets your date to actually open up about where they were at one point in their life and where they aspire to be. 

Even if your date isn’t that far along in their studies or working career, or  has happily stayed on their current path, it’s a good opener to discuss what they do now and why they love it (or don’t love it)!   

2. Which family member are you the most similar to?

Asking about family life can be like opening a can of worms - you never know how it’s going to go! 

With this question, you get to know a little bit more about what your date is like and get some insight into a family member they relate to and love (or at least, that’s the goal!) 

If you’re like me and come from a dysfunctional family, it’s nice to get specific questions like this instead of being backed into a corner where you feel as if you have to spill the family tea or awkwardly decline an answer. Give your date the opportunity to open up as much or as little as they would like.

Two women, one blonde and one brunette on a beach together, laughing enveloped in a colourful blanket.

3. What was your favourite age or year growing up?

Like the above question, you’re giving your date a no-strings-attached look into their past. Most people love talking about themselves, and being able to retell a favourite childhood memory can be fun for the both of you when you have someone that’s genuinely interested in listening! 

Walking down memory lane can spark some beautiful conversations, whether they tell you about how much they loved being eight years old and fishing with their dad, or being fourteen and spending time with their friends at the lake.  Hopefully you’ll get some lovely insight as to  who they were and what they value. 

4. What book would you love to see made into a movie?

As a bookworm, I love this question! I could spend hours talking about the good, the bad, and the ugly that is books turned into movies. And if you dream of your favourite books coming to life on the big screen, you’ll love the conversation that this question seeks  to ignite! 

Even if your date doesn’t happen to be a bookworm, it can easily fall into a conversation about favourite movies and TV shows. And maybe it’ll even turn into a conversation where you plan your next date at the movie theatre! 

Woman leading man, holding hands, walking past a pile of wood.

5. What’s something you’ve always wanted to try?

Whether it’s a type of food, a DIY craft, or a triathlon, curious minds must know! 

It’s a question that makes you stop and think. Even I paused to think and dream about this one (it’s skateboarding, if you were wondering), and hopefully it’ll open up an opportunity for the two of you to plan something together. 

It’s also another opportunity to see where your date’s interests and priorities lie - and hopefully they mesh with yours!

6. What are you always game for?

Is your date always down for a hike that’ll get their heart pounding? Or would they never turn down a night to binge-watch The Office? This question is a great chance to see if you’d be down for similar things. 

Of course, having different things in common isn’t a bad thing. Maybe your date would jump at the chance to do something you could never see yourself doing or had never thought of, such as kayaking or karaoke. This question can even act to open up your own mind to activities you may have never considered before.

The tip of an orange kayak in a dark body of water between large mountains on either side.

7. Are most of your friends single, dating, or married?

I like this question because it gives you some insight to what their friend group is like. 

If your date is friends with a bunch of married or engaged folks, they probably have different values and priorities than a group of single friends. This isn’t to say that one is better than the other, but who your date surrounds themselves with is an important aspect of who they are. 

If your date has a gang of single pals, you’ll probably find that they spend more time together and go out more frequently. Whereas a bunch of dating or married friends will be preoccupied with their own relationships and maybe a bit more low-key. 

Again, neither are necessarily good or bad, it just depends on where your own priorities lie. It’s also a good opener to get a feel for how your date feels about single life versus dating life. 

8. What’s the last thing you Googled? 

I think this question can be such  fun. Aside from all the boring questions I’ve had to google for school assignments, my google search history is… interesting to say the least. 

It’s where we go to ask the silly, sometimes embarrassing questions we don’t want to ask our friends. Or where we turn when we have a super specific question that’s driving us crazy. 

As long as you or your date’s search history isn’t too scandalous or gross (unless you’re ready to dive into the spicy and weird aspects of each other), this could be so fun to discuss! 

Get them to tell you why they googled the lifespan of an octopus or the best questions to ask on a first date (hello, we see you!) But be ready to tell them yours in return!

Woman in navy bathing suit, photo taken underwate, octopus on her stomach.

9. Tell me your favourite joke.

Humour is so attractive, isn’t it? Someone that’s funny and witty can just keep the conversation flowing.

While humour isn’t everyone's strong suit, we all love a good chuckle, right? Even the worst dad jokes can earn a giggle from people, so hopefully this question doesn’t put too much pressure on your date. 

I have such a fond memory from one of my first dates with my partner where he came up with this awful Scooby-Doo joke, but shockingly it made me laugh! We still chuckle about it today and I make him retell it to me when my spirits need a brighten. Maybe this could lead to your future inside joke, too! 

10. If you could give everyone just one piece of advice, what would it be? 

Yet another question to see where your date’s values lie! This type of question can reflect back on a time where your date could have needed it (story time, anyone?) or shed light on what they think is important in life. 

Either way, you’re bound to learn something about your date and hopefully be given some words of wisdom that you can keep in your back pocket for yourself! 

We’ve all been in a situation where conversation has plateaued. It’s cringeworthy when we think back on it, isn’t it? Hopefully these questions arm you with the spice you need to season your date perfectly! 

Happy dating and conversing, folks! 

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