9 Questions To Ask On A First Date

Photo by cottonbro

First dates often find us whirling with emotions; we hope we’ll make a good impression, that our hair will cooperate with us instead of falling flat, that we’ll be able to think of enough witty things to say that we won’t bore him, that there will be a second date. 

We put a lot of the pressure for a good first date on ourselves, focusing so closely on “performing” well that we entirely forget something important: we’re not the only person being evaluated; as exciting and nerve-wracking as first dates can be, it’s crucial for us to remember that the first date isn’t only for us to make a good first impression, but to assess whether or not our date is someone we like and desire to see again.

So how can we make sure we’re getting the right read on our date? By asking him a few key questions — it’s good to know where he grew up and what he majored in, but what other questions can we ask that will offer us a deeper insight into him, his life, his values, and whether or not he’s the right match for us — all while remaining first-date-appropriate?

01 | How do you spend your spare time?

While this doesn’t feel like a particularly deep question, knowing how he enjoys spending his “me” time, whether by playing video games, going on hikes, or catching up on reading, helps us understand what he values, and if our interests at all line up with his — after all, our spare time is spent on the things that make us uniquely us.

02 | What would your ideal life look like?

If he could snap his fingers and have everything he dreamed of and hoped for, what would his life look like, and how exactly would it differ from what it is right now? It’s important to get specific here — explore where he’d live, what he’d do for work, or what his days would look like. This can help us assess how well our ideals match up, if at all.

03 | What’s the last thing you read?

A reading man is one to search for — this tells us that he cares to invest in himself and his intelligence. Whether he prefers to read fiction, loves sifting through philosophy or theology, or likes to keep up-to-date by reading a host of news articles everyday, it’s helpful to know if he reads, and what he reads.

04 | What does a normal day look like for you?

We’re so used to simply living our lives that when we ask someone to outline their days, we’re bound to get an interesting, hopefully authentic, answer; but this question also helps us evaluate his lifestyle and whether it matches up with ours. Is he an early riser that has every moment of the day planned out, or does he like to take a low-pressure approach, taking things as they come? How does his answer fit into what we’re looking for?

05 | What’s the last show you binged?

The shows we consume say something about us, and the ones we binge, even more — our binged shows connect to something in us that all the others didn’t. Not only is discussing TV shows a fun first date topic, but swapping our binged shows helps us gain more insight on what sorts of stories, humor, and topics most affect him.

06 | Are you close with your parents/family?

Talking about family is a bit more personal, and not everyone will be open to discussing their family right away, but our family also has such a huge impact on us that it’s worth bringing up — so finding out whatever we can about his family and their dynamic is beneficial to us in putting together an accurate assessment; if he seems open to it, ask him if he has a sibling he’s always been closest with, or if he got along with his parents growing up.

07 | What’s the best gift you’ve ever received?

The gifts we receive say quite a bit about us; the one we consider the greatest we’ve ever received says mountains more. Get a few questions out of this — ask him when he was gifted with it, who gave it to him, and why it meant something so special to him that he’d mention it.

08 | Do you have a hidden talent?

Everyone loves to feel talented, to have someone in awe of their abilities, even if they’re “silly”. If we’re looking to lighten things up a bit, there’s no better topic than hidden talents. It’s of course entertaining, but also incredibly connective and could help break down any barriers as we ask for an illustration of their talent, if possible.

09 | What is your closest friend like?

We’ve all heard it said that we’re a combination of the five people closest to us, so best friends are important to take a look at. Ask him to describe his closest friend in order to grasp what he values in his close relationships, who he’s being influenced by, and what kind of person he feels he connects with.