10 interesting questions to ask on a first date

Dates, and especially first dates, can be pretty awkward and nerve-wracking. If you hate small talk, it can be hard to have a flowing conversation with someone you haven’t known for that long. You want to leave a good impression and ask the right questions.

Below are 10 interesting questions that will make your date a lot less tense.

What are you best known for among your friends?

This is a great way to understand your date’s friendship dynamics and whether or not you would get along with their circle of friends. Are they the clown of the group? The responsible one? The unreliable one? The one who’s always late to meetups?

What is your no.1 guilty pleasure?

This could be a TV show, a dessert or a weird habit. We all have guilty pleasures that we like to indulge in every now and then. Remember not to bash their guilty pleasure because this is something that brings them true joy outside of their day-to-day activities.

What’s the most embarrassing thing that’s happened to you?

Most of us aren’t comfortable sharing our embarrassing moments but it would be great to see if your date can laugh at themselves and that will help you know if they have a great sense of humour. This question also allows your date to be vulnerable with you in a humorous way.

What’s something you’ve tried and would never do again?

I’m pretty sure we’ve all tried something that we would never do again. Whether it was a new hairstyle, a foreign dish, going an entire day without caffeine or procrastinating an assignment until the very last minute and losing our mind rushing through it before sunrise.

What is something you’re proud of?

This is the kind of question that will make the person sitting across the table from you scratch their chin and look up in search of an answer that will impress you. Proud moments are relative, so for one person it could be the fact that they successfully quit smoking while for another it could be as grand as buying their first home before the age of 25. Don’t judge them if their proud moment is small compared to yours, simply congratulate them on their accomplishment.

What dating advice would you give your 18-year-old self?

Many of us made relationship mistakes in our young, naïve years. The answer you get will give you insight into how the person perceives themselves then and now, and if they’ve grown from those experiences.

What is the worst punishment you ever got growing up?

If you grew up in an African household, you’ll know that discipline was part and parcel of your childhood. Different parents and guardians discipline their children differently, and most of the stories are really funny. If the response you get sounds like child abuse and seemed to traumatize your date, be sure not to laugh at them.

Would you rather…?

This is a playful way to get an awkward conversation going. There are actually phone apps that let two players choose what they would rather do, say or eat. Your answers will have you both laughing and this will lighten up the overall mood.

If you could be the opposite sex for a day, what would you do?

There’s so much that we can learn from the opposite gender but actually being one for an entire day would be interesting. This is another funny question and the answers you get will probably have you in a fit of laughter.

What’s the worst date you’ve ever been on?

Hopefully, this date doesn’t turn out to be the worst date that they’ve ever been on. This question will also be less awkward if the date is actually going great.