10 Interesting Questions To Ask On A First Date

Photo by Viktoria Slowikowska

On a first date, we’re discovering as much as we can about the person sitting across from us, deciphering whether the connection has the potential to grow into something lasting and true, or if it will remain a one-off dinner date that never leads to a second date.

More often than not, the conversation dictates how we feel about our date — did it flow naturally, or did it feel stilted? Was it enjoyable, or was it draining? Did it make us want to know more, or was two hours more than enough?

But good conversation doesn’t just happen. It’s something we have to intentionally create through thoughtful, unique, and compelling questions that allow for more interesting topics than So, where did you grow up? Did you take Main Street here? Do you like pizza?

Still, we don’t want our questions to end up feeling more like a job interview, and less like a romantic outing. So here are 10 questions to ask on your next first date that will create meaningful conversation without being too serious.

01 | What do you love most about where you grew up?

So you can learn where they’re from while also discovering what about their hometown holds a special place in their heart.

02 | What are you reading right now?

You’d be surprised how much you can tell about a person based on which books they have on their nightstand.

03 | What’s another profession you could see yourself doing?

This will give you deeper insight into their personality, their skills, and their passions.

04 | What’s your Myers-Briggs personality type?

Need we say more? Knowing a person’s MBTI is key in understanding their motivations, inner workings, strengths, and weaknesses.

05 | Who do you talk to most in your life?

The person they talk to most is the one who will have the most influence in their life.

06 | What does your ideal Saturday look like?

The way someone chooses to spend their free time says quite a bit about what they value most.

07 | Which fictional character do you identify with?

A lighthearted question that will offer you deeper insight into their personality than you might think.

08 | Do you have any hidden talents?

He’ll love the opportunity to wow you with his hidden talent, and you’ll learn another intriguing tidbit about him.

09 | What’s something interesting you learned recently?

Maybe he’ll come back with something silly, or maybe he’ll think of something genuinely fascinating. Either way, a new pathway of conversation will be forged.

10 | Who would play you in your biopic?

Bonus question: What would be the themes explored in your biopic? This will no doubt inspire a fun discussion.