9 Great Questions To Ask Him On A First Date

First impressions really count.

So you show up to a first date ready to impress…and learn about him too.

If you’re like me, you want to sound intelligent and ask questions that will provide insight into what kind of person he is.

We’re trained through life to ask:

How are you?

What do you do for a living?

Do you have kids?

But those routine questions might not really tell us if we’re a good match. And while it’s good to know what they do for work, you probably knew that from his dating profile.

The other consideration is, it’s not always nice to put people on the spot with a really far-out question.

Some people come to dates with questions that are kinda fun and whacky, but sometimes they can be almost impossible to answer.

I mean those questions like, “If you could eat only one thing for the rest of your life, what would it be?”

They seem too silly.

But asking questions is a great way to make him feel like you’re an interesting person—funny how that works.

And questions keep the date moving along.

You want meaningful questions, but you don’t want to put him in the hot seat either.

So what kinds of questions will actually help you learn about him?

  1. How did your day go? What did you do today?

This is a good ice breaker if you haven’t been talking to him throughout the door.

And if you know what he did, but not how it went or many details, you can ask a more specific question.

This beats asking, “How are you?” or “How was your day?” 

  1. So do you think it’s fun meeting someone new like this? Or does it make you nervous?

Asking this can put him at ease because you can both admit to being nervous.

Or maybe you’ll find out he’s a real people-person and loves meeting interesting people.

I’m like that. I get a real rush from talking to someone and asking about their job and life. Most people have a story, and it can be inspiring and energizing to meet fun people. 

  1. Are you a music person? Movies? Sports fan?

This one you might want to customize and try to pick two likely things.

This kind of question can get men talking about their interest, and giving them options means it’s less likely he’ll give you a simple “no”.

If he does say no to your 2 or 3 things, ask him what he is into.

You can also say, “You mentioned you really love classical music, is that the only kind?”

  1. Do you read? (Cycle, hike, scuba dive, etc)

(Or something that YOU like to do or are interested in.)

It helps to know a little about him before coming to the date, but you can always start with your interests and ask him if he likes it too.

  1. Do you get free time in the evenings or weekends to do fun things?

This is a way of asking him what he likes to do, and also if he actually gets time to do those things.

You might also learn a bit about his schedule and how busy he is, or if it matches up with yours at all.

It’s good to know if he’ll have time to spend with you!

But don’t try for specifics. Just ask generally if he gets time to enjoy his hobbies. Otherwise he might feel pressured too soon.

  1. Is your career what you expected it to be like?

This is a different way of asking about his job, and gives him a direction to go in.

Maybe he loves it, or maybe he’s thinking about switching fields.

This question might let you see how optimistic he is, or if he’s someone who complains all the time.

  1. Do you get to see your parents or other family often?

This can replace the usual question of, “Do you have family here?”

Because that doesn’t tell you how involved they are in his life.

This one tells you if he values family, and it can also tell you if he goes home to have dinner at his mom’s every night. (You can decide if that’s good or bad.)

This question is open enough that he can tell you about his parents, or maybe a brother he sees a lot, or friends he considers family.

  1. Are there any hobbies or other things you want to try? Or something like a bucket list?

This tells you if he plans for the future and has dreams.

Dreams and goals are just fun to talk about too, and you can explore quite a bit: where you want to travel, things you would never want to do, hobbies you want to try but are nervous about, and so on.

It’s good to have some questions that are fun and still revealing.

  1. Say you got to plan a fun outing for a date, what would you want to do?

With this one, you can explain it a bit: would you want to go for a hike and picnic, hot air balloon ride, to a rodeo, or out dancing?

It can be fun to see what the two of you come up with for fun outing ideas.

It can also show you how excited he is to think about doing something else with you, and even if he likes to get out and do things or if he prefers to grab dinner instead.

These questions are designed to encourage conversation and help both of you get to know each other, all while making the date more interesting and fun.

It’s always good if you can see if you match up on some things too!

And hopefully you can see how to design questions for better answers and better dates—it’s great if you can go into it without expectations and enjoy talking to someone.

Good luck out there!

Find out what she did with that text! (WOW!)

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