The questions game two people talking

The Questions Game

The questions game is a brilliant get-to-know-you type date and is very simple. It could be over lunch or in the park, or maybe at night on your way to a movie. Or even over the phone, if you aren’t able to get together for a date that week.

The questions game is easy: each of you takes turns asking each other creative questions in order to get to know them better. I’ve done this on first dates a couple of times, and it works pretty well. Especially if you are having trouble thinking of something to ask or say.

You can ask questions like, “What was your favorite cartoon growing up?” or “If you were going to be stranded on an island, what three things would you have with you?” That one is my favorite question to ask; it’s interesting what weird things people say they’ll bring.

Other types of questions could be “this or that” questions. For example, “Pancakes or waffles?” Get a little more creative and ask things like, “Cleaning toilets or organizing a sock drawer?” The key is to make sure a new question is asked each time, so if you like their question you can ask them the same one back, but then you still need to ask a new question after.    

What you need for the questions game date:

Man and woman asking questions

You don’t need anything. This is absolutely free. You could pick your date up and just go for a nice walk around a park or neighborhood and ask the questions. It’s that simple.

This date pairs well with other creative date ideas. It really isn’t a specific date idea in and of itself, but something to help you get to know your date a little better.   

My experience with this date: 

I’ve done the questions games several times, and probably the best time I had was years ago during Christmas vacation while in college.

I heard there was a group of people meeting up for an activity, so being the enthusiast that I am, I decided to attend.

I saw a rather attractive girl with a friend of mine, so I went and introduced myself to her. Her name was Jenny and she happened to be that friend’s new roommate.  Nice, lucky me. We seemed to hit it off pretty well during the five minutes of waiting around for the group to show up. There was casual banter that wasn’t forced but flowed. No awkward pauses, just good conversation.

Man and woman talking

She was into me from the start

She was focused on me while we were talking, not gazing around the room looking for who else might be there. That was a good sign. I in turn did the same, I was focused on her. My eyes and ears didn’t wonder.

The night’s activity was board games and twister. Being fond of board games I was excited to see how the night’s activities would unfold.

I decided to play twister and Jenny thankfully decided to join in. Being the incredibly inflexible person that I am, I lost every time. There were a couple of important things I learned that night, however: don’t wear jeans while playing twister, and that Jenny liked to play video games.

Girl playing xbox

At the end of the night, I gave her a ride home, since she lived in the same condominium complex as me, and invited her over to test her XBOX skills. I mean she did say she liked video games.

We didn’t play very long, but she wasn’t kidding when she said she liked video games; she could definitely hold her own at Halo.

Afterward, I suggested the questions game, and we talked into the early morning. She was digging me. We actually dated after that for a little while, but then for some reason, it didn’t feel right.

I was totally attracted to her, we had a lot in common, but the deep connection was not there. Surface connection, yes, but not the type I was looking for, and she felt the same way in the end. So ultimately it wound up working out for the best.

But the questions game was key and kept us both occupied in getting to know each other during that first impromptu video game and conversation date at my place.

Man and woman speaking to each other.
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The Questions Game Video

Now watch my video explanation about this fun creative date idea.

You can buy a copy of the book 101 Creative Dates: ideas, tips, and personal experiences from the life of a hopeless romantic here or visit the shop.

Here are some other date ideas that you might be interested in:

Play Board Games

Visit Downtown


Pedal Boat Ride

Go to a Rodeo