Fun Questions To Ask On A Date


Image © Men’s Fitness

Here are some fun ways to learn more about your date that I’ve picked up from friends over the years. Of course, they are only one piece of the puzzle, but they’ve always led to interesting conversations.

– Nikita


Starter Questions

1. What is your favorite color and 3 words or phrases why you like this color?

2. What is your favorite animal and 3 words that describe why you like this animal?

3. What is your favorite body of water and 3 words that describe why you like this?

Starter Answer Meanings

1. Color: The 3 words represent how this person sees themselves.

2. Animal: The words they chose represent the qualities they are looking for in a romantic partner.

3. Body of water: Sometimes people get confused by this question. It’s supposed to be the first thing that comes to mind, maybe it’s the ocean, a lake, river, stream, waterfall, or even a bath. The body of water they chose is supposed to represent their sex life, or what they’d like it to be.


The Cube 

(You’re going to be narrating this story. Tell the other person they can close their eyes if they want. You will be asking a few questions throughout the story – do not define the meanings til the end of the story – just keep track of their answers in your head.)

Imagine yourself in an infinite white cube that is so big you cannot see any of the sides or corners. Now imagine a smaller cube inside that infinite cube with you. What size is the smaller cube? Is the smaller cube floating or is it on the ground? Now visualize a ladder inside the infinite cube with you. What does your ladder look like? What kind of material is it made of? Do you want to climb it? Now visualize a horse inside the infinite cube with you. Describe the horse and what it is doing? Now visualize some flowers inside the infinite cube with you. What kind of flower(s) do you see? How many are there? Now imagine a storm off in the distance. The storm is beginning to approach, how do you feel about that – what do you do?

The Cube Answer Meanings

– The infinite white cube is the person.

– The size is the smaller cube represents the size of their ego.

– If the smaller cube is floating it means they are more creative. If it’s on the ground it means they are more analytical.

– Ladder: Represents their ambition. Generally the taller the ladder, the more ambition they have. A short ladder doesn’t necessarily mean they have little ambition, it could just be that they set realistic goals for themselves and once they reach them, set new reachable goals. A top-out-of-sight ladder isn’t necessarily positive either, it could mean their goals are unreasonable or unreachable. I added the part about what kind of material it was, my best guess is that the material the ladder is made of represents the path or way in which they will achieve their goals.

– Horse: Represents a romantic partner (current or to-be).

– Flowers: Represent this person’s friends. Maybe they see a whole bunch of different kinds of flowers all over the place – it probably means they are pretty social and are friends with many different kinds of people around the world. Or maybe they have a few tulips in a vase, it probably means they have a few solid friends they are close with. The vase could mean a number of things, maybe like like to keep people at a bit of a distance, or “contain” people to one area of their life. You’re the interpreter here!

– Storm: Represent the problems in life, and more importantly how this person approaches them.



Ask them to imagine themselves holding a bouquet of 20 flowers in any combination of white and red roses. Supposedly the ratio of white to red roses represents how much they like to give vs. take in a relationship (white being selfless, red being selfish).


Roller Coaster

Ask them to picture themselves waiting in line to get on a roller coaster (if they don’t like roller coasters, ask them what rides they do like, and then ask the question again with that new ride). Where do they see themselves in line – how long til they get to ride the roller coaster? The amount of time til they get to the ride indicates how much foreplay they need.


The Spider’s Web

Ask them to imagine themselves as a spider. Now ask them to spin a web anywhere they want. Have them describe the web they built and where they built it. Now ask them to imagine an insect got caught in their web. Now ask them to approach the insect. Suddenly as they are approaching the insect escapes from the web! Ask them to describe the insect and how they feel when it escaped; it is supposed to represent the ‘one that got away’.