22 Random Fun Questions to Ask Your Girlfriend


The science is in: Girls love funny guys. Few things turn them on faster than a good sense of humor.

Don’t consider yourself to be funny?  Don’t worry. All it really takes is a bit of light-hearted comedic banter to keep your conversations upbeat.

The following are some of the best fun and funny questions to ask your girlfriend.

1. What phrases have guys used to try and conquer you with?

This is a very fun question to ask your girlfriend, and her response will probably make you laugh out loud.

It will also show her that you have a sense of humor. Because, you know, girls love funny guys.

2. If you could jump into a pool full of something, what would it be?

Her answer can be anything — a pool of candy, money, stuffed Baby Yoda dolls, just you name it.

This seemingly silly question can tell you a lot about the kind of person she might be. Is she down-to-earth, serious and goal-oriented, materialistic, etc.?

3. If you had a superpower, what would it be?

How could there be a list of funny questions to ask your girlfriend without mention of superpowers. Who doesn’t wish they had superpowers?

The answer to this silly question can vary from person to person. Maybe your girlfriend wants the power to read minds so she could hear what YOU are thinking about her, in which case I pray for her.

Having access to a guy’s mind can traumatize a girl for life.

4. What is your destination for the trip of your dreams?

Many girls love to travel. If your girlfriend is one of them, brace yourself for an engaging conversation about the many wonderful and interesting places around the world.

Even if she isn’t a traveler at heart, there is likely one place she dreams of visiting. What is it?

In addition to helping you find out if your desires are similar, this question could make her think you want to travel with her somewhere, an idea girls tend to find tempting.

5. If you could live anywhere, where would it be?

Most people aspire to live somewhere they frequently visit, if at all. Maybe she has one or even several.

Is it a place brimming with activity or one that’s relaxed and downtempo? Is it some far-flung location that no one has ever heard off?

As you can see, this question can tell you something about her personality and spark an engaging conversation that branches off into other topics.

6. What are your secret skills? What skills do you want to learn?

Girls love to talk about themselves, and your girlfriend is almost certainly not an exception. Here is her opportunity to brag about herself.

If you’ve been together for a while and think you know her very well, her answers might surprise and even shock you.

Definitely one of the most peculiar questions to ask your girlfriend.

7. What is the most embarrassing thing that happened to you?

If there’s one thing as certain as death and taxes, it is that we will all make a complete and utter fool of yourself many, many times throughout the course of your life. I’m talking about those truly cringeworthy moments that still make you shake your head in disbelief.

Have her reveal the funniest incidents first if you don’t want to embarrass her, and then continue to more somber ones. I am sure the two of you will get a good laugh out of this question.

8. What things would you grab if your house was on fire?

We all have material objects that we cherish and appreciate. This fun question to ask your girlfriend can reveal a lot about her life priorities.

She could pick anything really. It could be fun, wacky, or something novel and practical.

Instead judging her, find out why she picked those particular items.

9. If you got stuck in the elevator and was forced to listen to only one song, which would it be?

Taste in music can say a lot about a person. Did you know that people who are high on empathy tend to prefer mellow music that evokes deep emotion, while those who are more systematic prefer intense, more hard-hitting music?

This funny question to ask your girlfriend is a more interesting way of finding out what she likes than simply asking what her favorite band or artist is.

10. Do you prefer texting me so we can spam each other with emojis or call so we can hear each other laugh?

Definitely one of the most random and silly questions to ask your girlfriend. She won’t see it coming.

Use it as an ace card. If your girlfriend takes pleasure in talking to you and having silly conversations, then you and my friend are one lucky guy.

11. Since people from Poland are called Poles, why are people from Holland not called Holes?

A completely silly and random question to ask your girlfriend, let alone anyone. But, sometimes, the silliest questions lead to the biggest laughs.

Try this one on her and see how it transforms the conversation.

12. Would you rather be trapped in a dark small box or at a Justin Bieber concert with no doors or windows?

Justin Bieber gets a lot of hate, and probably for good reasons. It may have to do with his music, his personality, the way he looks, or a combination of the three.

What could possibly make her want to choose a dark, claustrophobic box over this Canadian?

13. Have you ever been in a cat fight?

Every girl has been in at least one or two cat fights in her life, so your girlfriend is probably lying if she says she hasn’t.

It will be fun listening and laughing together as she spills the beans.

14. Ask the girl you like: Can you spell “supercalifragilisticexpialidocious” or say “Quizzical quiz; kiss me quick?”

Certainly one of the most, if not the most, random questions to ask your girlfriend. After wiping the “WTF?” reaction off her face and untangling her twisted tongue, she might punch you for pulling such a fast one.

Feel free to make up any silly, hard-to-spell word or string together any tongue-twisting phrase you want. You will both laugh, that’s for sure.

15. What is one funny thing that somebody has walked in on you doing?

This is a super funny question to ask your girlfriend for obvious reasons.

Perhaps it was when someone walked in when she was talking to herself in the mirror, or when she was busting some crazy dance moves. Heck, you might even have been involved in the incident!

Whatever it was, the two of you will certainly get a laugh out of it.

16. What’s the most funny prank you’ve ever pulled on someone?

All of us have pulled a prank or two on someone before, but some people were just born to prank.

Is your girlfriend a born prankster? Should you be on your guard for shenanigans?

This fun question should result in an upbeat conversation.

17. Why do girls usually push the door when it says pull?

It sounds like a silly question, but this strange behaviour is a mystery that even girls don’t understand.

I’m sure there is a scientific basis for it, but see what funny explanation she can come up with.

18. Me, a rabbit, and a panda: cuddle one, hug one, kiss one?

One of the cheekiest questions to ask your girlfriend, that’s for sure, and certainly one that will make her laugh.

It will be fun and interesting to see what she chooses. And judging by her options, you win no matter what.

19. If I offered to do something really funny for you, what would you ask me to do?

This one will put you in the limelight in a big way, so be prepared. You will be at the mercy of her imagination… a woman’s imagination.

She can literally ask you to do anything, from the mundane to the downright weird. Just don’t be surprised to find yourself walking around in public wearing lipstick, high heels, or both.

20. If you could be a man for just one day, what would you do?

Few questions to ask your girlfriend have the potential to be as fun as this one.

Every girl has wondered what it would be like to be a guy, so this is her opportunity to share what she thinks guys do.

Even if her answer ends up being wrong on so many levels, you will both find levity in poking fun at guys.

21. Don’t you think it’s a crime for you to be so beautiful? Don’t you think you need a handsome guy like me?

This is a shamelessly corny question to ask your girlfriend, and that is precisely why it will likely put a smile on her face.

Just don’t be too serious when asking it, OK? The last thing you want is for her to think you are vain.


22. What would you do if you could be invisible for one day?

Like any normal person, she could probably think of 100 different things she would do.

Would she play a prank on some she knows? Take a nap at work? Sneak into a men’s locker room?

You are bound to get some interesting answers, along with some good laughs.

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