25 Funny Questions to Ask Your Girlfriend

Sometimes a little bit of humor makes all the difference!

Getting to know each other, not just by spending time together, but also by asking questions is essential to any great relationship. What’s more, having fun is important! Goofing around can be just as needed as having time to tell each other your deepest secrets and explore what you need in a relationship. After all, having fun together is a big part of being happy together.

1. Can you make an impersonation of someone famous? 

If they can, naturally they will have to do it!

2. What’s the most ridiculous pick-up line someone has ever used on you or your friends?

Obviously if you guys are sixteen and haven’t started going to clubs and bars yet, this question might not be relevant. But if you are dating someone older and she’s the kind of person who likes to go out, she’s sure to have had some interesting (and hilarious!) come-ons from men.

3. What’s one movie that made you almost wet your pants as it was so scary? 

Let’s just pray it wasn’t a Disney movie…

4. What’s your favorite prank to play on people? If you aren’t a prankster – what’s the best prank you’ve ever seen/heard about? 

Pranks can lead to a lot of hilarity and trouble (if they go wrong).

5. What’s your favorite comedy?

Sharing fun moments from movies can be hilarious.

6. Who’s your favorite comedian? Tell me some of their jokes!

Might bring about a few laughs!

7. If you were to turn someone we both know into a caricature, what are the features and traits you’d bring forth in them? 

Everyone has sides that can be made fun of (in a nice light)!

8. What cartoon character has brought you the most laughs through the years? 

Hopefully they’re actually funny!

9. What political figure have you heard the funniest jokes about? 

If she can’t remember any good jokes about politicians, just Google jokes from the late night TV show hosts. Their sharp tongues have poked fun of both democrats and republicans.

10. What’s one thing you’ve done that was really embarrassing at the time, but that you now find funny? 

Most of us have ended up in the kind of situation you wish only happened on TV. The sit com situation of your life.

11. What’s the weirdest thing you’ve ever heard a person do? 

People do a lot of strange things. If she can’t think of something then google it as there are plenty of weird things happening out there.

12. What’s the craziest thing you’ve ever done? 

Always good to know… After all, you might be dating a maniac!

13. What’s a pet peeve of yours?

Some of our pet peeves are truly ridiculous and, actually, funny.

14. What’s the weirdest name you’ve ever heard someone give to a child? 

These days you might just be named Appleseed if you don’t watch out!

15. Tell me how NOT to impress a woman. What are the worst things a man can do to impress?

Listen carefully now…

16. Who’s the biggest drama queen you ever met?

Usually these come with a bunch of funny stories attached.

17. What’s a funny childhood memory of yours? 

Most of us have been through a couple of funny situations growing up.

18. Did you ever do something really naughty as a kid? 

Who didn’t?

19. What’s one thing you’ve done to impress a guy that completely failed?

We’ve all been there…

20. What are some EPIC FAIL moments of your life that are hilarious looking back?

That one time you slipped on a banana peel in front of your crush…

21. Who’s the funniest teacher you’ve ever had at school?

An impersonation might be the next step here…

22. Have you ever burst out laughing at a time when it was really inappropriate? 

Sometimes fear, nervousness and other such feelings make us laugh at just the wrong time.

23. Have you ever had a really weird dream?

Probably. Only question is if she can remember it? Might give you a nice insight to her psyche…or make you want to run for your life!

24. Who is so not funny it’s funny? 

Some people become hilarious as they are trying so hard not to be.

25. What’s one thing that always makes you laugh? 

Could be a memory, a cartoon, or a person!


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