25 Random Questions to Ask Your Girlfriend

Sometimes the random questions are the best ones – the ones that make the conversation flow and the laughter ring out. They can also lead to some pretty deep discussions about life, love and dreams. It all depends on what randomly comes up in the conversation…

1. If you were a character in a movie, or a TV show, who would you be?

Haven’t we all fantasized about being Lois Lane, or Cat Woman? No? Just me then…

2. Who’s the worst boss/teacher you’ve ever had? 

There are often some funny stories attached to this!

3. Who’s the best boss/teacher you’ve ever had? 

It can be real inspiring to find out what your girlfriend admires in a boss/teacher. Usually great stories about what makes someone a good leader.

4. Have you ever made a complete fool of yourself?

Be prepared to laugh!

5. If you were a dog, what kind of dog would you be?

Are you dating a terrier or a German Shepherd? Maybe a Boxer?

6. What’s the most adventurous thing you’ve ever done? 

Sometimes when inspiration strikes people they end up buying a flight to the other side of the planet, other times they decide to go bungee jumping. There are other things that are just as adventurous in a completely different way though – such as confessing your love for someone.

7. What’s a pet peeve of yours?

Because don’t we all have them?!

8. Do you have any heroes or people whom you greatly look up to?

Will tell you a lot about what she thinks are great traits in people, what inspires her, etc.

9. Did your parents ever totally embarrass you? 

Most parents did at some stage. And looking back it’s often hilarious, even if it was no laughing matter at the time!

10. What are the kind of rules that are meant to be broken? 

This could be a fun discussion!

11. What’s the most ridiculous thing you’ve ever heard a politician say?

Probably quite a few things…

12. What’s one thing you’ve never told your mom/dad about? 

Chances are there are plenty of things she’s never told her parents about, but try to find out about the one she would never tell them about!

13. Thai of Chinese food? 

What’s her preference? From there you can move onto Italian v.s. French, etc.

14. Have you ever kissed a stranger? 

Because randomly, that’s what you do.

15. What’s the scariest movie you’ve ever seen? 

Maybe she doesn’t like scary movies, but then at least you will know before you take her on a date where you watch a horror movie…

16. Would you ever move countries? If so where to?

This question obviously only works if she hasn’t already moved countries. In that case ask her if she’d ever move to yet another country!

17. If you were given a billion dollars, what would you do with it? 

Play time! Imagine all the things you could do!

18. Who would you interview if you could interview anyone? 

Have them name one or a few people they admire, find really interesting, etc. Will likely reveal a lot about who they are too. After all, there’s a difference between Britney and Branson…

19. If we could be anywhere in the world doing anything right now, where would we be and what would we do? 

Oh this is kind of exciting, isn’t it? It might reveal a thing or two about her secret wishes and desires!

20. Do you have a dream you haven’t told anyone about?

Sometimes people avoid telling others about dreams that are really precious to them for fear of failure, embarrassment, etc. Maybe your girl has secret dreams you never knew of…

21. What’s the quirkiest thing about you?

We’re all a bit quirky, aren’t we?

22. When did you stop believing in Santa Claus? 

If we are going to go random, we might as well go really random…

23. What’s a movie you wish you had experienced the plot of?

Maybe she always secretly dreamt she’d be Cinderella, or have Sarah Jessica Parker’s lifestyle in Sex and the City. If she wish she was the lead in Kill Bill you might just start reconsidering dating her though…


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