37 Questions To Ask Your Girlfriend or Date

In this article, we’ll deep dive into some great questions to ask your girlfriend and reflect on the power of active listening, and silence. 

I was on a first date last night with a hot French girl. She wasn’t the most chatty type, so I followed my 80/20 rule of conversation which states the man should do 80% of the talking (at least until you start banging.) 

In the attraction phase, it’s usually up to men to lead the conversation. Even if you have a chatty girl she might steer the conversation into boring, emotionally dry, or overly-logical topics. 

If you struggle with “what to say on dates” syndrome, I suggest you check out my free Conversation Genius course in the classroom area of my community. 

What Should You Ask Your Girlfriend? 

Creating great conversation with your girlfriend is important, because if you can’t do this you’ll probably be searching for “How to get my ex girlfriend back” rather than this article.

Personally, I get very bored with surface-level conversation. “So what do you do? Oh, that’s cool.” 

Chatting about the weather, work, school, and our favourite types of food, while fine for getting to know someone, doesn’t really create the strong bonds that deeper, more intellectual, emotional, fun, or even spiritual conversation can lead to. 

When you ask better questions, it can increase attraction, and demonstrate masculine/feminine polarity.

That’s why I’m sharing this list of good questions to ask your girlfriend (or date) so that neither of you get bored of talking to each other. 

Some of these questions are straight forward and some are downright bizarre. But they’re all guaranteed to steer a boring, emotionally flat-lined conversation in a more favourable, fun direction. 

Questions to Ask Your Girlfriend (or Date)

Great questions to ask her can make a boring, flat-lined conversation fun. 

I’ve broken these questions into 4 categories: Thoughtful, Philosophical, Sexual and my favourite… Ridiculous. 

Thoughtful

1. What did you want to be when you were twelve years old?
2. What’s the best (and worst) book you’ve read lately and why?
3. What’s the best (and worst) movie you’ve watched lately and why?
4. What do you prefer, beach or mountains?
5. If you had one day to live, what would you do?
6. If you could have dinner with any three people, dead or alive, who would they be and why?
7. What’s the most adventurous thing you’ve ever done?
8. If you could change one thing about the world, what would it be?
9. Are you closer to your Mom or your Dad?
10. Have you ever been in a fight?
11. What’s your favourite genre of music?

Philosophical

12. What do you think happens when you die?
13. Do you believe in reincarnation?
14. Have you ever seen a ghost?
15. Have you ever seen a UFO?
16. Do you believe in God?
17. What do you think is the meaning or purpose of life?
18. Do you believe in love at first sight?

Sexual

19. What’s the craziest place you’ve had sex?
20. What’s your favourite position?
21. Do you have a naughty sex fantasy you haven’t told anyone about?
22. If you could cheat with one famous man, who would it be?
23. Would you rather date a guy with a giant dick but no sense of humour, or a tiny dick but he’s hilarious?

Ridiculous

24. What would you do if you were a man for a day?
25. If you could have any three superpowers, what would they be?
26. If you could time travel and be rich in that time, what period would you go?
27. If you were trapped in a well with a cute squirrel and starving would you eat it or keep it for company?
28. What’s the weirdest food you’ve ever eaten?
29. What’s your go-to karaoke song?
30. If you were a character in a movie, who would you be and why?
31. If you could be any animal for a day, which one would you choose?
32. What’s the silliest fear you have?
33. Would you rather fight one T Rex or 30 angry midgets?
34. What’s the most unusual talent you have?
35. What’s the funniest joke you know by heart?
36. What’s the most dangerous thing that’s ever happened to you?
37. Would you rather live in the world of Harry Potter, Lord of the Rings, or Twilight?

Hopefully, some of these questions will inspire you to get out of the boring small chat zone, and into something deeper, more meaningful, and fun. 

Going Deeper

When asking your girlfriend these questions, don’t just listen to her answer and then change the subject. 

Go deeper with your own answers, even if they’re ridiculous or hypothetical answers. 

You can also tease her for her answers. She would rather fight the midgets than the T-Rex? What is she? Insane? Her silliest fear is farting in an elevator? But don’t her farts smell like roses? 

Active Listening

Active listening is when you bring your full attention to the act of listening or being “present” for your girlfriend. 

This lets her feel that you have her full attention and helps you to understand and remember her answer. 

It’s simple, imagine a beam of light, like a Care Bear going back and forth from your chest to hers. This will give you more focus to be fully present with her when she’s answering her questions. 

The Power of Silence

Sometimes men feel the need to fill empty space when it’s unnecessary. Instead of needing to fill the space, it’s also okay to just sit in silence with her. 

You can even seed this by saying: “You know what I like about you? That I don’t feel the pressure to talk all the time, and we can just chill in silence.” 

She may also enjoy sitting quietly, or if she wants to talk, she can ask you questions. 

Conclusion

These questions don’t have to be just for your girlfriend. If you’re single, they’ll work great on a date or cold approach as well. 

Remember, not all questions need to be logical. Actually, it’s better if they aren’t. Show your date, girlfriend or wife that you have an imagination and she’ll have an awesome time hanging out with you. 

Also, I taught you about active listening and the power of silence. 

Have a great time with your woman.