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40 Open-Ended, Serious Questions to Ask a Girl & Get Her to Open Up

If you want to get to know her really well, then you should use these 40 open-ended questions to ask a girl. You’ll have fun and go deep at the same time.

sensitive questions

Deciding which role to fulfill is a real tough call for the modern guy in the dating arena. And that’s why you need to know some open-ended questions to ask a girl.

On the one hand, we’re told that all women love the alpha male, the bad boy, and the serial womanizer, yet when we act that way, we’re given a slap and told to shove off. On the other hand, magazines like to tell us that we have to be open to a softer, more considerate, more feminine approach, only to be told to “man up” and laughed off in disgrace.

Well, if you want to attract the woman who is right for you, then the answer is simple: BE TRUE TO YOURSELF. Acting a part is just going to deceive, in addition to mismatching you both.

40 Serious, open-ended questions to ask a girl

It’s important to have a variety of serious, open-ended questions to ask a girl. So, the following list is intended for men who are naturally more sensitive, and will help them open up to the current object of their affections. These questions are designed to open and reveal the soul.

1. What are the top five things on your bucket list?

A great question not only to try and work out the inner self of your partner, but also a chance to maybe try and facilitate her dreams. After all, what could show your sensitive side better than that?

2. What are you most afraid of?

Fear is a powerful emotion, and by asking this question, you have the opportunity to sympathize and empathize with her, as well as help her through her fears.

3. Are you an affectionate person?

Asking this question shows that you are keen to respond to her needs. It also gives you a chance to show that you are a lover of affection—if that is, indeed, the case. [Read: How to recognize the reals signs of affection to know someone cares]

4. If there’s anything you could have done differently, what would it be?

Regret is one of the most negative emotions, and by asking her this, you may be airing something she didn’t really want to… but it gives you a chance to talk her through it and show what an emotionally supportive rock you are. Support is an attractive, unusual trait in a male.

5. What’s your favorite…?

Food, place to go on holiday, perfume… etc. It’s an off the cuff kind of question, but whereas most guys would forget the answer in a heartbeat, you’ll be storing it up to surprise her on her next birthday, or other gift-giving occasion. [Read: 20 funny questions to ask a girl and leave her ROFL]

6. What’s your most special memory?

This question shows that you embrace all of who she is, even her past before you met her, and that you want to share her precious moments. This shows true emotional strength and a real sensitive side.

7. What’s your greatest passion?

Listening is a skill that most men don’t have. By asking her about her passion, even the most tight-lipped lady is likely to speak at length, giving you the opportunity to show just how strong your listening skills are.

8. What advice would you give your younger self?

 This question gives you rare insight into her personality, as well as showing your ability to assess and discuss deeply emotional subjects.

9. What would you do if you won the lottery?

Her answer is important, or course, but so is your response—especially if you’re the sort who would contribute it all to charity, rather than buy a tropical island! [Read: 50 relationship questions to test your compatibility instantly]

10. If I ever did anything to hurt you, you would tell me, wouldn’t you?

Women do not expect this level of sensitivity and emotional openness from a guy and they’ll find it hugely refreshing.

11. What are you most proud of?

Similar to number 7, this gives her a chance to express herself, and for someone else to take notice… a winner in the sensitivity stakes.

12. Do you need some space?

For the more in-depth and, perhaps, intense relationship, expressing this level of understanding and flexibility is likely to make you a saint in her eyes. And it could well save the whole thing.

13. Where do you see yourself in 5 years?

This is a great open-ended question to ask a girl. The reason is because it shows a true willingness to listen to and empathize with her aims and ambitions, but also subtly hints at the fact that you want to be part of her future. She’s bound to love that. [Read: How to balance your career, social life, and dating life]

14. Would you tell me if you were ever attracted to someone else?

Again, emotional honesty is a rare trait in a guy, and expressing this honesty without ire or accusation shows true strength of character and a very real sensitive side.

15. If you could change one thing about yourself, what would it be?

Find this out and then tell her, in so many ways, why you couldn’t possibly agree with her. [Read: How to charm a girl and flatter her into liking you]

16. Can you tell me if I’m doing it how you like it?

We’re getting a bit physical now, but sex is an important part of a relationship. Showing that you are sensitive to her needs is highly likely to increase your appeal.

17. What did you want to do when you were a kid?

You want to know everything about her—past, present, and future. That’s what this question tells her: her every moment matters to you.

18. How many people have you ever truly loved?

Discussing love can be very difficult—even for some women, but it is still a great open-ended question to ask a girl. For a guy to come out with this question, and to honestly reply with his own answer, shows a sensitive side that few can boast of. [Read: 20 Loving and romantic touches in a relationship to make you feel closer]

19. Do you want to try something new?

Whether you’re talking about the places you eat, the usual places you go on holiday, or sexual positions, this question shows that you are responsive and sensitive to her needs.

20. If you could change anything about me, what would it be?

What could better expose your sensitive side than an obvious willingness to change in order to remain in the life of the one you love?

21. On a scale of 1-10, how important is trust in a relationship to you?

This question can start a conversation about trust in general and what it means to her. Then you should tell her what it means to you and how much you value it.

22. What do you think is the greatest invention of all time?

This question will get her thinking outside the box a little. She needs to think about her life and see what she couldn’t live without. [Read: 35 Warm, feel-good questions to ask a girl to get to know her better]

23. Do you believe in telepathy? Why or why not?

This is a deep question that will get you to see how much she thinks about some paranormal things.

24. Is there a book that you have read that has influenced you the most? Why did it have an impact on you?

You really want to dig deep here and get her to explain why it had such an impact on her. How did it change her as a person – or did it?

25. What’s the most life-changing experience you have ever had?

This is a important serious, open-ended question to ask a girl. We all have pivotal moments in our lives. But sometimes people don’t talk about them, so now is your chance.

26. Is there a deal-breaker for you in a relationship – or more than one? What are they?

Hopefully she’s done some introspection through the years and come up with her deal-breakers. Once you know them, be mindful of not doing any of them! [Read: Dating checklist – how to make one and why it can benefit your life]

27. Are you a night or a morning person?

This might seem like a mundane question, but it really is a key to how well a relationship works. If one person is an early bird and the other one is a night owl, it has the potential to cause problems.

28. What’s the most important lesson your parents taught you?

This will give you a chance to see how close she was to her parents. Were they the kind to teach her deep life lessons or not?

29. What part of your body do you find the most attractive?

Girls probably aren’t very comfortable talking about their body. And depending on how close you are, you need to be careful with this one. But it is an opportunity to compliment her in a classy, tasteful way.

30. What would you do if someone cheated on you in a relationship?

She may not want to talk about if she has ever been cheating on the past, so you can start a conversation about what she would do in the future. [Read: How to rebuild trust after cheating – 11 things an ex-cheater MUST do]

31. Do you think there will come a day when humans are replaced with robots or AI?

If she says yes, then ask her if she is worried about it. Does she think the robots will be friendly or hostile towards humans?

32. Do you keep a journal?

When she answers, ask her about what kinds of things she writes about. You don’t have to ask for specifics, unless he wants to share.

33. What is your idea of a perfect date?

Listen carefully to this one. Whether you have never taken her out on a date or if you have been on many, you can make her dreams come true with this one.

34. If you could only choose three things that would make you happy for the rest of your life, what would they be and why?

This question will reveal what her values are and what things she treasures. [Read: How to be happy in life – 12 hacks to find real happiness instantly]

35. Which of the following is the most important to you? Career, family, or love life?

When you ask her this, see if what she says aligns with what you value. For example, if you want six kids, and she says career is more important that family, then you might not be a good match. That’s why this is an important open-ended question to ask a girl.

36. Do you believe in ghosts?

This is another fun supernatural/paranormal question. You can also follow up with asking her if she would stay the night in a haunted house if she had the chance. [Read: 25 Deep questions to ask a girl to see if you are compatible]

37. What is your favorite movie of all time and why?

Everyone has their favorite movies. If she has a difficult time choosing, then ask her to pick her top three.

38. Do you consider yourself more of a rule-follower or a rule-breaker?

This is an interesting question because you can tell how much she respects authority. Hopefully the two of you align on this one.

39. If you could have one superpower, what would it be and why?

If she has a difficult time answering, then you can give her some options such as: flying, reading minds, superhuman strength, living for 1,000 years – or choose your own.

40. What three adjectives would you use to describe yourself?

This will give you some insight into how she feels about herself. Also ask her if she thinks her friends and family would describe her the same way.

Final thoughts

These are some fun but serious questions to ask a girl. Whether you are trying to get to know her better or if you’ve been together for a while, you can still have a great time having some deep conversations with her about all of this

[Read: 50 really cute things to say to your girl that’ll make her love you more]

If you have a sensitive side that you want to expose to the woman of your dreams, then do so by asking these open-ended questions to ask a girl. By hiding it, you’ll only be hurting yourself—and you certainly won’t end up with the woman who’s right for you.

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David Cullen
David Cullen
David Cullen is frequently described as erudite, insightful and witty – but only by himself and only after several large glasses of Rioja....