50 Deep Questions To Ask Your Girlfriend To Get To Know Her Better

When it comes to the science behind seeking out partners, men are generally moved by what they see as they are more visual than women, who on the other hand are easily swayed by what they hear. This is one of the many reasons why you could find that a beautiful-looking woman who would usually want a partner that meets specific societal criteria would fall head over heels for a man of lower standards just because of his way with words.

But after a man would have gotten to say all the sweetest things in the world to be with the woman he desires, he might still not be sure if he would want to spend the rest of his life with her. To come to this conclusion, he would need to change things up by asking his girlfriend a few deep questions. This will tell him whether or not they are compatible and have a future with each other. These questions should be able to pick her brains to understand her better, know what she wants from the relationship, and ultimately decide if the relationship will be heading anywhere.

How To Go About Asking Your Girlfriend Deep Questions

When asking your girlfriend deep questions that will inevitably decide your future with her, there is an inherent need to be strategic about it. It will be very unwise to ask questions that will upset or make her feel uncomfortable. This means you will have to be thoughtful about it all by deciding on what type of questions to ask and the best moments when to ask them.

If you have trouble coming up with any good questions to ask, worry not because we have compiled a list of 50 deep questions you can ask your girlfriend. We have further gone ahead to provide guides to a few of these questions, discussing what the question aims to achieve and why you should ask them. Enjoy!

General Personality Questions To Ask Your Partner

1. What are the things you fear the most in the world?

A whole lot more about a person can be uncovered by finding out what exactly it is that they fear; failure, poverty, old age, or losing a loved one.

2. What are the few things in the world that you would be willing to sacrifice your life for?

There are more than a few people in the world who are not willing to sacrifice their life for anything. However, there are a few others who would rather die than see a loved one do so. It is best to know what type of person you are dealing with when it comes to making scarifies and so this question will definitely set things straight.

3. What and what do you look out for to know that you are in a healthy relationship?

A fancy way of asking your girlfriend about her expectations of you and herself in the relationship. The presence of mutual respect, trust, honesty, and excellent communication.

4. What do you think the role of a woman in a relationship should be?

The role of women in relationships and marriage is a hot topic of discussion today. Different people have different views that are either shaped by history, culture, or feminism. Being on the same page about something like this will reduce the number of squabbles you will have.

5. What lies do you most often tell yourself?

People do not generally mean to lie to themselves. Some do not even realize that they are doing so. However, things like procrastination are one of the ways through which we do so.

6. If you could pick one, would you rather have infinite money or love?

A fancy way of asking her if money can buy her love.

7. Of all the movie and book characters you have come across, which ones do you feel most similar to?

You can tell a lot about a person by finding out what fictional character they feel like they share some similarities with.

8. If you could marry any celebrity of your choice in the world, who would you pick and why?

This is a great follow-up question to the previous one.

9. What’s a good relationship tip that sounds like a bad tip, or a bad relationship tip that sounds like a good one?

Girls usually give each other advice about relationships, and so it is most likely that an adult female would have heard almost every good and bad advice out there. Listening to what she regards as good and bad advice is a very good pointer in knowing your compatibility.

10. What’s the most romantic thing you’ve heard about someone doing for someone else?

Is she superficial or would she cherish the effort more?

Deep questions

11. What’s your most bizarre or weirdest deal breaker?

Some ladies are unable to handle their man being close friends with, or even working with, a member of the opposite sex. There are many other bizarre deal-breakers that make this question a must-ask.

12. Do you prefer staying at home or going out?

Many relationships and marriages have come to a screeching halt because one partner wants to, or always goes out, while the other prefers to stay home. The earlier this is discussed, the better for the relationship.

13. Which would you rather have: a short but exciting life filled with numerous adventures or a very long but boring life?

This question can lead to a whole other discussion about beliefs and the afterlife among many other things.

14. Would our relationship be threatened if I am suddenly able to hear your internal monologue, starting from the time I met you?

Your girlfriend will have to be sincere with her answer here because, without it, the purpose for asking the question will be missed. When truthful, a little bit more can be understood about her grievances towards you.

15. What would you do if you were suddenly tasked with improving the lives of the citizens of your country?

Remember, there is no right or wrong answer to most of these questions. The aim is to further understand how your girlfriend approaches things and how her approach might differ from yours.

16. What are some of the things that you would say you are either very good at or very bad at?

From the horse’s mouth, you get to hear about her strengths and weaknesses.

17. What are those things that you can’t wait to get off your chest about me?

You would have to tread carefully here because while you may want to hear everything that she has been bottling up, your feelings could get hurt with all she would have to say.

18. What do you dislike the most about our relationship that you would want to change?

A great follow-up question to the previous one as you still get to understand all her points of view and things she has not been willing to previously talk about.

19. Are you looking forward to becoming a parent?

For some reason, people generally assume that everybody in the world wants to have kids. This is not always the case and asking your girlfriend this question before walking down the aisle will save both of you a lot of grief.

20. Do you see us being together in our old age?

There is no better question than this to ask a girlfriend that you intend to spend the rest of your life with.

Sex-Related Questions To Ask Your Girlfriend

Deep questions

21. What is the one sexual thing you have done but will never do again?

22. What is your idea of a perfect Saturday night?

23. How often do you like having sex?

24. What is the best time of the day to have sex?

25. Outside the men you have officially dated, how many sexual partners have you had?

26. What are the craziest things you have ever done sexually with someone else?

27. Have you ever had unprotected sex?

28. Do you prefer your partner to be talkative or quiet while having sex?

29. Name three things that you have been afraid to ask but would like a man to do to you in the bedroom?

30. Where is the weirdest place that you have ever had sex?

Questions About Her Past

31. When was your first kiss and how did you lose your virginity?

32. What memory about an ex have you found hard to forget?

33. Who is the first man you ever had a crush on and did you ever get to let this person know how you felt about them?

34. How long did your most serious relationship last and why did it end?

35. Have you ever cheated on any of your exes and why did you do it?

36. What is the one thing that you did in a previous relationship that you would not want to ever repeat?

37. Has any other man ever asked for your hand in marriage?

38. Have you ever lived/cohabited with another man?

39. Even if you were in the process of breaking up with one boyfriend before dating another one, have you ever caught yourself dating two men at the same time?

40. Have you ever cried for a man and what were the circumstances that led to you doing so?

Questions About The Future

41. Do you think this relationship would have evolved into a loving marriage in the next five years?

42. What is the most annoying thing that a man you have married can do to you?

43. If you find out that I am unable to get you pregnant, would you leave or stay with me?

44. What are your thoughts on relatives living with us?

45. What particular thing about getting old do you look forward to the most?

Deep Questions About Finances To Ask Your Girlfriend

Deep questions

46. Either in a marriage or a relationship, should the man always be the one to pay the bills? Should the woman handle it sometimes or the best that can be done is for it to be split?

47. What household appliance typically found in a bachelor’s home do you think is a waste of money?

48. What are your financial priorities and goals?

49. How good are you with budgeting money?

50. If you could trade 1 year of your life for $30,000, how many years would you trade-in?


As mentioned earlier, the goal of asking your girlfriend deep questions is not for her to fail or pass them. Instead, it is for both of you to get things straight and understand the other person’s frame of mind. It would be best if you objectively listened to her answers and not pass judgment. If you find that you both disagree on a particular question, it does not mean that the relationship should end. The purpose of it all is for the questions to help you and she decide whether or not the relationship is the one worthy of going the mile.

It is also essential to have in mind that many of the questions that appear on this list are serious. Therefore, such questions should be asked at the appropriate times for the respondent to have the time to reflect and give a reasonable answer.

Joanne Lawrence
Joanne Lawrencehttps://www.skinnyscoop.com/
Joanne Lawrence is an experienced journalist and lifestyle blogger based in London, United Kingdom


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