Never have I ever Play Now

We’ve put together a list with 100 questions for your girlfriend to deepen your relationship. Most of the questions cover a more serious topic. So if you’re just looking for some fun, casual questions, head over to this page: Fun questions to ask a girl.

Questions about the future

Looking for a long term relationship? These questions will help you get a rough idea of what direction your lives might be like if you continue dating.

1. Take a minute, close your eyes, and imagine what your perfect life would look like. Describe it in as much detail as possible.

This question and the one following it are great for finding out what she wants out of life and the life she would live if everything went perfectly. You can compare your girlfriend’s answer with your own goals for life and see if they match. So, if your perfect life is traveling around the world with nothing but a backpack and no cares, but her perfect life is building a business from the ground up, well, you two have some talking to do.

2. What would an average day in your perfect life look like? Do you have just one ideal life, or can you think of more than one?

Also, even though they tell you a lot, they are still great lighthearted questions that you can bring up whenever.

3. What do you think the role of a woman in a relationship should be? How about the role of a man?

This one is very important to ask so that you can go into the relationship on the same page as far as roles go. If you both have wildly different ideas about both of your roles, you’ll need to get that settled before you get too far into the relationship.

4. Should roles change when a couple gets married or moves in together?

These two questions to ask your girlfriend are great for seeing how both of your roles in the relationship might change in the future, or at least how she is expecting them to change.

You’ll want to check your expectations against hers and see how they match up. If you are looking for a more traditional relationship situation and she is more progressive, I guarantee you’ll both be on the road for some serious fights.

Questions about the past

The past has a lot of useful information for the present and the future. These questions will help you learn more about your girlfriend’s past relationships so you can learn more about your current relationship. Remember to pick the right time and the right place for serious talks about the past.

5. What was your most serious relationship? How long did it last? Why did it end? What did you like/dislike about him?

Okay, okay, don’t get jealous when she is talking about ex-boyfriends, you’ve got ex’s too. You don’t have to compare her ex’s to yourself. This is great info on what she likes in a relationship and what she doesn’t. Plus, it will tell you more about how she views serious relationships.

6. Have you ever cheated on someone before? What happened?

This one is a land mine, so be careful. That being said, it’s a great bit of information to know. I may be wrong on this one, but I think there is a reason people say once a cheater always a cheater. Has she cheated on more than one boyfriend? Well, there is a good chance she’ll cheat on you. The same goes for you. I don’t think the rule applies only to women.

7. How much time did you usually spend with ex-boyfriends? Did you think it was too much time or not enough time? What did you typically do with your ex-boyfriends?

Okay, one more time. Seriously. No getting jealous over ex-boyfriends. Don’t be that guy.

These questions basically let you know how much distance you should be giving her. Some guys like their girlfriend to be around all the time, and some don’t. Same with girls. Some girls like spending as much time with their boyfriend as they can, and some prefer having some distance. It’s just a personal preference.

Just like most of the questions, if your answers match up, that’s great. If not, well, it’s something to keep in mind. Don’t smother her and don’t give her the cold shoulder.

Questions about her

These questions are all about what she likes. You can keep these in mind to make her happy, or you can see how they compare with your likes and interests.

8. What are the three most annoying things a boyfriend can do? How about the three best things?

Things that annoy her = don’t do those things. Things she likes = try to do those things.

9. What was the most adventurous/crazy thing you have done in the past month? What is the most adventurous/crazy thing you have ever done?

This one will tell you how risk seeking or risk averse she is. If she is a lot more risk-seeking than you, you might have to expand your comfort zone. If you are more risk-seeking than her, be prepared for the fact she might not want to go with you on adventures. And she might not want you to do risky things either.

10. Do you prefer being outdoors or indoors?

Is she the indoor type, and you’re not? Don’t expect her to enjoy being dragged out on camping trips. She the outdoor type and you’re not? Better get some hiking boots. If you are both really different, maybe try compromising and making cabin trips.

11. What three objects that you own do you value most?

This one you’ll have to read a bit into. Is it something sentimental? She probably has a strong sentimental streak. Something practical? She probably isn’t very sentimental. Is it something expensive or something she can show off? Get ready to say goodbye to your money.

This one is also great because it’ll help you get some gift ideas for later. Or at least gift categories. Sentimental, get her something that reminds her of your relationship. Practical, give her something that will help with her hobbies. And so on…

12. What would you do if a close friend started saying mean things about you?

This question lets you know how she deals with conflict. Is she a peacemaker? Does she escalate things? Does she just avoid it?

Chances are she’ll deal with conflicts the same way with you. Maybe she’ll try to make peace, maybe she’ll get furious, maybe she’ll just stop talking to you.

13. What are your three favorite movies and three favorite TV shows? How about your three least favorite movies / TV shows?

This is a surprisingly practical question that will let you know how much you two will enjoy going to see movies together and watching shows together.

Does she watch shows/movies with you that are way out of line with her favorites? She might just be humoring you and watching them because you like them. If that’s the case, she’s probably going to get tired of humoring you and start wanting to watch what she actually likes.

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

This one will let you know what she likes to do. Sure she’ll probably do what you want to do for a few Saturday nights. Still, eventually, as the relationship continues, she is going to want to do what she wants to do. So if you like partying and she doesn’t, or if you like chilling and playing video games and she likes going out. Well, that’s going to be a problem.

Questions about sex

If you are in a place in your relationship where you are comfortable talking about sex, then these are some great questions to learn more about who she is sexually. If your relationship hasn’t progressed that far, don’t worry about it, just skip these.

15. How many sexual partners have you had? Have you ever had unprotected sex?

Yep, these are some pretty basic questions to ask your girlfriend, but they are pretty crucial to know. She’ll want to know the same. Tit for tat.

And remember, don’t get all pouty about her answers if she has had a lot of sexual partners or if she has had more than you. It’s not a competition. And besides, you probably want a girlfriend that enjoys sex as much as you do.

On the flip side, if she hasn’t had a lot of sexual partners, it might mean she isn’t so into sex, or it might mean she isn’t as experienced in the bedroom, or it might mean she doesn’t like to have sex until the relationship is a bit more serious.

Basically, you want her sex drive to match yours, whether you are really into having frequent sex or if sex isn’t very important to you.

16. What two things would you like more of while having sex? Is there anything you’d like to try in the bedroom that you’ve been afraid to ask for?

Good sex life is important for a healthy relationship. You should both be trying to make each other happy in the bedroom. But don’t feel pressured to try something you aren’t comfortable with. And don’t pressure her into trying something she isn’t comfortable with. If either of you isn’t enjoying the sex you’re having, it will end badly for both of you.

17. How often do you like having sex?

This question will help you see how well both of your expectations about the frequency of sex match up. Usually, if one person in a relationship has a vastly different number, it’s a bad omen for the relationship. But you can try talking through it and trying to find some middle ground. Just don’t try and force the issue. You’ll just have to decide how important sex is for the relationship.

18. What time of day is the best for sex?

This one will give you a good idea of what time of the day she will most likely be in the mood. Good intel for sure.

Questions about money

Money. The number one starter of fights in a relationship. These might not be the most exciting questions to ask your girlfriend, but they are enormously important.

19. How good are you with budgeting money?

At least one of you should be good with money. If you are both terrible with money, one of you will need to work on your money management skills. And you should probably decide who if you are in a serious relationship or live together.

20. What do you think is worth spending extra on getting the best?

This question will let you know what type of stuff she’ll be spending money on in the future. It can also let you know what she values.

21. What do you think is a waste of money?

This one will tell you what she’ll get angry about if you spend money on it.

22. What is the best thing about money: it provides security, it allows you to create good memories, or it will enable you to buy nice things?

This question will let you know if she is a saver, values experiences, or values objects. Do with that knowledge what you will.

23. In a relationship, when should a man pay for something, when should a woman pay something, and when should they split the cost?

This one is mostly for new relationships, but really good to know what kind of expectations are on the table.

So there we go, those are my questions to ask your girlfriend. Hopefully, they’ll help you out and give you some useful info about your relationship. Just remember, as I said before. None of these questions is a relationship sinker, just keep in mind what is most vital for you in a relationship.

More questions to ask your girlfriend

Here’s a list of some more questions you can ask your girlfriend. No commentary here, just a list of questions you can browse through and pick the ones you like.

  1. If you could become a master in one skill, what skill would you choose?
  2. What’s the most ridiculous reason someone has gotten mad at you for?
  3. What’s the best way to spend a rainy afternoon?
  4. What piece of clothing do you always get a lot of comments on every time you wear it?
  5. What’s the worst part of your average day?
  6. What would be the worst flavor of ice cream?
  7. What does a day in the life of a couple with a super healthy relationship look like?
  8. What was the most thoughtful gift you ever received?
  9. If you learned that your country was going to cut off all access to the internet at 12 am tonight, what would you spend your time/bandwidth downloading?
  10. What would a sitcom about your life be called?
  11. What’s your favorite thing to do when the power goes out?
  12. How good are you at keeping plants alive?
  13. What are some unwritten rules in your family?
  14. What do you geek out about?
  15. How are you? Like really.
  16. What do you know that you aren’t supposed to know?
  17. What are some clever insults you’ve heard?
  18. What book has had the biggest impact on you?
  19. What’s the most surprising thing you’ve learned recently?
  20. What’s the saddest movie you’ve ever seen?
  21. Where was your favorite place to play outside of your house when you were a child?
  22. What mistakes in your life have you learned the biggest lessons from?
  23. What’s the most important thing you learned from your parents?
  24. What would your ideal life look like?
  25. What 30 seconds would you erase from your life if you could?
  26. What’s the funniest lie you’ve heard someone tell?
  27. Who do you think has it all figured out?
  28. What slang or trend makes you feel old?
  29. How hard do you work to improve yourself or your life?
  30. When was the last time you went to an amusement park or fair?
  31. What’s your idea of succeeding?
  32. What horror stories do you have from your job?
  33. What’s the most embarrassing clothing malfunction you’ve had?
  34. What’s the worst non-illegal habit a person can have?
  35. What scene from a movie had a dramatic impact on you as a child but probably wouldn’t faze you now?
  36. What childhood movie was ruined after you watched it again when you were older?
  37. What do you think about when you are lying in bed, unable to sleep?
  38. If you could ask one question about your future, what question would you ask?
  39. What would you like your last meal to be?
  40. What’s something you’ve been wanting to get off your chest for a while?
  41. What’s something that many people find unattractive in a person, but you really like it?
  42. What causes you to look down on someone?
  43. If you were tasked with creating a brand new, wildly entertaining sport, what sport would you create?
  44. How good are you at keeping secrets?
  45. If you were a master reverse pickpocket, what would you put into their pockets?
  46. What do you look forward to?
  47. What’s the worst downward spiral you’ve ever witnessed?
  48. What’s the best thing you own?
  49. How artistic are you?
  50. What popular shows or movies have you not seen?
  51. What salad dressing probably doesn’t exist, but it would be amazing if it did?
  52. Would you get into a relationship with yourself? Assuming that “other you” is a gender you are attracted to.
  53. What is the most terrifying thing you can imagine?
  54. What are some things you’ve seen that you wish you could unsee?
  55. Where is the best place to go to meet awesome people?
  56. What are some things you could never wrap your head around?
  57. What are some things you are below average at and some things you are above average at?
  58. What would your dream home look like?
  59. How often do you dance?
  60. What’s the most romantic thing you’ve heard about someone doing for someone else?
  61. What do you need to vent about?
  62. Hammock, bean bag chair, or regular chair? Why?
  63. What would be the perfect pet?
  64. What really should be common knowledge, but for some reason, isn’t?
  65. What’s something way better than you thought it would be?
  66. What do you wish you had started a long time ago?
  67. What’s your favorite foreign film?
  68. What do you wish you could change about yourself?
  69. What are some things you feel compelled to do?
  70. What’s a good relationship tip that sounds like a bad tip?
  71. When are you most comfortable?
  72. What food do you crave most?
  73. What’s the most disgusting or terrifying story you’ve ever heard?
  74. What strange food combinations do you enjoy, and which do you hate?
  75. What are some of the most annoying things that happen on social media?
  76. What’s the best topping/ice cream combination?
  77. What’s your favorite euphemism?

Things to watch out for

These are some essential things to keep an eye out for. Especially when you are just starting to date a girl. They are red flags that you’ll want to investigate a bit further before you get too serious.

Watch how she treats waiters and waitresses.

If she is mean to them, she probably has a mean streak that will come out to bite you in the ass. The best way to judge a person’s kindness is how they act towards people they don’t need to be nice too. Plus, who wants spit in their food?

“I hate drama, but drama always finds me.”

Nope, she loves drama. And she probably goes out of her way to create or encourage it. Be prepared to always have some kind of drama emergency going on.

She hates your hobbies.

She won’t start liking them. You’ll either need to end it or stop doing the things you like. Find a girl who likes the same things you do. Or at the very least find a girl who tolerates your hobbies because she knows they are important to you.

✍️  May 14, 2020

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