100 Questions to ask a guy before dating

By: Naveen B

Have you ever asked yourself “what questions to ask a guy before dating” There’s no doubt that men have different personalities in comparison to women.

You might wonder, what do men want? Is he emotionally and financially ready for a committed relationship? 

When it comes to the beginning of a relationship with a guy, it’s quite common for girls to worry about such questions

You’re just not sure if a guy is right for you. You’re not sure if he really makes an effort to keep your trust and love in place. So, it’s better to be prepared and ask him directly before allowing yourself into anything serious.

Here are 100 questions to ask a guy before dating him. These questions will help you better understand a guy and his intentions. Get ready to be amazed.

100 Questions to ask a guy before dating


Here are Top 10 Questions to ask a guy before dating

1. Who do you live with (parents, family members, roommates)?

If they live with their parents, that might mean you can’t see them very often in order to have time alone.

If they live with roommates, they may feel pressure from friends to hang out all of the time. 

Again, it’s not always easy to have these discussions, but knowing what you’re getting into upfront can save a lot of heartache down the road.

And also it’s the best way to know if he prefers to stay alone or with people all the time.

Also read: 100 Questions to ask yourself before dating and falling in love with someone new

2. Where did you grow up and what was your childhood like?

If you consider these questions to ask a guy before dating, this will give you an idea of his family background and culture, which can influence everything from his career path to who he chooses as partners.

So, it’s better to know as much information about him/her as possible before you start dating because it can help to make your relationship stronger.

You’ll also learn more about him by asking questions to ask a guy before dating so don’t hesitate!

3. Are you emotionally available for a serious relationship?

The answer to this question is important because it tells you whether or not he’s ready for commitment.

It also helps you assess how much emotional baggage he has – baggage that could potentially cause problems down the line.

However, just because someone isn’t ready for commitment doesn’t necessarily mean they aren’t good boyfriend material; it just means you need to wait until the timing is right before trying anything too serious.

4. How do you approach disagreements and conflicts within a relationship?

No matter how perfect two people seem together, there are bound to be arguments and issues that arise over time.

It’s important to get a sense of how your partner deals with conflict before entering any type of long-term commitment.

This way you will understand what kind of person you are dealing with, his values and expectations for your future.

Also read: 21 Online dating questions to ask before meeting

5. Have you ever been in love before?

The answer to this question is important because it tells you whether or not he’s had deep, meaningful connections with other people.

But even if he hasn’t loved anyone else before, it could mean you might be lucky enough to experience her first love now.

Also, when it comes to love, nothing is worse than waiting around wondering if he loves you when you already told him how you felt.

That’s why it’s essential to make sure he knows your intentions early on in the relationship.

6. What do you do for a living and what are your goals and plans for the future?

There are many reasons to find out what a guy does for a living. For one, you want to make sure you are on the same page financially.

Secondly, if he’s just graduated college or working entry level jobs you want to be aware of the possibility that he may move away at some point.

Lastly, having different lifestyles can lead to incompatibility down the line. So, it’s better to be prepared for what the future might hold.

7. Why did your last relationship end, if you had been in one?

The response to this question is crucial because it can tell you a lot about what your partner’s expectations are for the future.

If he broke up with his ex because she wanted to settle down and he didn’t, that can be due to compatible and understanding issues.

On the other hand, if they broke up because of infidelity, you should take this as a warning sign about your potential relationship.

The key is to listen closely to what he says and be mindful of how he reacts in certain situations.

Also read: 100+ Questions to ask before dating (very intuitive and thoughtful)

8. Do you consider yourself romantic or analytical?

It’s vital to be with a partner whose personality meshes well with your own. Some people are naturally more romantic and others are analytical.

Therefore, it’s important to find out what the difference is between you and your partner before committing to a relationship. Is he as romantic as you?

Or maybe he looks at everything as logical and driven by rational thoughts, whereas you are a bit of both?

These are things worth thinking about because they can really affect the quality of your relationship down the line.

9. What’s your stance on cheating and have you ever cheated in your previous relationships? 

Cheating is not something that is easy to admit to, and it’s understandable if your date feels uncomfortable talking about it.

Still, if you have strong feelings for your date, they may be able to offer valuable insight into their character as well as their stance on cheating.

10. Are you looking for marriage or just a fling? And what do you think is the key to a happy marriage?

Would you rather have a casual or committed relationship? Marriage isn’t an option for some guys, but those who are interested in marriage are more likely to be emotionally stable and invested in the relationship.

Also, asking your potential partner what they think constitutes success in marriage is one of the most crucial things you can do before taking things too far down the road.

Also read: 500+ Dating Questions: Conversation starters topics for online, first & second date nights

Deep Questions to ask before dating a guy


Here is a list of deep questions to ask before dating a guy:

11. How much does physical appearance matter to you?

12. Do you prefer long distance relationships?

13. Are you afraid of love?

14. Where should we meet on the first date?

15. Do you believe in having an open relationship with multiple partners?

16. What makes relationships work even in conflicts?

17. When does a relationship move from being just physical to a more serious commitment?

18. What is your definition of cheating on your partner?

19. When did you feel that I am the one for you?

20. What makes you feel insecure?

Important Questions to ask a guy before dating


The following is a list of very important questions to ask a guy before dating:

21. How often will we see each other?

22. What are your views on feminism?

23. How long is your daily commute to work?

24. Have you ever been married before?

25. How many kids do you want to have in the future?

26. Is there anything that I can do to get over my fear of opening up and letting myself fall for someone again?

27. Do you think people who date around will eventually settle down?

28. Have you been faithful to any of your past partners?

29. Have you cheated on anyone in the past, and if so, how would you react if your partner cheated on you?

30. What’s the difference between lust and love?

Good Questions to ask a guy before dating him

These are some of the best and good questions to ask a guy before dating him:

31. What is your favorite season and why?

32. What is your birthday?

33. What is your sign?

34. What was the last gift you gave someone and how did they react to it?

35. What’s your professional background? and how much do you make?

36. How would you describe your sense of humor?

37. What job makes you happy?

38. What is your biggest regret?

39. If you could change anything about your past, what would it be?

40. What is your favorite music genre?

Interesting Questions to ask a man before dating


Here is a list of interesting questions to ask a man before dating:

41. If you had to sacrifice your love life for your career, which would you choose? Why?

42. What drives you in life?

43. What is the major problem you have right now and how do you deal with it?

44. Do you strive for efficiency or harmony?

45. What is your favorite and least favorite household chore?

46. What are your plans for the future?

47. What are your pet peeves?

48. What food can you not stand?

49. Is there any food you can’t live without?

50. What is your idea of a perfect romantic evening?

Best Things to ask a guy before dating him


Here is a list of best things to ask a guy before dating him:

51. What are your views on kids and pets?

52. What is the most embarrassing thing you’ve done recently?

53. What are your three best qualities?

54. What are your three worst qualities?

55. Do you like your partner to be mature or childish?

56. What is your definition of love?

57. What is your definition of commitment?

58. What does having trust mean to you?

59. What does respect mean to you?

60. What does faithfulness mean to you?

Questions to ask guys before dating to get to know them better:

Here is a list of questions to ask guys before dating to get to know them better:

61. What do you do to gain someone’s respect, love and trust?

62. What is your favorite movie?

63. What do you want out of life?

64. Tell me something that no one else knows about you

65. What are your views on monogamy and open relationships?

66. Which of my questions did you find the most interesting and why?

67. Can I get a picture of you?

68. What’s your stance on women’s rights?

69. What’s your political party affiliation and why do you support them?

70. Are you comfortable with phone calls or video calls or chatting?

71. What is your view on animal cruelty?

72. Where do you like to live the rest of your life?

73. What’s the meaning of life to you?

74. What makes you feel secure and loved?


Sexual questions to ask a guy before dating

Here is a list of dirty and sexual questions to ask a guy before dating:

75. What are your measurements?

76. When did you lose your virginity and with whom?

77. How many people have you slept with?

78. When was the last time you had sex?

79. What’s your size?

80. What are your personal views on sex before marriage?

81. What’s your favorite position?

82. What turns you on?

83. How dirty is your mind from the scale of 1-10?

84. Wouldn’t you date me, if I am not a virgin?

Serious Questions to ask him before dating

Here is a list of serious questions to ask him before dating and committed to him:

85. How important is money to you?

86. What are you looking for in a relationship?

87. Are you someone who is easily jealous or does that just not come naturally to you?

88. Do you feel like an introvert, extrovert, or ambivert?

89. Do you have any religious beliefs and if so, how do they affect your relationships with other people?

90. When was the last time you were single?

91. Is there anything from your past that would be a deal breaker for us as a couple (i.e., cheating, abuse)?

92. How do you think we will make this work when we live hours away from each other?

93. What is one of your favorite movies and why?

94. Who has been the most influential person in your life, and why?

95. What’s your biggest pet peeve?

96. What are three qualities you find attractive in a partner?

97. What’s your idea of the perfect date night?

98. Where do you see yourself five years from now?

99. Why should I be attracted to you in the first place?

100. Tell me about a time where you felt really proud of yourself

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Experienced Psychology and philosophy Writer, self-help and relationship Coach and thought influencer. He has 7 years of experience in Personal development industry. His expertise as a self-help and relationship Coach has been highlighted through his articles in medium and substack to name a few. To be updated with his latest work, connect with him by following his social media accounts.

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