50 Personal Questions to Ask a Guy

Asking questions is a great way to know a person. This is especially true of guys since they rarely go out of their way to share their personal life with their partners. so whether you have just started dating a new guy or wish to get to know him better before moving ahead, here are fifty personal questions to put to your man.

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1. Who are your closest friends? This is a nice way to begin since it lets your guy discuss things in his comfort zone while not moving too ahead too soon. Moreover the answer can also tell you a lot about the kind of person he is. For instance if his closest friends are all from high school, it indicates that he values loyalty in relationships and is wary of change.
    
2. Do you have any phobias? This is again a personal question without seeming like you are interrogating about his love life.
    
3. That hairstyle/outfit really suits you. Where did you get it? In all probability, your date knows that you are not terribly interested in where he does his shopping. But just the fact that you noticed something nice about him and asked about it would make him really happy.
    
4. What is the best vacation that you took? People usually love talking about holiday they took in another country or the roaring time they had on the beach over the weekend. Encourage your boyfriend to talk about what he liked most of all on that particular vacation and you might get an insight into his favorite kind of getaway.
    
5. If you get the opportunity to turn into a girl for a day, would you take it? This question is personal while being fun too - If he says yes, ask him why and if no, ask that too.
   
   
    
6. Who is your favorite family member/sibling? This question offers a safe way to know more about his family. If he comes from a supportive family, he will probably tell you a good deal about his parents, siblings and even cousins and grandparents. But if he appears vague and wishes to change the subject, then it would be best not to prod him more since he might have had an unhappy childhood.
    
7. Do you like to talk dirtily on the phone or online? This again could get fun and maybe even hold cues to what turns him on.
    
8. What about your pet peeves? You may be surprised at the number of unexpected things that may crop on this one – breadcrumbs in bed, sinkholes clogged with hair, Lindsay Lohan stories in the media, weekend traffic on the way to his family home, lizards… the list could go on.
    
9. What was the worst lie that you told your parents? This could offer another precious peek into his childhood; extend the discussion by asking if he was caught and if so, how.
    
10. If you could play a part in a movie, what would it be? His answer might be the dashing Rhett Butler in period classic Gone With the Wind or a more cerebral character like John Nash in A Beautiful Mind . Whatever it is, the reply would surely allow you a tiny peep into his fantasies.
     
11. What is your happiest memory from the past? Most likely it will be an account of a childhood picnic or an afternoon at the zoo when he was seven. However if he has had an unhappy upbringing, he might talk of the time when his science project was appreciated at school or he bunked class to catch a movie.
     
12. How do you spend your week? This question is particularly useful when you just getting to know him. finding out what someone does during non-working hours would give you an insight into his priorities. For instance your date might put in a 40-hour week at work, but if he still has the time and energy to hit the gym thrice a week, you know that health and fitness score high with him.
     
13. Do you ever feel the need to have total privacy? If yes, when? this again is likely to let you have a peek in his daily personal life.
     
14. What are the things that you like to do alone? continue the conversation about his personal life with this question.
     
15. How would you describe your version of a perfect home? This again is likely to grant you an insight into his dreams and priorities.
     
16. If one song were to describe your life, what song would it be? this kind of questions delves into his personal favorites without seeming too intrusive. also you are sure to have a fair idea about his past and present.
     
17. Ask your guy to name five new things he would like to learn before turning forty/fifty/sixty - Discussions on future make very interesting conversations, though you may need to tread lightly on touchy issues like kids or finances
     
18. Workwise, where do you see yourself in another ten years? Even though this may sound too much like being interviewed for a job, it will give your date a chance to talk about his professional ambitions and aspirations for future.
     
19. If you could only achieve one thing in life what would it be? this question narrows the focus on his goals for the future and is sure to acquaint you with what he really holds important in life.
     
20. When upset, what do you usually do to feel better? This question may be venturing into serious areas but it could be useful for getting a glimpse of the person within.
     
21. What was your last relationship like? once you have got comfortable with the personal nature of questions, it is time to delve into his love history.
     
22. How and why did your previous relationship come to an end? Follow up the former question by asking him to elaborate on what ended the last relationship.
     
23. What did you think of me when you first saw me? use this question to shift the focus on happier things like his present partner - you.
     
24. If you could redo any past moment what would it be? this is a good question to put to a guy if you are not yet a couple or even officially dating.
     
25. What is the strangest habit you have ever had? – another fun question that lets you get personal without coming on to him directly.
     
26. If you had to rank your own sex appeal on a scale of 1 to 10, then how would you rank yourself? this question lets you get back on naughtier ground without seeming desperate for his attentions.
     
27. Have you ever had a true one-night stand? yet another question that relates to his love life – just be warned since it could bring up quite a few surprises.
     
28. Do you like kissing in public? Such questions are the staple of some delicious flirting – a bit personal but not offensive.
     
29. Are you a virgin? if you are confident of pushing the envelope still further, by all means go ahead with this question.
     
30. When was the last time you planned a surprise party for someone? This might make for a hilarious set of memories but don’t get unnerved if your guy mentions that the last one he did was for his ex.
     
31. Ask about the yuckiest thing he ever had to do. It may be something from their high school chemistry class or the first time they got completely sozzled with friends but no matter what it is sure to inject some humor into your conversation.
     
32. Describe an erotic fantasy that you have. However remember to keep the question light and fun and don’t bring an element of stress by expecting the other person to act anything out.
     
33. If the two of you could just drop whatever you are doing and do something fun, ask your guy what would it be. This would be an interesting way of knowing what he enjoys doing most, especially in your company.
     
34. Tell me about one of your most embarrassing moments. It could be the time when he got drunk and threw up at a friend’s bash or got his ex’s mom’s birthday wrong.
     
35. Have you ever kissed a man? this is cheeky, fun and allows you a quick peek into the guy’s fantasies.
     
36. Would you prefer a candlelight dinner to a fun party with college friends? such personal questions are a fun way to gain insight into a guy’s romantic preferences.
     
37. Describe the type of relationship you want to have for the rest of your life? this naturally gives you an idea whether you are destined to fill the role or if you are already dating him, what is expected of you
     
38. What was the first thing that attracted you towards me? if you both are officially a couple, this is a question that is both cute and personal.
     
39. What would you have said if I had asked you first for a date? this question is naturally for situations where your guy has made the first move.
     
40. Did anyone help you figure out how to ask me out on a first date? like the previous question, this again lets you both happy memories of a shared past.
     
41. Which was the moment when I impressed you most? this is a far more direct question and may take your guy a moment or more to answer.
     
42. What you don’t like about me? this might require a strong stomach to digest so go ahead with caution.
     
43. If you had to rank how attractive I am on a scale of 1 to 10 then how would you rank? Same as above, so be forewarned.
     
44. What body part that you like in me most? if you both feel comfortable, use this question to venture into more intimate territory.
     
45. When I don’t express it, how do you know I want to make love to you? such questions could set the stage for some delightful foreplay.
     
46. What would you like to do to me? Look deep into his eyes when you put this question to your guy.
     
47. What would you like me to do to you? Ideally run your fingertips down his face and neck, as you put this question to him.
     
48. Would you prefer the lights on or off during sex? You can ask this either while setting the stage for intimacy or even in the thick of some amorous action.
     
49. What do you need from me to make you feel more loved and cherished. This is sure to act as a fitting finale to your romantic episode.
     
50. Should we do this some other time? The answer to this of course will determine whether you get to put any more questions to him in future.