21 Questions to Ask a Guy – Questions to Ask a Friend

Girl, it’s easy to love me now, would you love me if I was down and out? If I fell off tomorrow, would you still love me? If I didn’t smell so good, would you still hug me? Those are some of the lyrics of 50 Cent’s 21 Questions but that’s not just what this post is all about. In fact this post is about that and more. So lets assume you just met this guy and really like him but you are not sure how to get started, how to know him more, we have put together series of 21 Questions you can ask him to either know him better or to just engage him in a conversation

These questions are random and in no particular order. You can start from anyone depending on the circumstances. In addition to these 21 questions, we have added a collection of further questions that includes Intimate Questions to Ask a Guy, Fun Questions to Ask a Guy and Interesting Questions to Ask a guy. You can check our Questions to Ask category for more questions. So lets get started with 21 Questions to Ask a Guy.

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1. What are the things that attract you most to any lady? – Now be open to these question and don’t take it personal. While most question will easily say things that you possess just to make you feel happy and admired, some will be blunt. They might be telling the trust or simply trying to see your reaction. In any case, their answer can be a pointer to their character. If all the qualities that attract them to a lady is all physical then use that information in your judgement.

2. If you have the opportunity to date any celeb who will that be and why? – This is a straight forward question but an engaging one. It tells of his preference and further reveal their secret fantasy. If you want to be dirty with this (if the condition is right) you can ask “If you have the opportunity to have sex with any celeb who will that be?

3. What do you want in a relationship? – Now this is a date question, if you are just getting to know the person and nothing romantic in view you might skip this question. However if there is chance of a romantic relationship in view then this question is a perfect one as it gives you a peep into his future expectation.

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4. What kind of music do you listen to and what’s your favorite song? – Music is part of everyone and a person’s choice of music tells a lot about their personality. You can also take this further by asking if he has to choose one song to listen to for the rest of his life what song that will be.

5. What is your favorite movie and what movie are you not tired of seeing? – This is a standard question. You can asking it in a casual conversation or in a dating scenario. You can also find out his favorite actor and actress.

6. Are you into sports and what’s your favorite sport? – Most guys are either fans of football, basketball, baseball etc. Asking about his favorite sport opens up a whole new conversation that can lead to discussing his passion or goals for the future. You can take this further by asking of his favorite team.

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7. What’s your favorite book and if you have to recommend a book for me to read what will it be? – Now some people don’t enjoy reading but they like to be considered smart. So you are sure to get a book recommendation and even beyond that.

8. Do you believe in love at first sight and have you ever experience it? – Love at first sight is right and most people have probably experienced it. This question is a good way to get started if you are looking for a romantic connection.  It’s fun to talk about and you both can end up talking more about your view on love and relationship.

9. What’s the funniest way a girl has asked you out? – This is a funny question and strictly to lighten the mood. You can take this further by asking if a lady has ever made any sexual advances on him and what did he do.

10. If you could change anything about your life what would it be? – Everyone has some certain things they don’t quite like about their lives. This question is designed to dig deep into his insecurities, fears and hope. You can take it further by asking why?
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Intimate Questions to Ask a Guy

11. Has a lady ever broken your heart before OR Have you broken a lady’s heart before? – This is an intimate question and it’s answer is something you have to pay close attention to if you are interested in going to a romantic relationship with him. While most guys won’t confess to cheating on their girlfriend, they’ll readily admit being a victim of a heartbreak.

12. Have you ever had a one night stand? – One night stand is a secret fantasy for most guys so don’t be surprise with a “yes” answer. You can take this further by asking why and what happened with the lady afterwards.

13. What do you do for a living? – This is an intimate question and one most guys might hesitate to answer. The reason is because what a man does for a living is personal to him. If you can get him to talk freely about his job, then he’ll open up to further question.

14. What do you enjoy doing? – For most people, what they enjoy doing is quite different from their job. They’ve not quite figure out how to make money doing what they love. Another way to phrase this question will be “If money is not a factor, would kind of job would you rather be doing?

15. Who is the closest person to you? – This also can be phrases as “Who do you trust most in your life” This question is design to give you an insight to whom he respect the most. Someone you can talk to should you need to get through to him or get him to see things from a different perspective.

Funny Question to Ask A Guy

16. What’s the weirdest dream you have ever had? – Everyone dreams. Asking about his weirdest dream is a fun way to get him relax around you and turn a past situation into fun. You can take this further by asking him if he has ever been chased in his dreams.

17. What is the worst lie you’ve ever told and did you get caught? – Guys lie, some all the time. Some lies are just plain stupid so expect something funny. You can take this further by telling him your own worst lie and what happened afterwards

18. If you’ve have an opportunity to be invisible for one day, what would you do? – This bring a lot of imagination to bare. It helps stretch a conversation and also gives you an insight to his humor side. You can again take this further by asking him what good will he do.

19. If you were a lady what kind of guys will you be attracted to? – Well, most guys will give you the quality the possess as the kind of guys they’ll be attracted to. Pay attention and again you can take it further asking why they find those qualities attractive.

20. Which would you rather be, ugly and smart OR dumb and handsome? – Again pay attention to his answer as it gives you and insight to his preference. You can also take this further by reversing the question. Which would you go for, a ugly and smart girl OR a beautiful but dumb girl.

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Questions to Ask Your Boyfriend

Asking questions to your boyfriend is a lot different from a friend or someone you are just getting to know. Questions in relationship not only serve as an avenue for effective communication but give both party the opportunity to get to know each other better. While each conversation does not have to be intense and serious, we have put together these further question specifically for asking your boyfriend. Some of these are serious questions while others are as a way of conversation. Here are some questions to ask your boyfriend.

1. What motivates you? – Your boyfriend is not like every other person. It’s your duty to not only be his girlfriend but also support him. Asking what motivates him in life gives you an idea of how to support his goals and dreams.

2. Why did you break up with your ex girlfriend? – Your intention is this regards is not to judge but to be in the aware. Most times mistakes are repeated when people don’t take time to analyze where they got it all wrong. Knowing his best past relationship will help you avoid any unexpected intrusion.

3. Do you have any secret you think I should know about? – People have secrets and sometimes are not up front in a relationship situation for fear of being judged.  Asking him if there is any secret you need to know gives him the opportunity to come clean.

4. Is there anything you’ve done in the past that you are not proud of? – No one is perfect and some of us have done something in the past that we are not particularly proud of and wish we can undo. This question give more room for intimacy between both of you.

6. What makes you insecure? – We all have our insecurities. Finding out what makes your man insecure can put you in a position to assist him. You can also take this further by asking him what makes him jealous in a relationship.

For more questions visit our Questions to Ask Category.

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