Questions to ask a guy – 180 Good Questions to Ask

Conversations can be difficult to start. There's a reason small talk is so popular. When you are on a date with someone you love, the last thing you want to talk about is the weather. There are many good questions you can ask a man to spark a conversation and keep you both engaged.

These questions are great for when you're still getting acquainted with someone. For example, if you're going on a first or second date with a guy and trying to learn more about them. These questions are great to remember even if you've been together for a while and don't have much to share over dinner. This will allow you to get to know each other better and open up the possibility of having more intimate conversations. Some questions can be funny or flirty while others are more serious and personal. 

If you are a chatty girl, it is likely that you are with someone who likes to listen to you. This means that you have probably heard him speak when you agree with one of his big ideas. He might be uncomfortable contradicting you, especially if you don't know each other well. You might hear, “I want a house that has a lot of land and quiet.” He might be thinking about how he would never want to mow more that a quarter of an acre.

What Questions to Ask a Guy?

Questions to ask a guy
Boy and girl talking and eating sushi

You spend a lot time together when you are dating. While you can have endless conversations about your work, family, friends, or other topics, it is nice to occasionally mix things up. 

We love our partners and want to learn everything about them. We want to learn about their hopes and dreams, as well as what they ate for breakfast. While our boyfriends are able to answer straight questions, it can be fun to ask them a question that they don't expect.

This is where the list comes in. This list will help you have a more meaningful conversation with your partner and reveal a lot about them. Although you can talk all day, you rarely get to know the real you of the person you love.

These are some questions you can ask a man if you feel stuck.

1. What would you do if you were given a billion dollars?

2. Which chore is your least favorite?

3. What is the one thing you procrastinate about?

4. What do you think of the perfect vacation or how would you spend your time?

5. Are you a parent?

6. How was your childhood?

7. Are you looking to have children?

8. What was the longest lasting relationship you had? What was the reason for it ending?

9. Are you married or engaged? Are you interested in getting married?

10. Are you a married couple?

11. What is your opinion on religion and spirituality?

12. What do you think about gay rights?

13. Are you adamant that money cannot buy happiness?

14. What's your dream job?

15. What is the one thing you would like to do in your life?

16. Which achievement are you most proud?

17. What are your fears? When was the last time that you voted?

18. What would you say about your relationship to your family?

19. Do you have a best friend or a partner?

20. What is your love language?

More Engaging Questions to ask a guy

21. Which was your favorite moment at the mic?

It's hard to find someone who doesn't enjoy telling a great story about themselves. This will allow your guy to tell you a story about himself and it is a great way for him to talk. This will let you know his interests and priorities.

22. What is your favorite childhood thing?

Everybody has things from childhood that they still have. Although he might not be able to admit it, he may still enjoy building sand castles and peeing in snow. You're likely to get some adorable answers to this question. You don't need to limit the question to one childish thing. He can list many more.

23. What is your biggest doubt?

All of us have doubts. No matter if those doubts concern the world in general or our own lives. This can lead to serious conversations, but it can also be a great way to build a strong relationship between people.

24. Who has totally lost your respect?

This is a great question to ask your son about his values. This is a great question to start a conversation, as there are many celebrities who have fallen from grace.

25. Which movie would you like to see your life be more like?

Another fun question to answer is “What would you change?”. This creates a unique conversation. Talk about the little things that could be changed. You can really dive into the everyday changes that would occur if your life were more like the movie. You don't have to be ridiculous.

26. How many phones are you missing or broken?

Sometimes a simple question can turn into a long conversation. Because behind every lost or broken phone is often a story. Or he may be super clumsy, forgetful, which can also be a good thing to know.

27. Who or what are your nemesis(s)?

Everyone has people or things they hate. He probably does, too. This is a great question for starting a conversation about your annoyances. You can also encourage silly or funny answers, such as jars that won't open, or YouTube videos that load ads flawlessly but not the video. It's easy to shift the conversation to something lighter, such as a rant about annoying things.

28. What is the most ineffective thing you can do?

Is he hiding any hidden talents? This is great as he will often be able to show you. You can now learn all about his silly and useless talents!

29. What is the worst thing and greatest about being a male?

What do you know about being a man? Now is your chance to learn more. You might be amazed at the answers that the guy you are speaking with will give you. It might be a good idea to move the conversation to discuss some of the more annoying aspects of being a man. This question is great because it's fun to answer, and you might learn some new things.

30. What is the biggest mistake most people make?

There are many answers to this question, so it is difficult to predict what type of answer he will come up with. It's a good question to start a conversation or bring up some common issues you can all commiserate on.

31. What would you do with 5 million dollars?

This is a great question to answer. It can also reveal a lot about your guy. It will reveal what morals he believes are most important and which activities he detests.

32. Which long shot did you take that paid off?

This question has probably never been asked before so give him time to think. He'll likely give you an interesting answer, either a story or fact.

33. What would you do if you had one magic trick that could do nothing but boring?

This is a fun question that can lead you to some very creative answers. Examples might include: unclog the drain, make your toast slightly browner, unjam a copier, and so on. The conversation could be furthered by thinking of the incantation that would accompany the spell.

34. It happens that you suddenly wake up in the middle of the night. What is the most frightening sound you could hear when you wake up?

This is great as it may give you an insight into his fears. You can either give him the opportunity to laugh, or you can ask him questions that will help you understand his fears. It's fun to ask guys this question and it makes it easy to follow up. Talk about how to increase the scariness, discuss his fears, or try to identify common fears.

Simple Questions to Ask a Guy

35. What is the most attractive thing about a woman to you?

36. What is the most absurd talent you possess?

37. What's the worst thing about you?

38. What can you do to relax after a stressful day at work?

39. What role model are you looking for?

40. Who would you like to meet most?

41. What's something you've never done well at?

42. What's the first thing you notice about a woman?

43. Which childhood memory is your favorite?

44. What are you most proud of?

45. Are you proud of something you have done?

46 What is the scariest thing that you have ever done?

47. Create the most delicious ice cream sundaes you can imagine.

48. What was a rule that you hated as a child and would you make your children follow?

49. Which was your favorite age?

50. Which date was the most embarrassing?

51. Are you a cat or a dog?

52. Which line is your favorite from a movie?

53. Which quality do you most value in mine?

54. What is your greatest fear

55. Who would you invite to a dinner party?

56. Which vacation is your dream?

57. What would you say to the president if you could?

58. Who was your first crush

59. Who inspires and motivates you most often?

60. What can you do when you don't want to sleep?

61. Can you tell me a thing that's big or small that no one else has ever told you?

62. What are the three most important things you would take with you if you had to move to a new county?

63. What is your pet's favorite memory?

64. What would you do if tomorrow was your final day on Earth?

65. What is the one thing that people wouldn't know about you if they just looked at you?

66. Who has totally lost your respect?

67. Which movie would you like to see your life be more like?

68. How many phones are you missing or broken?

69. Who or what are your nemesis(s)?

70. What is your favorite childhood thing?

71. What is the worst thing and greatest about being a male?

72. What would you do with 5 million dollars?

73. Which long shot did you take that paid off?

74. What would you do if you had one magic trick that could do nothing but boring?

75. It happens that you suddenly wake up in the middle of the night. What is the most frightening sound you could hear when you wake up?

76. Which was your greatest mic-drop moment in your life?

77. Are you tired of hearing the same old stories?

78. Which person made a lasting impression on you, but only for a brief time?

79. Which field would you consider your expertise in?

80. Which author is your favourite? Which book were you most fondly influenced by?

81. What habit do you want to quit?

82. What habit would you like to adopt?

83. What is your vice?

84. Is there a childhood memory that made you cringe?

85. Is there one thing that you remember from adulthood that made you cringe?

86. Which experience would you like to recreate?

87. What can you learn from past relationships or exes about yourself?

88. What characteristics do you look for in a future partner?

89. How do you relate to your ex-lovers?

90. What is your opinion on monogamy?

91. What secret identity would you use if you were a superhero?

92. Did you ever date someone that your family didn't like?

93. What is the worst injury that you have ever suffered?

94. What is the most frightening dream you have ever experienced?

95. Do you spend or save?

96. Have you ever thought of something silly until you actually tried it?

97. If you had to pick, which Kardashian would you choose and why?

98. Which holiday tradition is your favorite?

99. What is your space-out dream?

100. What is the one thing that you wish your mom would never learn about you?

Questions to Ask – Get to Know Someone

101. Which movie are you able to watch over and again and not get bored of?

You'll enjoy him telling you his favorite movie and you'll also learn about the types of shows and movies that he loves. It's easy to expand on this question because you can talk about your favorite movies and TV series, as well as the movies or shows that you don't like.

102. What would the design and contents of a treehouse look like?

This is my favorite question to ask a man. This question is pure creativity. It's great because it allows guys to have a bad-ass tree house all to themselves. It's something I don't understand, but I have never met a man who disliked tree houses.

103. Which trivia fact is your favorite?

You get to see some of his knowledge and he gets to share it with you. Ask him to share something that you don't know. It's a win-win situation.

104. Which celebrity would be the worst leader for a country?

This question is fun because you can imagine what the celebrity would do if they were leader, and what laws they would create. This is a great one for a good laugh. Keep the conversation going by switching between celebrities.

105. Was there anything you were really interested in when you were younger, but you now consider it silly?

Learn about the embarrassing things he did as a child. This ammo is great for some good-natured teasing later.

106. Which historical figure was not as remarkable as people believe?

I don't know if everyone is interested in history. Even if he isn't interested in history at all, he will probably enjoy this question. As they say, “Great men rarely make good men”.

107. You have the responsibility of making insects a favorite food item. To achieve your goal, you have 1 billion US Dollars. How do you do it?

Another one? It's amazing how quick he thinks and how creatively he solves problems. Although it is a somewhat random question, it can be a great way to discuss creative ideas. It's a great way for people to solve problems together and have a relaxed conversation.

108. What do you think that you know a lot but don't actually know?

Everybody likes to believe they are experts in many things. Let's face it, most of us are average or below average at almost all things. Think about how many people will claim to be above average drivers. It is always good to reflect on yourself.

109. What are we doing to make society laughable and ridicule in 20 years?

You'll have plenty to laugh about if you look back 20 years. It will be the same 20 years later. Many things that are now popular will be ridiculed and laughed at by people. What do you think the future you will view with disdain?

110. This double standard is absurd and must be stopped.

There are many double standards available. Now it's time for him to decide if he's interested in societal issues or not.

111. Which customer service experience is the worst?

He likely has more than one. Who doesn't love a bad customer service story? He'll have plenty of customer service stories if he has worked in the field. He probably has customer service horror stories if he hasn’t.

112. What is the best way for a government control its citizens?

Ok, so I debated whether to add this one to the list. This question is more complex and important than the rest. If you don't feel it is appropriate, please throw it out. If you're both interested in history or politics, it can lead to interesting conversations. 

113. What would be your top choice for a cause you'd like to dedicate your entire life to?

Each of us has causes we are passionate about. You'll now be able find out his cause. It will also tell you how active he has been in volunteering and charity. It's a great question because it allows you to compare what you are doing with your ideal life.

114. What would be your greatest achievement if you were to die today?

This is a great question to ask yourself. It is easy to lose sight of the fact that eventually we will die. It is important to remember that life is meant to be lived.

115 What can you do to make the world a better environment?

This question may have the same answer or not as question 34, but it is likely related to question 33. It's a great question that you can ask to learn about his life and what he considers important.

116. What are some people who you have only met once, but left an impression on you?

You are still the same person as five years ago, except for the places you've been, the books that you've read and the people you have met. Who has changed his outlook?

117. What do you think that you know a lot but don't actually know?

Everybody likes to believe they are experts in many things. Let's face it, most of us are average or below average at almost all things. Think about how many people will claim to be above average drivers. It is always good to reflect on yourself.

118. What are we doing to make society laughable and ridicule in 20 years?

You'll have plenty to laugh about if you look back 20 years. It will be the same 20 years later. Many things that are now popular will be ridiculed and laughed at by people. What do you think the future you will view with disdain?

119. This double standard is absurd and must be stopped.

There are many double standards available. Now it's time for him to decide if he's interested in societal issues or not.

120. Which customer service experience is the worst?

He likely has more than one. Who doesn't love a bad customer service story? He'll have plenty of customer service stories if he has worked in the field. He probably has customer service horror stories if he hasn’t.

121. What is the best way for a government control its citizens?

Ok, so I debated whether to add this one to the list. This question is more complex and important than the rest. If you don't feel it is appropriate, please throw it out. If you're both interested in history or politics, it can lead to interesting conversations.

122. What would be your top choice for a cause you'd like to dedicate your entire life to?

Each of us has causes we are passionate about. You'll now be able find out his cause. It will also tell you how active he has been in volunteering and charity. It's a great question because it allows you to compare what you are doing with your ideal life.

123. What would be your greatest achievement if you were to die today?

This is a great question to ask yourself. It is easy to lose sight of the fact that eventually we will die. It is important to remember that life is meant to be lived.

124. What can you do to make the world a better environment?

This question may have the same answer or not as question 34, but it is likely related to question 33. It's a great question that you can ask to learn about his life and what he considers important.

125. What are some people who you have only met once, but left an impression on you?

You are still the same person as five years ago, except for the places you've been, the books that you've read and the people you have met. Who has changed his outlook?

Deep Questions to Ask

126. What is the one thing you dislike about women?

127. Are you averse to the idea of dating online?

128. Do you feel intimidated by women who make more than you?

129. When you were young, who was your celebrity crush?

130. Are you afraid?

131. What do you think about me?

132. Are you a liar to get the girls you want?

133. What was the first thing you thought of when you first saw me?

134. Would you rather fall in love or win one million dollars?

135. Have any questions?

136. Which is your romantic spirit animal?

137. Who was your role model growing-up?

138. What career were you interested in as a child?

139. Have you ever been to summer camp?

140. What do you think of Sunday afternoons that are perfect?

141. Which holiday is your favourite?

142. Which is your favorite present?

143. What were your middle school friends doing for fun?

144. Have you ever had pets as a child?

145. Which childhood memory is the most happy?

146. What dish would you cook if you could make it perfect?

147. What makes you feel better when you are having a bad day?

148. What ride can you take at an amusement park?

149. What was the one toy you longed for as a child, but no one bought it for you?

150. Have you ever slept with stuffed animals?

151. Which sound do you like?

152. Which scents are your favorites?

153. Which candy are you most afraid of?

154. Which song is your favourite karaoke tune?

155. What was your favorite thing you did during recess?

160. What's your favorite thing to do when it rains?

Serious Questions to Ask a Guy

If you want to really get to know someone, it is important to ask questions. Questions help us to understand one another better and avoid misunderstandings in a relationship. The ability to ask questions helps us go from being strangers to becoming friends and then lovers. You can learn about your boyfriend's past, present, and future plans by asking questions. While asking questions can help build a relationship, not all questions will be the same. There are some questions that can destroy relationships. It is important to understand your boyfriend by asking the right questions.

You can get to know your boyfriend by asking questions. It also gives you the chance to strengthen your relationship. If you're not sure about the direction of your relationship or want to find out what he thinks of you and your relationship, there are questions you can ask. 

161. Are you still in touch with your ex?

This question is intended to discover his relationship with his Ex. It is not a good idea to be in a relationship with your boyfriend who uses you to get over him ex. You can also find out what your boyfriend thinks about being in touch with you ex to get some insight into how your relationship should look if he doesn’t like it.

162. How many years did your last relationship last, and when did it end.

It is important to know the date and length of his last relationship. This information gives you an idea of his commitment to the relationship. It also tells you how long he waited to start a new relationship.

163. How often have you been with a sexual partner?

Although you don't mean to judge, it is important to not get involved with someone who has had multiple partners. You can get a clear picture of his intentions by knowing how many partners he has had over his lifetime.

164. When were you last tested for STDs/HIV? Will you be open to another test before things get worse between us?
165. What is your opinion on domestic violence? Is there ever a reason to strike a woman?
166. How do I start my day? What do I do before it ends?

167. When was your last arrest and for what crime?
168. What are your hobbies and things you do to relax?
169. What are your best habits?
170. How can you deal with disagreements or conflicts?

171. Are you worried about our relationship?

All of us have fears about our relationships. Sometimes, it's because of past hurts and other times it is because of fear of the unknown. Knowing what your boyfriend fears about you and your relationship gives you the chance to talk it out and make arrangements for it.


172. Are you a believer in Happily Ever After?
173. What is your ideal relationship? One that leads to a marriage?
174. What would be the best word to describe your love?
175. How did you feel when you first met me.
176. How does your relationship make you happy?
177. Are you afraid of love?
178. Would you consider long-distance if something were to happen? Or do you prefer to go your separate ways?

While some people believe in long-distance relationships and will do their best to make it work, others are not so sure. It's important to know your boyfriend's thoughts on long distance relationships. This is especially important if you think it will be necessary for you to move to another area or to live in another country.


179. Tell us about one thing that you think is missing in our relationship.

This is a crucial question, especially if your boyfriend doesn't feel satisfied with your relationship. Both of you can ask and find out what is lacking in your relationship to help you both work on it and maintain your relationship.


180. What's one thing you would miss most about our relationship?

Random Questions to Ask a Guy

  1. Are you satisfied with your relationship?
  2. Have you ever considered ending your relationship with us over the years?
  3. What did you think your life would look like 10 years ago?
  4. Are you open to a career change, even if that means changing your lifestyle?
  5. Are you thinking about moving to another country or state?
  6. Is there anything that's still on your “bucket list”? It's hard to believe that you haven’t done it yet.
  7. Will you take care for me if I become very sick? Or will you send me away
  8. Are you finding me as attractive now as you did when we first met?
  9. Are you still in love with me?
  10. Will you take care of my parents if they become very ill?

Conclusion

Asking the right questions can be the difference between a deep conversation with a guy or a one off time with him. Remember, the best questions are the one that connects your heart with his heart. Never shy away from questions you feel deeply about especially if you are interested in having a relationship with a guy. Enjoy!!

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