213 Questions To Ask A Guy (Know Him Deeply, Bring Him Closely)

By Ruth Jesse

January 10, 2024   •   Fact checked by Dumb Little Man

So you are going to meet him today and don’t want to look dumb? Or is he not communicating with you more often? Either way, you want to know about the questions to ask a guy and know him better. No need to search anymore as here we are.

Then these random questions to ask him will give you a good insight into his nature and personality. Moreover, some flirty questions to ask will cherish your relation to a new level. We have picked 213 different questions to ask a guy for you.

Asking questions is definitely good. You will know him better and get a deeper look at his thoughts, mind, and personality.

We know that you are afraid about the fact that asking too many questions might give absurd vibes. You are also scared about which questions to ask and which should not. What if you say something silly or awkward?

That’s why we have picked these questions from different surveys and crafted them to be natural.

Don’t just ask them all in one go. These are applicable on different occasions as guys don’t open up about their insecurities easily. They hide their emotions and secrets well.

It’s just a myth that women are difficult to understand. Everyone is difficult to understand if they do not open up quickly.

Note: Questions in categories mentioned higher are selected from various surveys and kind of must-ask. That is why we have elaboration on every question. A few categories down the article are self-explanatory, so not every question is described in detail.

So without any further waiting, let’s begin.

❓ General Questions To Ask A Guy ❓

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These are the general questions to ask a guy either on the first date or you just met him. Even if you both get connected on social media, these questions are better. The answers may be general too, but they can create a better understanding.

You could search a few, but asking all of them will give you a good insight into his personality.

1. How do you describe yourself?

It is one of the most general questions to ask a guy when met first, and a great one to start any conversation, even on a date. It is one of the most general yet flirty questions to ask.

2. What is your nickname?

Knowing his nickname at the beginning will give you a chance to start a friendly relationship right away. You could choose this one as a question to ask a guy 1 as it will give him a vibe of comfort.

3. How are you unique?

Questions like these are worth millions of dollars on the first date or first meet-up. It is some of the best questions to ask a guy to know better from him.

4. Where had you been born?

Talking about his birth city (or country) can start a good conversation. You would at least like to know about it.

5. Have you ever get to know your best quality?

It will be better to ask about the best qualities from his mouth. See if he exaggerate or remain logical and honest.

6. What triggers you most to get rage?

It can give you info about him not doing things in the future that could make him angry. Although this is question replied friendly, it helps massively in the long run. Don’t take this as one of the flirty questions to ask.

7. How is your overall dating experience?

It is a little bit absurd question to be asked at the first meeting or date. So, better to ask after a couple of meet-ups.

8. Do you visit your parents often?

A question about his family is among the good questions to ask a guy to get to know him better. See how much he cares for family values.

9. Would you like to tell me about your family?

This question will tell you more about his family. Please don’t talk to him on this topic longer on your first date, as he would like to know about you too. Not there to tell you about his family tree.

10. What is the goal that motivates you?

This question will describe his passions and life goals. What excites him? He will tell you about his dream job or what he will prefer more.

11. What are your ambitions?

Somewhat the same question but still with different answers. Maybe he will tell you something different about his goals, about his bucket list. Just don’t ask him at once.

12. Who is your favorite personality?

In the initial talk, it is one of the good questions to ask a guy. 1 He will tell you about the personality. 2 He may be more likely to give a funny answer.

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13. What is the best achievement in your life?

Questions about his achievements are great to make him feel good. They will create delightful connections.

14. Do you think you are an introvert or extrovert?

This general question will help you to know about his nature on the first date. Either he is the life of the party or just a party popper.

15. How religious are you?

If you prefer religious ones, then asking this question will help you to get to know his religious preference.

16. How are your relations with your friends?

Asking a guy about his friends’ relations is good to know about his social activeness. This question will also build a base for your extrovert/introvert question.

17. Do you think guys and girls could be best friends?

It is among some general questions to ask a guy. Most of them are not open to these kinds of relations. It is good to know about it at the start.

18. Which qualities would you want to see in your life partner?

It is one of the most favorite girls’ questions to ask a guy they had a crush on. And it is not a wrong question to ask on a date too.

19. How was your childhood?

It is fun to ask something like that. Guys mostly come up with any colorful childhood memory to talk about. Cute questions are sometimes more important than the flirty questions to ask.

20. How will you describe yourself in one word?

It is a short question to ask a guy if you want to test his selection of words. How he describes himself is a sign of how you could strengthen your relations with him.

21. Do you like winter or summer more?

Talking about weather and likeliness towards a particular season is something even a stranger would discuss. Why won’t you?

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💞 Questions To Ask A Guy For More Intense Connection 💞

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Asking questions like these will make a more intense connection between you two. Some of these are asked on a date, while others can ask a guy you like. Let’s have a look at these questions.

22. How do you feel around me?

For a guy, questions like these will trigger a strong connection towards the asking girl. It can spice up the conversation too. It surely is one of the straightforward flirty questions to ask.

23. Do I make you nervous?

After asking this question, you will control the conversation (even if you are nervous too). It can also ease up both of you.

24. Would you rather choose a love marriage or arranged one?

A question like this one will give you an idea about his thoughts towards love. We have more detailed questions about it down the article. So sit back because there are still 189 to come.

25. What is your number one priority?

It will be an excellent question to ask as he might tell you something that you can help with. If you can help, then he will be more attracted.

26. Which of your trait do you hate most?

Asking something like this is allowing you to analyze himself. It will be helpful for you to build a closer connection by not provoking that trait.

27. Would you confess your love at first sight or wait till the right time?

Ask a guy something like this will also create an intense connection. It is one of some random questions to ask a guy yet allows you to get deeper into his comfort zone. It is one of the cutest flirty questions to ask.

28. What do you like about me?

Now, this is an intense question to ask a guy for stronger connections. He may tell you about your personality or any trait which he likes most. Pay attention!

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29. Do you believe in love at first sight?

If yes, then there is a chance he might have felt something towards you too. And believe me, most of them answer this question as yes.

30. Would you search for your girl or let fate bring her to you?

His answer will tell you a lot about his intentions to find a mate. Either he is looking for someone or just waiting for the right time.

31. How do you imagine your dream girl?

Asking about his ideal girl will create an intense connection between you two. It will open up a more personal portal for him.

32. How do you start a conversation with a girl?

The answer might be interesting as he will tell how he could approach you. It would be better if you don

33. What is the first thing that you notice in a girl?

It is also among intense questions to ask a guy, as he will look at you again in a different way. He will search for traits about you that appeal to him most.

34. What is your idea for love?

It can be a thoughtful question to ask a guy. If he’s deep, you might get an emotional definition. Or he’s a funny one, you laugh.

35. What do you expect from a love relationship?

And you got the best intense question for the guy you like most. It will give you a chance to do stuff that he had expected.

36. Do you believe that love can happen multiple times?

Another thoughtful but intense question for a guy and the answers may be different from different personalities.

37. How can a woman gain your trust?

It will be a million dollars question to ask your guy. He will describe what he likes most so you can do those things.

38. What is your biggest regret?

When a guy tells someone about his biggest regret, it means she is too close to him. Try your luck to be that particular person and get closer to him.

39. Have you ever dated someone your family relative?

If a guy tells you about him dating a mother’s friend or sister’s classmate, it means he feels comfortable around you.

40. What was the one time when you stepped out of your comfort zone?

Guys don’t tell much about their comfort zones. So feel free to ask it, as it may bring him closer to you.

41. How would you introduce someone stranger to me?

In explaining so, he might tell you things that you haven’t noticed, but he likes about you as a partner/friend.

💣 Questions To Get A Guy’s Full Attention 💣

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These are some questions to ask a guy to get his full attention towards you. No matter what he is doing, he will stop for a moment and look at you.

And it also has some questions about things of your guy’s interests. Guys love talking about what they love most, their passion, and the exciting time of their lives.

This category includes some surprise questions too. So let’s take grab his full attention.

42. Did you have a girlfriend in the past?

It is a girl’s most favorite surprise question to ask her guy. It doesn’t matter if he says ‘yes’ or ‘no,’ but for a second, he will be stunned.

43. In your life, what would you want to achieve more?

Talking about his interest will be great to get closer to him. He would love to tell you more and more about it.

44. What are some other side goals of your life?

It will help you to get to know him better and his side goals. There should be more on his bucket list; you maybe want to know.

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45. Have you ever kissed someone?

46. How old were you when you had your first kiss?

47. How was your first kiss experience?

For a guy, questions like these three mentioned above will make him divert all of his attention towards the speaker. You will make him go to memories years ago.

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48. Rate your last relationship on a scale of 0 to 10?

It is not a risky question to ask. If he had any, he would rate it. Even if he doesn’t, then you have gotten his attention and know about his simplicity. Though it is flirty questions to ask but it will make him think deep.

49. Tell me a story about your wildest adventure?

People encounter various moments that they enjoy the most. Definitely, your guy has experienced it too, and he might get excited to tell you all about it.

50. One thing that is the most embarrassing in your life?

The majority of the most embarrassing moments are funny to talk about later. It will create a stronger bond between you two when a bit of some personal experiences are shared.

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51. What would you do on your first date?

There is no doubt he has some imagination about how his first date will happen, what he will do? Asking such questions will help you to know his romantic side better.

52. In your life, what would be your ideal wedding like?

He will love to tell about his ideal wedding plans, gaining his interest and attention. Since you are getting your hands on the flirty questions to ask, this one would be ideal.

53. What do you prefer, love or friends with benefits?

Questions like these are also potential to gain the full attention of your guy. He might answer the love part casually, but look you at words friends with benefits.

54. Do you believe in ghosts?

It is an interesting question as well as can grab the attention of guys when asked from nowhere. And it will help you to understand his belief in paranormal activities. Maybe he’ll think about this question later.

55. Have you ever encountered a paranormal activity?

It can be asked if he replies ‘yes’ to the above question. The conversation will be great.

56. What’s the worst injury you ever had?

Although it is a sad question to ask, some funnily tell their worst incident. Ask it if you think he will tell you a great story instead, hence gaining his attention and knowing him better.

57. Would you rather spend on fashion or food?

It is also among some good questions to ask a guy to know about his preferences.

58. Have you ever been addicted to anything?

Talking about this topic will make him perplexed. And he might tell you the truth; replies are often no.

59. What are you too old for but still enjoy?

Again a question about his interest that he will love to talk about.

60. What’s the most meaningful gift you’ve ever gotten?

People sometimes receive gifts that are so helpful to be the best. Did your guy has gotten something like that?

61. How do you deal with people you don’t like?

It is also a surprising question. As it is uncommon, he will convert all of his attention towards you to answer this question.

🤣 Funny Questions To Cherish The Mood 🤣

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These are some random questions to ask a guy with a slightly fun element in them. These questions are fun to ask and fun to answer. They will cherish the mood and build a stronger bonding between you two.

Some of them are not explained as they are self-explanatory. To a guy, questions like these will show them how good your sense of humor is? Also, here’s included some fun questions to ask a guy that will result in an interesting story.

So, let’s have a look at these.

62. Would you love to smoke a joint if it becomes legal?

63. Have you ever been pranked by someone?

Everyone gets pranked; probably he had been too. He will be amused to describe the story.

64. Have you ever prank-called someone?

Been pranked and prank someone, you know both are different, and probably he had experienced both. So ask this one too.

65. Did you ever have a crush on your teacher?

It is also a fun question to ask. Maybe in this world, his first crush might be his teacher. These things from school time, years ago, are never forgotten.

66. Have you ever fall in love with a movie character?

67. When was the last time you were stoned?

68. Can you think of movies without a script?

69. If someone wants to know about your sense of humor, what joke would you tell them?

And he got a chance to make you laugh, so brilliant one divert the conversation to something interesting.

70. Are you made of Copper and Tellurium? (’cause you are CuTe)

Mostly, guys ask this pickup line, but there’s nothing wrong if you said it.

71. Name someone with whom you would most likely get stuck in an elevator?

72. Have you ever teased your siblings till they get mad?

73. Do you enjoy eating free food?

74. Who would you haunt if you were a ghost?

It is among the best fun questions to ask. He would love to tell you about it.

75. What is one story you tell that always makes people laugh?

76. What always makes you feel like a little kid?

77. What was fun to do once, but you’ll never do it again?

78. If you wake up as a girl one day, what will be the first thing that you do?

Now this question will be great to make your conversation a funny gender-biased war.

79. Which came first, the egg or the chicken?

80. What’s your biggest kitchen failure?

81. Has anyone ever walked in on you naked?

It is a bit personal, so don’t ask it on the first date. It is suitable when you both have proceeded.

82. What is your craziest dream?

Everyone has absurd dreams that never make any sense. He must have that crazy one in his memory and would love to share it.

🔅 Questions To Make A Match 🔅

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These are some questions to ask a guy to see which things both of you have in common and different? And these questions also include what about him is perfect for making a match with you. They are actually fun questions to ask a guy, but a separate category will cover them better.

You don’t have to ask them all; ask what you desire.

83. What is your favorite movie?

84. What genre of movies do you like?

Everyone has a favorite movie, which is considered perfect in the world. Also, there is always a genre people love to watch. Ask him his and share yours.

85. What is the number one cuisine you have ever tried?

86. Who is your favorite actor/actress?

87. Who is your celebrity crush?

Now don’t be afraid and jealous to ask about his celebrity crush. She might be someone whose acting both of you like. And there is nothing wrong to fall in love with a celebrity, right?

88. Who do you think is the best singer in this world?

89. Which type of music do you like the most?

90. What are the top ten songs on your list?

What brings two people closer is music. If they had a shared taste in music, they could remain together for longer, and the connection between them is more substantial.

The questions to ask a guy about which song, singer, or music do you like to hear are great. It will be better that you two have the same genre of music taste and what could be more than best if both of you have almost the same top tens list.

91. Do you watch anime?

92. Who is your most favorite anime character?

93. What is your favorite pet?

94. What is your hobby?

Asking about his hobby is among the must-ask questions if you want to get to know him deeper. Either the hobbies themselves match, or both of you are north and south poles that attract.

95. What is your favorite color? Why?

Asking a favorite color is a general question, and guys can’t usually describe why. But if you insist, then he might tell you reasons that could help you understand him closely.

96. What is your favorite food to eat when you are sad?

97. What makes you smile, no matter what happens in this world?

This question will tell you did he also pleases on things that please you. It has a romantic element too.

98. Would you ever lie to someone you love?

And remember, you are most likely to get the answers like ‘It depends.’ But eventually, the guy will tell you what his honest answer is and why.

99. Would you like to change anything about yourself?

100. What is your favorite destination for your honeymoon?

If you are in a relationship, it is one of the perfect questions to ask a guy. Do both of you think about the same honeymoon destination?

101. Do you lead your life with your heart or your head?

102. What is one thing a woman can do that would instantly turn you off?

It will help you to be cautious about things that can turn his mode off. Also, he maybe curious to know about yours. In the end, both of you will understand what not to do that will displease the other.

103. One thing you like about me?

A conversation about what both of you like in each other is a giant leap towards a strong relationship.

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🥂 Romantic Questions To Ask A Guy 🥂

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These are some romantic and flirty questions to ask a guy to make a stronger bond with him.

A guy likes when his girl asks romantic questions too. Ask a guy flirty and romantic questions like these and enhance your relationship bonds.

104. What is that one temptation you can never resist?

For a guy, questions about his temptations touch his pleasure instincts.

What in the world he cannot resist is good for you to know.

105. What is your greatest guilty pleasure?

It is too flirty to ask a guy. Would you rather take the step or let it go?

106. What’s your go-to flirting move?

107. What is your best pick line so far?

Ask a guy flirty question like this one, and he will do his best to impress you.

108. Would you think of dating someone older than you?

109. What would you say is your idea of romance?

Ask a guy questions like these ones to get familiar with what he can think of romance.

110. What part of the female body are you most attracted to?

Ask this question in light mode, as it has a kinky flavor in it.

111. What are your thoughts about the world celebrating Valentine’s Day?

Every lover in this world thinks Valentine’s Day is special.

You can also think about how he will make this day great for you by this question.

112. Do you think that there is a special reason why we met?

113. Is there a song that reminds you of me when you’re listening to it?

114. Do you have a pet name for me?

115. How do you feel when I send you a text message?

Ask a guy flirty question like this, and next time you will definitely smile about the results.

116. What outfits do you like the most on me?

117. Would you carry me in your arms if my feet hurt?

Now, this is truly romantic. Ask a guy flirty and intensely romantic questions as such to take your relationship to a higher level.

💠 Personal Questions For A Guy 💠

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Warning: These are the questions to ask a guy if you are together for a long time. They cannot be asked if the relationship is newly built and both of you haven’t covered the likes and dislikes stage.

These questions could target the insecurities of a guy, or something too personal, or about anything he hates.

If asked at the wrong time, these questions would upset him and could affect your relationship.

But if answered properly, these questions will make you know your guy deeper and more closely. They will open a more personal door for you towards him.

So, ask them according to the situation and the complexity of your connections with him.

118. What will be your first step when faced with a conflict?

119. Who is the first person with whom you share your disputes?

120. Who is the most important to you in this world?

121. Have you lost someone close to you?

These four questions will open him up to tell the person he cares about most.

122. Which personality trait do you see in others and wish you have?

123. How much is your salary?

124. How do you deal with failure?

Both of these questions can drive insecurity in a guy. Be cautious while you say the words.

125. Would you share any significant childhood memory that has played a role in your development?

126. Have you harmed yourself over something?

127. What’s your worst family memory?

128. What is something you would never spend money on?

129. What are you most afraid of in this world?

A couple of them might sound general. You can think about what’s wrong with these, but to a guy, questions like these may not be so general.

These questions could be too personal for him to share. Or they could remind him of a terrible memory.

When asked at the wrong time, these can upset him about something.

130. How many people have you seriously dated?

131. Have you ever done drugs?

132. Have you ever been physical?

These are seriously too personal questions to ask a guy. Ask him if you are close enough to him, as these questions will make you his best friend and secret keeper.

If he tells you what he has ever done from any of these, then think you are the special and really close person in his life.

133. Are you comfortable telling me your weaknesses?

Answer to this in the form of weaknesses means he trusts you enough to tell you.

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134. What’s a bad movie that you love even though you know it’s terrible?

If there is a movie that people criticize much but a guy likes it, he would feel shame talking about his likeness. By asking this question, you will get closer to him if he tells you.

135. What’s your definition of a healthy relationship?

136. Do you think your zodiac sign is accurate for you?

137. Would you rather travel with friends or a significant other?

138. What is something you think everyone should experience at least once in their life?

139. Is there a song that always brings up old memories for you?

140. What is something you know you are judgmental about?

These may seem like some trivial random questions to ask a guy, but they have different personal opinions about them. They usually don’t answer these questions seriously, but you will get a deeper look into him if he tells you.

141. What’s your biggest phobia?

Guys are shy to talk about their phobias, so they don’t open up quickly to tell them. Only their therapist knows or those who are personally close.

If you think you have reached that stage, then ask to become that one particular person.

142. How many kids would you like to have in the future?

If you are not his better half, fiancé, or girlfriend, then stay away from this question to ask. If you don’t have reached the stage, then questions like these will give other meanings to a guy. It is way too personal.

👐 Interesting Questions To Ask A Guy 👐

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Here is also a list of questions to ask a guy, which are exciting and creates a colorful relationship. As these are self-explanatory, so they are not described in detail.

You will have fun asking them to a guy. He would think and answer something silly to make you laugh too.

With these questions, the conversation will be so interesting. Hence making your relationship deeper.

143. Which music do you like to listen to while traveling?

144. What is your favorite shop to store at?

145. What is your favorite fashion trend right now?

146. What is the one thing that you are really good at cooking?

147. How do you get to know when a girl is interested in you?

148. What is your least favorite food?

149. What is the one piece of advice you would give to your younger siblings?

150. Do you work out more often?

151. Have you ever been dieting?

152. If you are a superhero, which superpower would you like to have?

153. What is your bucket list?

154. Which holiday do you like the most?

155. Would you rather game or play physical sport?

156. What is your favorite scent?

157. Who would you choose to play you in a movie about your life?

158. Would you rather have the power to be invisible or to read minds?

159. What did you think was silly until you tried it?

160. What’s your favorite reality show?

161. If you could travel back in time, which moment would you love to relive?

162. What is something illegal that you think should be legal?

163. What is one thing you will never get bored of for the rest of your life?

164. What is your dream job?

165. What would you do if you win a hundred million dollars?

166. If you could learn one skill right now, what would it be?

167. Do you have a favorite car? Which one is it?

📴 Dirty Questions To Ask A Guy 📴

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If you want something kinky and spice up your relationship to the next level, then these questions to ask a guy will be best.

For a guy, questions like these are a big turn-on.

Warning: If you are not close enough to him, he won’t answer. Instead, take them as something else. You will be portrait as any lust slave.

168. Have you slept naked?

169. Have you had a wet dream?

170. How are you in bed?

171. Do you like to role-play?

172. Have you watched any blue films?

173. Have you ever made out with someone?

174. What’s your favorite sexual fantasy?

175. What is your favorite place to be massaged?

176. Do you like it when someone pulls your hair?

177. Do you like it when the girl makes the first move?

178. Do you like cuddling?

179. Have you ever played dirty truth or dare?

180. What is your favorite thing to do to me?

181. How do you feel when I touch you?

182. What have you always imagined doing with a girlfriend that you’ve never done?

183. When you’re alone, do you ever imagine that I am there next to you?

❔ Questions Girls Are Afraid To Ask Guys ❔

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Below is a list of questions to ask a guy that are girls afraid of. These have the potential to upset him, or he may not be comfortable answering.

These questions are usually not advised, but they might enhance your relationship status if asked appropriately.

Because they are just situation sensitive, it doesn’t mean they shouldn’t be asked.

184. Which trait do you consider an imperfection in women? Do you see that in me?

185. How do you feel if I earn more income than you?

186. If you could change anything in me, what would that be?

187. Would you choose to cheat on me for someone rich?

188. When are you gonna propose to me?

189. Would you let me check your phone?

190. Do you mind if I have male friends?

191. What is something you don’t like about me?

These questions have the potential that you may be given answers that you won’t like to hear. So be cautious before asking them.

192. How do you feel about (any of your friends)?

193. Why did you break up with your ex?

194. Would you rather choose, Career or Family?

Girls are afraid of these questions to ask as they may upset him.

195. Have any of my qualities reminds you of someone else?

196. Do you think you are the person you have dreamt of?

197. Do you still miss someone you have loved in the past?

198. Do you often get compliments from females?

As these questions may trigger his insecurities, girls are afraid to ask them. And for these questions, they are right not to ask.

🚫 Never Ask These Questions 🚫

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Photo credit: Pexels.com

Last but not least, you should never ask these questions. Above are the hesitant questions to ask a guy, but the following are a big NO.

All of them are about severe insecurities or those to which they will always lie. So, avoid these questions to ask a guy.

199. What is your worst quality?

200. Do you believe your friends describe you negatively?

201. How do you compare yourself with (name of any age fellow)?

202. Do you think (name of a person) is more successful than you?

203. How do you manage your job earnings?

204. Have you ever cheated?

205. What are your measurements?

206. What does your family think about me?

207. How was your last relationship ended?

208. What is the one thing that you will regret for the rest of your life?

209. Would you tell me your social media accounts’ passwords?

210. Are you jealous of one of my male friends?

211. What is the name of your ex?

212. Are you rich?

213. Who is more important to you, your family or Me?


Photo by Cam Ferland on Unsplash
Photo credit: unsplash.com

You have an ultimate list of 213 questions to ask a guy. All of these questions are selected by various surveys and real-life scenarios.

You don’t have to ask all of them. Just pick those according to the situation and personality of your partner. Ask the critical ones at the right time.

These will not only help you to strengthen your relationship but also make you know him better.

For more tips or questions about how to deeply know him, WATCH THIS VIDEO!

Ruth Jesse

Ruth is a life coach who specialises in relationships and career development. Outside work, she loves writing novels and guides for personal development.

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