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21 Questions to Ask a Guy to Start a Conversation

Great questions to ask a guy to deepen your relationship or help you start a conversation. These questions will help you to get to know him better especially if you are just starting out.      


It is not always the easiest to get to know what your guy is thinking, in fact it can seem impossible at times.


 Asking questions in a game form can help you get the answers that you may really want without having it feel like an inquisition.


What is the game 21 questions?


Just choose 21 questions to ask each other that will help you get to know them better.  First think about what you really would like to find out the answers to. 


You can ask questions about their past, how they feel  right now or what they imagine their future to look like.


 If you are just getting to know him, you may want to ask your “deal breaker questions” in a creative way. 


If you are married you may want to ask questions to see if you are on the same page for your future.


What was an embarrassing moment that you remember- random questions to ask a guy


21 questions to ask a guy


Choose the questions that fit your relationship. Some are for the beginning of the relationship and others are more appropriate for a more committed one.


 Some may just inspire you to create your own. Obviously only you know your deal breakers if that is something that you would like to ask about.


We have more than 21 one questions listed, but you can pick and choose and use them for more than one game night.


What should I say to my crush?


Give an honest compliment. Pick out something about their appearance or their personality and let them know what you like about them.


 Some questions to ask your crush when playing “21 questions to ask a guy” are listed below.


What do you find attractive in women?


Tell me a secret that you have


What are you passionate about?


Do you have a crush on anyone?


What are your ideas for a fun date night?


What was the most exotic food that you have ever eaten?


What is the most adventurous thing that you have ever done?


Where is a place that you would love to visit?


what do you find attractive in women- fun questions to ask a guy


What are some random questions to ask?


What is your favorite comic book character?


What talent do you have that is not obvious?


What is your favorite music genre?


What was one of your favorite vacations?


What conspiracy theory do you believe?


If you could, would you go into space?


What is a movie that you like that I would never guess?


What is your favorite show or movie series to binge watch?


What scares you?


What does your dream house look like?


What time period appeals to you most?


Who do you admire either personally or professionally?


What concert would you love to see?


What was your favorite concert that you have gone to?


What was the funniest movie that you have ever seen?


What drives you crazy?


What do you think future generations will think of our moment in time?


What things in life do you find completely unfair?


What was an embarrassing moment that you remember?


Are you a cat or a dog person?



What was an embarrassing moment that you remember- funny questions for guys


What are personal questions?


What is something on your bucket list?


What charity/charities do you like to support?


What is your worst trait?


How long was your longest relationship?


What is the worst thing that you have ever done?


What is a goal that you have for your life?


Who do you admire?And  why?


Are you spiritual or more traditionally religious? Or are you a non believer?


How do you feel about politics? Who do you support?


What values do you feel strongly about?


Did your parents have a good relationship?


Are you close with your parents? Who are you closer with?


What is the happiest memory that you have as a child?


Did anything traumatic happen to you? Do you think it changed you?


Are you competitive? 


tell me a secret that you have -deep questions to ask a guy


What are some deep questions?


Are you environmentally conscious?


If money were no object what would your life look like?


When was the last time that you were really happy?


How do you see gender roles? 


Who should take care of the house when a couple lives together?


Who should be the main child caregiver? If you want and see children in your future.


How should a couple deal with everyday finances and big money issues?


What does your life look like in 5 and 10 years?


What reasons do you think are valid for getting a divorce?


What were some of the problems in your last relationship? What did you learn from your past relationships?


What was your biggest failure?


What were your greatest lessons from that failure?


Do you trust people in general?


random questions to ask- What was an embarrassing moment that you remember_


What are some questions to ask a guy to start a conversation?


First thing is to find anything in common as a starting point. If there is something interesting about the place that you are or the place where you met, mention that. 


If you have a friend in common, then start there. Another great way to start a conversation is to ask a question. The easiest question to ask someone is about the location of something. 


  1. Do you know where the closest Starbucks is located? 
  2. Is there a good Ice cream shop that is close by?
  3. I am looking for the nearest bank, do you know what banks are nearby?


After you ask the initial “location” question. Give an honest compliment such as


  1. I just wanted to say that I love the cologne/perfume that you are wearing.
  2. That color looks really nice on you. 
  3. You really have a kind smile.


The idea is to pay attention to anything that stands out about them. That could be something that they are wearing or something about their appearance.


 This is a very easy way to start a conversation with a guy. There is nothing that is stressful about asking directions and giving someone a compliment plus it will make you both smile and feel good.


End this short encounter with a smile. Then let him take it from there. Give him the opportunity to take the conversation further!


Questions to ask a guy to start a conversation after meeting


Once you have been introduced, then the questions should be a little bit more probing.


  1. Have you worked on anything interesting or exciting lately?
  2. Have you been to this (restaurant, event, conference ) before?
  3. I was going to order an appetizer or drink. Do you recommend anything really good from this place?
  4. How do you know the host? (or another common friend that is also there)
  5. Have you seen the latest series on Netflix? What did you think?


130+ Ice breaker Questions & Texts to have Amazing Conversations

How to Start a Conversation Over Text (that Can’t be Ignored)


tell me a secret that you have- deep questions to ask a guy


How do you make a conversation interesting with a guy?


Check out our tips that in our posts listed below for great conversations. 


 Being a great conversationalist really boils down to listening and asking questions. People love to talk about themselves so if you let them they will notice!


Keep  conversations moving along by asking a question about things that they have mentioned before. 


Add your own experiences to the conversation to show that you understand and have had some similar things happen to you.


 Having things in common will create the start of a bond. You want to be trusted so that he will feel comfortable in opening up to you.  


How to have interesting conversations in any situation



Conclusion 21 Questions to Ask a Guy


We have over 500 questions in posts below for you to use on date nights or whenever you want to have an interesting conversations. 


It isn’t always easy to just jump into these conversations, this is why questions make that so much easier. 


You could add questions to each of your date nights to make sure that you have a deeper conversation and  feel a little more connected.


Life is busy and chaotic, but it only takes a moment to reconnect!


125+ “How Well Do You Know Me?” Questions for Couples

What are the Best Date Night Questions?

Funny “Would you Rather Questions” to ask Couples and Friends

73 First Date Questions That lead to Insightful Conversations

175 Fun Questions to Ask to Get to Know Someone

36 Questions to Fall in Love





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