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Topics that Get to The Heart of What He REALLY Thinks

Our “things to talk about with a guy” conversation topics will get to the heart of his real or hidden thoughts. While asking  fun, flirty & deep questions are perfect to get to know him better,   

it’s the stories behind the answers that will truly reveal his underlying feelings. 


When you find out the story of “why he answers a certain way,” you will find his true personality

shine through. These are great to use for your boyfriend or crush, In real life or over text.


Things to talk about with a guy


You will never have to look for things to talk about with a guy, we have you covered!


Everyone hopefully has grown from who they were when they were younger to who they are today. We each have our own quirks and opinions.


The goal is to get to know him for who he really is today. To do that you need to really listen to his answers.


Let’s take a simple example. If you ask the question,


topics to talk about with a guy


Would you ever consider being a vegetarian? If his answer is, No Way! People that don’t eat meat are crazy. Well that tells you that he may see things in a more black and white way because he feels negative towards the people that don’t eat meat.


If he answers that he would like to cut back on meat because so many athletes that he admires are vegetarians. That answer is more thoughtful and he sees the health benefits. This answer can open up a further discussion of health and how important it is to him.


Who he is can be found in the stories that he tells about “why” he answers the way he does. We are all complicated so until you know him better, try not to make rash judgements. 


Always follow up on anything that makes you question his view on something. Asking questions allows you to get a lot of information in a relatively quick way. 


We are going to split up the topics into when you first meet a guy, and things to talk about with a guy to get to know him better.


Things to talk about when you first meet


This will be dependent upon where and how you are meeting. Pick up on anything that has relevance to your surroundings.


Remember these important tips to get attention


  • Smile and hold eye contact
  • Look away and look back, hold eye contact for a few more seconds
  • Change your proximity, find a way to get closer
  • Then ask a question 


  1. Do you know_____ well? This is if you are at a friend’s gathering in which you can ask how he knows the host.


  1. Can I ask you what you are drinking? That looks interesting…


        This is if you randomly see someone at the bar or table and you would like to start a conversation with them. You can just say after..sorry to bother you, thanks!           And smile.


  1. Or you guys look like you are having fun! Then the ball is back in their court. If they follow up, you can continue the conversation, if not.. Then nothing was lost!


  1. Do you know where the closest bathroom, coffee shop, bus/subway stop is? You get the idea, if you are on the sidewalk, or in a cafe…just ask a simple question and smile.

         (a smile goes a long way in showing intention!)


  1. Have you ever tried their ___________? I was thinking about getting it, but don’t know if it’s good. This is if you see someone in a bakery, bar or restaurant.


  1. Have you been waiting long? This is for when you are standing in line somewhere…


  1. Are you waiting or meeting someone? This is for when you are out and see someone that is solo


topics for conversations



Once you have started the conversation, then you can move onto

Getting to know the basics 


  1. Ask his name and if he’s single 


  1. Do you live in this area/city?


  1. What do you do for work? Do you enjoy it?


  1. Ask about something that has made news that day or a recent sporting event.


  1. Finally, if you enjoyed meeting him and talking, then tell him so. This will give him the green light to ask you out or you can also ask if he has any plans for the following weekend!


Once you get past the small talk or you already know him a bit, then these topics will allow you to get to know him better. Just remember to follow up, ask “why” and listen to his answers. They will tell you a lot!


Things to talk about with a guy to get to know him better




13.What do you enjoy doing in your free time? 


  1. What sports do you play or enjoy watching


  1. Do you have anything fun planned for this summer/spring/fall/winter?


  1. Do you enjoy traveling? 


  1. What places have you visited that you really enjoyed?


  1. What activities really make you happy?


  1. Do you have any hobbies?




  1. Do you enjoy your career?


  1. Do you see yourself doing the same career in the future?


  1. If you could start over, would you be doing anything else?


  1. Have you ever wanted to start your own business?


  1. How well do you usually get along with your coworkers?




  1. Do you have siblings that you are close to?


  1. Who do you talk to more, your mom or dad?


  1. How often do you see or talk to them?


  1. Do you celebrate your holidays with them?


  1. What do you miss about being at home?




  1. Do you want children? 


  1. What are you kids like? (if he or you have kids)


  1. Do you ever want to move to a different location/state or country?


  1. What does retiring look like to you?




  1. What things are on your bucket list?


  1. What does it mean to be successful to you?


  1. How has the pandemic changed you?


  1. What do you want your life to look like in 10 years?


  1. Do you make goals for yourself?


  1. What are you most proud of that you have achieved?


  1. What dreams do you have for your life?


  1. Do you think that you are an ambitious person?


Relationship things to talk about


  1. Have you had many long term relationships?


  1. Have you ever been married/engaged?


  1. How long was your longest relationship?


  1. What do you think the biggest problems were in those relationships?


  1. What do you consider deal breakers in a relationship?


  1. Could you ever forgive someone that cheated on you?


  1. Have you ever cheated on anyone?


Social media


  1. Where do you spend the most time online?


  1. How long can you go without looking at your phone?


  1. Does it bother you when people are texting when you are together?


  1. Have you ever made “phone rules” when you were in a relationship with someone?


  1. Do you post personal updates online? Where and how often?


how to keep a conversation going over text




  1. Where do you get your news from?


  1. Have you changed your opinion about something recently?


  1. What are your thoughts on vaccines?


  1. What are your thoughts on climate science?


  1. Have you ever experienced a racist environment?


  1. How strong are your opinions? 


  1. Do you research things you are unsure of online? Where?


  1. Do you trust science?




  1. What have you watched lately that was really good?


  1. How often do you binge watch shows?


  1. What genres of movies do you like the most?


  1. Name a few of your favorites.




  1. Ok, the weekend is here..What are your favorite activities to do? 


  1. Do you like to celebrate the seasons? How?


  1. Would your first choice be to watch a movie or go out on a weekend night?


  1. Are you more of a home body or adventurer?


  1. Do you like to plan things or are you more spontaneous?


Food things to talk about


  1. What desserts or sweets do you like the most?


  1. Which family dishes do you get cravings for?


  1. Are there any foods that you don’t like?


  1. What snacks do you always have handy?


  1. What is your favorite comfort food?


  1. How far would you go for a favorite food?


  1. Would you ever plan a vacation around food?




  1. Do you listen to new music or mostly older bands?


  1. Do you like rock, hip hop, r&b, dance, classic or country?


  1. What is on your playlist right now?


  1. Are you looking forward to seeing any upcoming concerts?


  1. Do you enjoy seeing live music at bars or restaurants?


Health & fitness


  1. How often do you like to work out?


  1. What is your favorite way to get exercise?


  1. Do you pay attention to your diet? What do you like to eat?


  1. How often do you have a cocktail or drink?


  1. Did you ever switch the way you were eating for health reasons?




  1. Do you like animals?


  1. What pets do you have now?


  1. Dog or cat person?




  1. Who are your closest friends?


  1. How often do you talk to them?


  1. What was the craziest thing that you have done together?


  1. What do you normally do when you get together?




  1. Do you like reading books? 


  1. What was the last one that you enjoyed?


  1. What podcasts have you listened to?


School or college things to talk about


  1. What did you study in school?


  1. Would you ever want to go back and get a higher degree?


  1. Do you like to learn?


  1. What did you enjoy the most in school?


  1. Do you keep in touch with any college friends?




  1. Do we make our own success or is it a rigged system or a little bit of both?


  1. What qualities are the most important to you in a partner?


  1. What are your strongest personality traits?


  1. Have you ever taken a personality quiz? What did you learn about yourself?


  1. What is your worst trait?


  1. Can someone persuade you to see things in a different light?


  1. How would your best friends describe your personality?


  1. Do you think that you have integrity?


  1. How would you describe your sense of humor?


how to have a conversation over text


Childhood things to talk about with a guy


  1. What do you remember the most from your childhood?


  1. Do you have fun memories?


  1. What kind of kid were you?


  1. How have you changed the most from when you were young?




When you want to dive into deeper conversations, then you need to find out his views on religion or spirituality. 


  1. Do you practice a religion?


  1. How strongly does your religion color your views?


  1. What do you think when a person calls themselves “spiritual?”


  1. Do you believe in God?




Talking about religion or politics are necessary when you are trying to find out if you are a match. They are deeper conversation topics that require listening. Try to not rush to judgement or get personal if you really want to find out the answers. 


Studies show that people only change their opinions through empathy if at all. So never think that you can change someone’s mind, it’s complicated and very entangled with a person’s identity.


  1. Do you belong to a political party?


  1. How often do you vote?


  1. Have you ever been to a protest?


  1. How do you feel about our country’s gun laws?


  1. How much does politics matter to you?


  1. What do you think of the opposite party?


120 Questions to Ask a Guy Over Text


How do I keep a conversation going with a guy?


  1. Keep a list of questions handy
  2. Ask “Why?”
  3. Follow up! Use his answers as a jumping off point to other questions or conversations.
  4. If the conversation comes to its natural end, don’t panic! Continue with “I enjoyed our chat and would like to get to know you better” or/and “Would you like to grab a coffee or a drink this week?”


21 Questions to Ask a Guy to Start a Conversation


What are topics to talk about with a guy? 


We have literally around 1000 questions to ask that make your conversations insightful! 


We have lots of specific questions but the topics are whatever you normally enjoy talking about. Most people like to talk about themselves, so ask about their past, present and future plans.


101 Interesting Questions to Ask for Engaging Conversations


How do you keep a conversation going with a guy over text?


Use our “hooks” from this article. We have simple ways to also pique his interest so that he keeps texting you! 


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


things to talk about with a guy


Conclusion things to talk about with guy


When you need interesting things to talk about with a guy, turning questions into a game is the only way to go! Add these questions to your date night or over text to get to know him better. 


The longer couples have been together, the easier it is to fall into unhealthy patterns of communication. It’s so important to brush up on these skills to make sure that we don’t shut down our most effective way to connect with each other.


 Disagreements often come from unmet expectations, but it’s on us to make those expectations known. We have to communicate effectively and also listen effectively.


Making relationships grow and remain strong through communication is one of our top goals at Rendezvousmag.


 We would love to hear about things that you have tried that have made a difference in your own relationships. Cheers! Kim


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