Conversation is underrated. Most people don’t realize that asking questions is the lifeblood of a good conversation. Ask boring or yes or no questions and conversation dies quick. Open him up and he’ll talk to you. Ask good questions and he will love talking to you because it requires no effort for him to keep opening up.
Communication and conversation is one of the pillars of attraction.
The better a guy feels listened to, understood, curious about you, and emotionally invested in your conversation, the better he will enjoy speaking to you.
What you don’t want to do is drill him with questions. But if you ask the right ones and help him feel at ease, you can get him to want to keep talking to you.
Here are 25 questions you can ask a guy that will keep him interested, emotionally connected, and wanting to talk to you more.
25 Things to Ask a Guy to Keep the Conversation Going
1. What do you usually like to do when you have free time?
Questions like these are great for opening him up to talk about whatever he wants because it’s centered around him. It can tell you about his hobbies, passions, interests, and lifestyle.
This question alone can open up an entirely new direction for the conversation.
People love talking about themselves. Opening up about what they love does two things: it reveals information about him, and it allows him to open up to you naturally.
Read also: 205 Weird Questions to Ask People
2. What kind of music do you find yourself listening to the most?
Music is something we all connect with. It also tends to show our emotional and mental state.
Asking about music opens up conversation about his current likes. It also tells you about him without coming across as too strong of a question.
Music is great for a shared interest too.
Read also: 50 Funny Questions to Ask Your Girlfriend
3. What’s something you’ve always wanted to do but haven’t had the chance to yet?
Great questions take people off guard in a good way. They make them think.
This question will help you learn more about him and what he likes. It also opens him up to talking about something he is curious about that he hasn’t tried.
Asking this helps build emotional curiosity.
4. What’s the coolest place you’ve ever been to?
Similar to the previous question, this is a question that can only be answered with an interesting story.
While he may not have been to the coolest place in the world, he’s sure to have some good stories about somewhere he’s been.
This is also a fun way to transition into talking about other cool places or adventures.
5. What do you do to unwind when you’re stressed?
This question not only brings emotion into the conversation, but it helps you understand how he deals with his emotions.
Understanding how he handles stress can tell you a lot about his maturity and personality.
Plus it subtly pulls on emotional awareness during your communication.
6. Is there something people don’t normally understand about you?
Asking him this question can help him open up about things people may not know about him.
We’ve all felt misjudged before and telling someone things they don’t know about you is an easy way for a person to feel like they understand you.
It’s subtle but helps create emotional connection during conversations.
Read also: 101 Deep Questions to Ask Your Best Friend
7. What would your perfect day look like?
This question is great for learning more about him and what he enjoys doing.
It also allows you to pick up on what he values as an ideal day.
Ask this and you can learn a lot about his personality.
It also helps you build relationship compatibility awareness.
8. What’s something you wish you were better at?
This question subtly brings the conversation towards growth and learning.
Not only will you learn more about what he’d like to improve about himself, but you can also gently guide the conversation towards things he wishes he knew when he was younger.
Self improvement builds emotional connection.
9. What’s something that makes you laugh?
Laughter is contagious. When you ask a guy this, you not only learn more about what makes him tick, but you can also enjoy laughing with him.
Find out what makes him laugh and use it to your advantage. Not only will you have a good time, but it creates a positive emotional association with you when you make him laugh.
Plus the more you can make a guy laugh, the better.
10. What type of people do you enjoy spending time with the most?
When you ask guys questions about themselves, you not only learn about who he is, but you can learn about what he values in others.
You can learn about his friendships and what he looks for in others by asking him this question.
You can learn more about what he values in a person by asking him this.
11. What’s the best piece of advice you’ve ever received?
There’s something about asking someone for advice they’ve received that not only tells you what they value, but it can also lead to some pretty cool stories.
We all love to talk about that one piece of advice someone told us that we couldn’t forget.
This question will help lead the conversation in a deep direction.
12. What do you think makes a relationship work?
Alright, guys, we got one deep question in there.
This question is great for learning what he values in a relationship and what he believes is needed for a relationship to work.
You’ll know when the time is right to ask him this question. If you two have been talking for a while and he seems comfortable and engaged, slip this question in there.
Not only will you build emotional connection through answering this, but you learn about his views on relationship values and emotional maturity.
13. What’s a random talent you have?
Everyone has weird things they can do or random talents. It’s a fun question to ask just to see what he says.
Not only can you potentially discover some funny answers, but it will help keep your conversation light and fun.
This is always a good question to ask if you feel like the conversation is starting to become too serious or heavy.
14. What inspires you?
We all have things that keep us going. There is power in understanding what drives your guy.
Ask him this and you can learn what makes him tick.
Understanding what drives him can help you learn what motivates him in life.
15. What are you working on bettering about yourself right now?
Similar to one of the earlier questions, this question allows him to open up about things he wishes he could improve about himself.
You can learn what areas he’s working on and use that to subtly learn what he wishes he knew about sooner.
This question stems into self improvement habits.
16. How do you like to spend your weekends?
This question is great for understanding how he likes to balance productivity and relaxation.
Learning about how he likes to spend his weekends can tell you a lot about his personality and lifestyle.
If he likes spending his weekends relaxing, you might not vibe as well on weekends.
Understanding how he spends his time will allow you to pick up on compatibility in daily life.
17. What are you passionate about?
Ask any guy what he’s passionate about and watch them come alive.
When we talk about things we love, we tend to go into detail and talk more.
By asking him this question, you can learn what he loves and have him open up more.
He’ll open up to you more just by asking this one question.
18. What’s a memory you have from childhood that you still think about?
Colorful questions about his childhood are great for understanding his past.
Asking about his past helps him open up emotionally and allows him to talk to you about possibly fun and silly stories.
This question will not only open him up but it will also allow him to feel more comfortable with you.
Memories open up emotional conversation.
19. Is there something you wish others would know about you?
As humans we all want to feel understood.
By asking this question you are allowing him to open up about things people may not know about him.
This not only leads to a better emotional connection but it can help you understand him on a deeper level.
Understanding each other is important for emotional connectivity.
20. How do you like to relax?
Similar to one of the questions above, this question allows you to learn what he likes to do after a long day.
You learn more about what he likes to do to unwind and relax after a long day at his job.
If he likes to relax by spending time alone, then that could be a compatibility issue down the road.
Learning how he relaxes can help you understand compatibility in daily life.
21. What are you proud of that you don’t often talk about?
This question is great for opening up conversation about things he likes but may not talk about often.
It can range from achievements to cool experiences he’s had.
Not only can you learn about some cool stuff he’s done, but he’ll feel comfortable with you knowing cooler things about him.
Emotional depth is established when we open up to others about our accomplishments.
22. What are your goals right now?
Goals are something we all should have. Understanding what his goals are can tell you a lot about what he focuses on.
You can learn if he’s goal oriented or not by asking him this question.
If he doesn’t have goals or doesn’t know what he’s working towards, you’ll know his life direction.
Understanding a guy’s current goals can help you know his life direction.
23. What food do you love that you could eat every day?
Food is life. We all love talking about and eating our favorite foods.
This is great for opening up conversation about his favorite food but can also lead to other fun topics like cooking or restaurants.
He’ll love talking about food as much as you will.
Keep the conversation going by discussing something as essential as food.
24. What’s a movie or show you can watch over and over?
Everyone has that one movie or show they can watch over and over again.
This question not only helps you learn more about him but it can help you discover common interests.
With this common interest, you can talk about your favorite parts of the movie or show and suggest watching it together.
Watch how easy it is to keep conversation flowing by asking about entertainment.
25. What’s something that makes your day?
This question is great for closing out a conversation but can also be used throughout.
You not only learn what puts a smile on his face, but you can continue to ask him this question when his day is rough.
Watch how you can change his day by just making him think about something that normally makes him happy.
Understanding how you make each other happy is important for a positive relationship.
Conclusion
Conversation doesn’t mean talking more. It means asking better questions.
Once you stop asking boring small talk questions and start asking better questions that show interest in him and his lifestyle, he will talk all day.
There is beauty in balance. You want to ask questions that make him curious but don’t push too hard. You want to ask questions that have some depth but aren’t too intense. You want to care about what he has to say but don’t overanalyze every answer.
You want a conversation to flow.
Try these out and you will notice yourself having better conversations without even trying.
FAQ
How do you keep conversation going with a guy?
By asking him questions that require more than a yes or no. Show interest and be curious about the things he has to say.
What questions make a guy open up?
Questions about what he likes, his goals, advice he’s been given, his childhood, his values, and what he spends his time doing.
How do I stop awkward silence when talking to someone?
Don’t ask yes or no questions. Ask follow up questions. Ask him about what he likes.
Silence in conversations happens when there is no emotion or direction to go.
What questions should you not ask a guy on a date?
Too personal too soon. Questions that come off as judgmental or interrogative should also be avoided.
Are guys attracted to deep conversations?
Yes, but only when they feel comfortable and not pressured.
How do I know if he likes talking to me?
He won’t give short responses and will keep talking to you. He will ask you questions in return and want you to keep talking to him just as much as he is.
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