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Top 21 Questions To Ask A Guy - Start Really Wonderful and Romantic Conversations

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Robin is our female dating expert, style guru and resident life coach. Her expertise has been featured on Reader's Digest, Bustle, Hello Giggles, Best Life Online, Cheat Sheet, and many more. She lives with her fian ...
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by | | September 1, 2021


Our compilation of 21 questions to ask a guy will help you learn all the small, tiny things that make them. The thing is, getting to know a guy is a process, and it won't happen overnight.

But these questions can make the process more enjoyable. Not to brag, but we're not new to this - we've covered fun questions to get to know someone, how to start a conversation with a guy, and questions to ask a guy. And thousands of people have used our handy tips to know the deeper, more intimate parts of their significant other.

Let's dive in.

Contents

The Best 21 Questions To Ask A Guy

Trying to get to know a guy? There are only so many times you can text "what's up". Unfortunately, guys won't just come right out and start spilling their deepest secrets. And that's exactly what these 21 questions are for.  They'll help you uncover a guy's values, hopes, and dreams. And here's the best part - you won't run out of things to say. Plus, they will lead to a great conversation.

Here are the best 21 questions to ask a guy:

1. What is your biggest regret and why?

This is an interesting question that gives you a peek into the kind of person they are. After all, everyone makes mistakes. You want to see whether he acknowledges his mistakes and whether he accepts them and moves on or is consumed by regret.

2. How do you know if someone is your true love?

Find out what their love language is. Do they like words of affirmation, acts of service, or receiving gifts. This is an opportunity for you to discover the things you can do to show him you love him.

3. If you could listen to only one song for the rest of your life, what song would you choose?

This is a great conversation starter. Songs are an important part of our lives. In fact, we feel a little incomplete without our favorite songs. When you find out his favorite song, you'll find out the kind of music that gets him grooving or evokes deep emotions.

4. What is your most favorite memory?

Our memories make us who we are. Some of our fondest memories include birthdays, holidays, and anniversary celebrations spent with loved ones. This is your chance to relish the favorite childhood memory of the guy you love with the same fondness and intrigue he does.

5. Would you rather choose hiking or fishing?

Fishing and hiking have always gone hand in hand. They're both fun outdoor activities. Find out whether your significant other would rather head to the dock of a lakeside campground with his guy friends or go exploring in the woods.

6. What would be the scariest sound to hear after waking up?

Inject some humor into your conversation with this question. It creates an opportunity for a fun and engaging conversation about his biggest fear. Share your fears too to make the conversation more engaging.

7. What are your personal goals?

His goals are the expression of what he wants to achieve in life. Find out what his lifestyle, family, and business goals are. With this deep question, you'll be able to tell whether the two of you are compatible.

8. What did you wish last, like at your birthday or when throwing a coin into a fountain?

Discover what his heart's greatest desire is. This is a great way to find out what to get him as a gift. He'll be pleasantly surprised when you gift him something he has always desired on his birthday.

9. Would you rather live in the city or the suburbs?

Where you live often becomes a part of you. It shapes or even changes your life view. Having your guy tell you where he'd like to live will give you a clue as to what kind of life he'll be living years from now and whether the two of you are compatible.

10. What is your favorite movie line that you can't ever forget?

You can't go wrong with movies. Everyone has a favorite movie and a line that resonates with them. This conversation starter will begin a great discussion that can go on for hours.

11. If you created a miracle cure would you sell it and become a billionaire or give it to people for free?

This random question is a good way to bring in the money conversation. Any romantic relationship should have the same attitude towards money. There are no right answers, but if his answer resonates with you, then you have something good going.

12. Can you share what's the worst thing you've ever done?

Everyone has done something they're ashamed of. If he trusts you enough to share his mistakes, then it's a sign you have a good relationship and he trusts you. Ask the worst lie he's ever told too, and if he shares it, it means he absolutely trusts you.

13. What is the last car model you would choose if you were forced to have a single car for the rest of your life?

Most guys love talking about cars. And they can go on and on. These questions will lead to conversations about the make of car he drives, how much fuel it consumes, how many cars he's had, his favorite thing about his car, and others.

14. Are you the date-to-marry type?

Cough cough... romantic questions like this are a great way to raise the marriage issue. If you're looking to walk down the aisle at some point, this is the question you've been waiting for.

15. What high-level job do you think you could lie your way into with no experience and no one would notice?

Conversation topics about work are always fun to talk about. After you've laughed about him lying his way into becoming an astronaut, you can talk about his dream job and what you both plan on pursuing in the future.

16. Where's the best place you ever went to with your parents, and what did you do there?

Most people have a fond memory of their parents and it's usually toed to somewhere they went and something they did. Find out his favorite place that he went with his family and why that is particularly remarkable. This is a good time to learn more about his relationship with his parents.

17. What is your favorite comic book character?

Maybe he likes villains, or he loves Batman's resourcefulness. You'll never know until you ask. Make sure to ask why he loves the characters he loves. Most guys have more than one favorite. With this fun question, he'll appreciate that you want to know about his interests.

18. Have you ever had your heart broken?

Trod carefully when you ask this personal question. Heartbreak is never easy for anyone, whether you're the one who'd initiated it or you're the one who's been broken up with. Ask him about his heartbreaks and why the relationships ended.

19. What's the favorite sport that you played with your father?

Every guy has a favorite sport, and it's even more sentimental if he played it with his father. You're bound to develop a strong connection with him talking about this. This is a good question for you to know about his childhood and family.

20. Why are some people perfect for each other, and why are some people so toxic for each other?

This great question will help you determine the traits he finds toxic in relationships and those that he finds attractive in a partner. Relationship questions are always a good way to measure one's preference in a partner.

21. How long was your past relationship?

Personal questions like this may create some tension. It's always awkward talking about past relationships with your significant other. This question introduces the topics in a subtle and harmless way.

Downloadable and Printable List of Questions To Ask A Guy

Here is a downloadable and printable jpg/pdf list of 21 questions to ask a guy (right-click the image and select Save Image As...):

Frequent Asked Questions

Now you have a set of handy 21 questions to ask a guy. You'll never have to deal with an awkward silence during a date again. Even then, you probably have some questions about how to deliver the questions and how to conduct yourself. Check out the following FAQs.

What should you never ask a guy?

Never ask a guy questions that are a turn-off to a guy, even when he really likes you. Some questions, for instance, can leave him feeling uncomfortable or reveal things about you that are red flags.

When to play 21 questions game?

The best time to play the 21 questions game is when you're spending time together doing everyday things such as having coffee, eating out, or just lazing at home on a Sunday afternoon. If you're looking for a detailed guide on how to play 21 questions, you can visit our site here.

Can I ask 21 questions in a text?

Wondering how to text a guy? 21 questions is the perfect game for you. We've compiled a list of questions to ask a guy over text just for you.

How do you talk deep to a guy?

Start by learning how to talk to a guy before diving into deep questions. You see, beginning a deep conversation out of the blue may come off as too intense. Instead, set the stage with some small talk.  Check out some of our deep questions to ask.

What questions to ask a guy you are dating?

Don't know what to say to a guy you're dating? Our collection of questions to ask a guy on a date should do the trick.

How To Make 21 Questions To Ask A Guy More Interesting

The ability to ask questions without boring the guy to death is hugely underrated. You need to develop the skills needed for asking more interesting questions.

Here is how to make 21 questions to ask a guy more interesting: 

1. Avoid Steering as Much as Possible

A leading question subtly prompts the guy to answer your questions in a particular way. For example, “did you have any problems with your ex?” is a leading question since it presupposes that there were problems. The right question would be – “tell me about your relationship with your ex.

2. Dig Deeper with Follow Up Questions

Make a habit of asking follow-up questions unless you’re strictly looking for facts. For example, you might ask, “why do you think that is?” or “why do you say that?”

3. Less is More

Ask one question at a time. Avoid questions such as “What do you do for a living, what inspired you, and what do you hope to achieve?” You will confuse a guy and they'll be unlikely to answer any of your questions satisfactorily.

4. Listen and Don’t Interrupt

Avoid interrupting the guy when he’s talking. Ask a question and give him time to respond without constantly interrupting their train of thought. Listen to what he’s saying even when you think he’s veered off the topic. You can always redirect him back to the topic with a follow-up question.

5. Ask Open Ended Questions

Asking closed questions that can be answered with a Yes or No will be a yawn-inducing experience for him. You might also not learn much about him doing this. Questions with “should”, “is”, “would”, “are”, and “do you think” lead to a yes or no answer. Questions with “what”, “who”, “when”, “where”, “why”, or how to lead to more engaging conversations.

More Awesome Questions To Ask A Guy

We get it, you can never have enough questions in your arsenal. The following questions are designed for every situation. Check them out.

  1. 1. Like a guy? We've picked out the best questions to ask a guy you like, just for you.
  2. 2. You'll never run out of flirty things to say with our collection of flirty questions to ask a guy.
  3. 3. Your search for fun questions to ask your boyfriend ends here. You won't be needing another guide.

In Conclusion

Next time you want to have a conversation with your guy, refer back to our collection of 21 questions to ask a guy. You'll have plenty of fun questions to get to know someone. And that's not all, you get to learn how to start a conversation with a guy, and walk away with a ton of follow-up questions to ask a guy.

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