Questions to Ask a Guy – Get Him Talking and Thinking About You

When you first meet a guy – and after the initial exchange of pleasantries, such as asking about profession, hometown, number of siblings, etc. – it can be challenging to know which questions to ask a guy to keep the conversation moving to a positive and intimate place.

With the right approach and some slight adjustments along the way, questions can help a budding connection properly blossom. Let’s look at questions to ask men that cover a whole range of topics and approaches, depending on your relationship and the conversational tone.

Some general tips for good questions to ask a guy

Before we get started on our list of questions to ask a guy, we would be remiss if we didn’t first give you some tips on how and when to ask them. It’s good to use common sense in these situations but here are some general things to guide you on finding questions guys love to be asked.

• Remember that the true point of these questions is to make your date more entertaining and help you really get to know them. Don’t let the act of asking questions get in the way of that goal.
• Whatever questions you ask, make sure they can lead to further questions and deeper conversation. These are called open-ended questions.
• Try to find common ground as quickly as possible when thinking about which questions to ask a guy. This will bring you closer and provide a good platform for conversation over shared interests. 

There are also signs people can show when you happen to be asking the wrong questions, as well as certain social faux pas to avoid during your interactions.

• Don’t badger them with questions. Conversations are an exchange, so try to quell your curiosity and let them also ask you questions about yourself, to build rapport and trust.
• If you asked the question, it could seem quite rude to the other person to not actively listen to the answer, or share any insight in response, so try to stay in the moment. 
• Don’t dive too deep. Try to ask questions when and where they seem appropriate for your intimacy level. For instance, you may want to wait for them to open a topic to conversation first before you probe deeper.

Okay, now that we’ve cleared up how to approach the right questions, let’s look into some material for the best questions to ask a guy you like.

Flirty questions to ask a guy

Whether you’re preparing for a first date or a little further along and want to take things to the level, flirty questions are a fantastic way to make your interest known without being obvious, especially when you say them in a teasing tone. Some flirty questions to ask a guy:

1. What do you notice first about a person?
2. What do you think are your best features?
3. What is the best and worst pick up line that you have ever heard or used?
4. Do you prefer it when I’m naughty or nice?
5. What’s something we have never done together that you would like to try?
6. What one thing about our relationship that you hope will never change?
7. What’s me something I don’t know about you, no matter how small?
8. Can you tell me the story of our first kiss?
9. How many times did you want to ask me out before you finally did?
10. What sets me apart from other people you’ve dated?

Romantic questions to ask a guy

Flirting on dates and over correspondence can be a lot of fun. But sometimes it’s time to get a little playful and go more direct. These are the types of questions you might ask later in the date or in subsequent interactions, as you grow more comfortable with each other and feel some kind of mutual interest.   

1. What makes you feel seen and loved?
2. Do you fall for people easily, or do you tend to play it more cautiously?
3. How do you want your next relationship to differ from your past ones?
4. Do you see me in your future? What does it look like with me there?
5. How would you describe falling in love? What does it feel like for you?
6. Could you see yourself being happy with someone like me?
7. What did you first think when you saw me?
8. What’s the best advice on relationships you’ve ever gotten?
9. What are your preferred love languages?
10. What’s something considered classically romantic that you’re just not into?

Questions to ask a guy to get to know him

It can be difficult to get to know a guy but open-ended questions are really useful; they are good ways to prompt your partner into sharing information he might not otherwise realize you want to know about him.

11. What’s the best thing you’ve read in the last five years?
12. If you could only bring three things with you on a deserted island, what would you pick?
13. What do you feel most passionate about?
14. Who is the most important person in your life and why?
15. What is something people would never guess just by looking at you?
16. Can you tell me about your best friend?
17. What is the weirdest thing you’ve put on a sandwich?
18. If you could be any animal, for a day, what would you be? And why?
19. Are you a night owl or an early bird?
20. How did your last relationship end?

Personal questions to ask a guy

As your relationship progresses, really getting to know your partner becomes more and more important. This is especially true if you’re planning on the relationship being a serious one, since your partner’s views and lifestyle could have an impact on yours for years to come.

21. Can we talk about our health histories?
22. Have you ever been in therapy?
23. How do you approach finances? Do you have debt? What are your financial goals?
24. What role will your family play in our relationship?
25. What are you afraid of?
26. What is something you wish you hadn’t done?
27. What do you want to improve or change about yourself?
28. What’s your relationship like with your family?
29. What’s your favorite way to destress from work?
30. How do you feel about surprises? Do you like to be surprised?

Deep questions to ask a guy

At some point, the time comes when you really want to know what makes your significant other tick. Deep questions like the ones on this list are a great way to spend some free time getting to know each other better – you could even order in food and make a date night of it.

51. When was the last time you did something that took you out of your comfort zone?
52. Do you believe in soulmates?
53. What would you say are your three most important values?
54. What traits do you think are most important to find in a partner?
55. What would you like people to say at your funeral?
56. What’s your relationship to religion?
57. Would you rather have a job that’s just a job but pays well, or be paid less to do something you’re passionate about?
58. What does your dream life look like?
59. Do you think it matters more what we achieve or who we surround ourselves with?
60. What are some things you wish you had known when you were younger?

Thoughtful questions to ask a guy

If you’d like to avoid asking too many personal questions, or if you think they’re making him uncomfortable, here are some reflective questions to ask a guy. These can be somewhat probing, but aren’t as directly demanding of them emotionally. They show you think deeply about things, but don’t need a conversation to revolve around being intellectually intense. 

1. What do you think we’re missing out on most as a society these days?
2. Do you think friends are the people we bind with forever, or do you think of existence as more of a solitary experience, where we’re more likely to float and occasionally meet?
3. Do you think it’s important to practice self-care?
4. Who do you think the most important living person is?
5. Do you think meditation really helps people?
6. What’s your favorite thing about living in this city?
7. How do you define success in life?
8. Are there any situations that just make you want to run away? Like when a place is too crowded?
9. Tell me something I don’t already know about you.
10. What do you think of the political landscape these days?

Interesting questions to ask a guy

Pique his interest while on the date. These are the questions to ask a guy to get him more engaged in the conversation. They’ll let you establish whether you share any intellectual compatibility, which will prove more and more important down the line.

1. Do you keep up with the news or do you find the world just moves too fast?
2. What piece of tech did you wait ages for, but feel underwhelmed by when it finally came out?
3. What do you think the child version of you would think of the adult version of you?    
4. What’s your opinion on the supernatural?
5. If you could move anywhere in the world for a year without worrying about money, where would you go?
6. Is there an objective limit to how good movie and game graphics can get before they just become surreal?
7. Do you think we’ll ever make it to the star systems in our lifetime?
8. Would you ever be willing to go live on another planet if we did?
9. What band or album changed your life as a kid?
10. What’s a hot take or unpopular opinion you have?

Fun questions to ask a guy

Sometimes it’s a good idea to keep the conversation light and fun, especially early on. Laughter can boost the vibe of a date or online chat. Here are some questions to ask a guy that veer more towards the fun side of things.

1. What’s the silliest movie you’ve ever cried over?
2. If you could live in one fictional world, which would it be?
3. What’s one rule you never follow?
4. What song do you always have lined up when doing karaoke?
5. Who’s one celebrity you just don’t get in modern pop culture?
6. Tell me one of your guilty pleasures.
7. What’s the dumbest opener you’ve ever heard on a dating app?
8. What’s your funniest story about your best friend?
9. What’s an extremely popular movie or TV show you’ve chosen to ignore?
10. What’s the weirdest thing you always laugh at?

Random questions to ask a guy

These are a bit like funny questions, though might seem like they came out of nowhere. These are great questions to ask a guy because, in some cases, their answers can show you how inventive and versatile they can be in their thinking.

1. What’s an embarrassing nickname you had as a kid?
2. Have you ever taken part in a viral challenge? If not, would you? 
3. Have you read something, or watched a movie that felt like it was written about you?
4. What’s one thing you’ve done this year where you may have gone one step too far?
5. How many Twinkies do you think you could eat in a single sitting if your life depended on it?
6. What’s a pizza topping I could choose in a restaurant that would make you cut ties with me?
7. What song might someone catch you singing in the shower?
8. Do you have any secret talents?
9. How did your childhood first crush break your heart?
10. What’s the one place in the world that makes you feel like a kid again? 

Silly and weird questions to ask a guy

If you feel like you have a shared passion for the silly and random, here are interesting questions you can ask that you might even find catches their random sense of humor off guard.

1. You have the keys to Doc’s DeLorean. Are we going to the past or the future?
2. You have to eat one ice cream flavor for the rest of your life. Which one is it?
3. Tell me the truth, or lie to me about something tiny and random in your life and I’ll guess if it’s true or not.
4. If you could change your full name, what would you change it to?
5. What’s one superpower you’re pretty sure you wouldn’t abuse?
6. Show me your most accurate animal impression.
7. What’s the cheesiest pickup line I could have used that would’ve worked on you?
8. What’s one talent you always figured you’d pick up at some point in life?
9. What’s your favorite word and why?
10. The last three emojis you used predict our next date. How’s it gonna go?

Questions to ask a guy during the different stages of your relationship

As we touched on earlier, there isn’t some overarching list of best questions to ask a guy. This is because the right questions so often depend on the right frame of mind. You build on this by creating an increasingly large frame of reference through intimacy. You also grow through an innate ability to gauge your partner’s emotional space.

Let’s look at the right kinds of questions to ask a guy at different stages of your relationship. 

Important questions to ask a guy before dating

This is when it’s important to vet the guy you’re talking to and check if he has any red flags, or holds any opinions that would make a relationship impossible.

1. Where do you see yourself in 5 years?
2. What kind of work are you currently in?
3. What are you looking for at the moment?
4. Do you plan on having a family someday?
5. What’s most important to you in a relationship?

Questions to ask a guy over text

This is when you’re getting to know him and doing some snooping, but you’re still keeping the conversation light and casual.

1. Would you say you’re a dog or cat person? Why?
2. Tell me something weird that happened in your week.
3. If you could recommend one movie to me, what would it be?
4. What are your friends like?
5. Is there anything about me you first noticed in particular?

Questions to ask your partner

These are some intimacy-maintaining questions, ones to help bring you closer as well as some that can help you assess the temperature of your relationship:

1. Do you believe in the idea that opposites attract?
2. What are some of your happiest memories from childhood?
3. How do you think your friends and family see me?
4. How did you and your last partner break up?
5. Is there anything I do that makes you feel invisible or unappreciated, in the moment?

At every point, you should compare answers answers to your own values, ensuring you’re never compromising your core values in order to maintain a relationship.

The most effective questions to ask a guy should come from your conversations

A good way to look at this list, is as a handy little cheat sheet of conversation starters you can keep in your back pocket if conversation peters out, or if you’d like to pivot a bit. Perhaps see if there’s a different avenue you may find compatibility on?

But when it comes to questions to ask a guy, it should never feel like you’re reciting from a list. Focus on getting to know him naturally and authentically. So only use these questions strategically, to light a bit of the proverbial flame beneath a promising new romance in your life.

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