226 Good Questions to Ask a Guy To Keep Him Interested

Looking for questions to ask a guy to know him beyond the surface level? Then you are in the right place. Let’s start by agreeing that asking guys questions can be quite a struggle. One reason is fear of coming across as “too desperate”. And we get it. But what if he is also interested and doesn’t know how to approach you? What if he’s online now searching for the same questions as you? What if he is also thinking about you? What if he’s dying to ask for your contact? What if…? So don’t let your fear make you miss a chance to connect.

You just have to remember that asking the right and thoughtful questions is very important when getting to know a guy. It allows you to know if his values and goals align with yours and see more of his personality. From there, he’ll likely pick up on your interest, and just like that, you’ve built trust, given him a safe space to express himself, and created a deeper emotional connection.

In this article, we’ll help you with a variety of questions to ask a guy so you can always come back to check and choose which one suits the level of relationship you want to have with him. The questions range from flirty to personal to deeper to small talk to interesting to good questions to ask a guy. So, let’s get right into it.

Questions to Get to know a Guy

Since it takes time to get to know a guy deeply at first, starting with simple open-ended questions to get to know someone new is really useful in this situation; they are good ways to prompt them into sharing information they might not otherwise realize you want to know about them. Before asking this question, ensure that you both must have been communicating and have bonded on mutual interests. That way there won’t be any weird vibes where you decide to let him know that you want to know him past the current level of relationship you have. These are some questions you would find relevant to ask to get to know a guy:

1. What’s the best thing you’ve read in the last five years?
2. If you could only bring three things with you on a deserted island, what would you pick?
3. What do you feel most passionate about?
4. Who is the most important person in your life and why?
5. What is something people would never guess just by looking at you?
6. Can you tell me about your best friend?
7. What is the weirdest thing you’ve put on a sandwich?
8. If you could be any animal, for a day, what would you be? And why?
9. Are you a night owl or an early bird?
10. How did your last relationship end?

Conversation Starters to Ask a Guy

Conversation starters are icebreakers. They open the door to the interaction between both of you, which is why they shouldn’t be personal or deep questions. They are just casual questions to ask a guy to kick off a regular conversation with him. While keeping it casual, pay undivided attention to what makes him happy. You can even mention that you’d like to add their favorite activities to your bucket list or suggest trying them together. With this, you’ve placed yourself in his mind as someone he could see taking things to the next level. Check out our list of conversation starters to ask a guy to get to know him better:

1. What’s your favorite way to spend a Saturday afternoon?
2. Do you enjoy podcasts or music more when commuting?
3. What’s a food you could eat every day and never get tired of?
4. What’s your go-to drink order at a bar or café?
5. Do you prefer summer or winter activities?
6. What’s your favorite sports team or athlete?
7. What’s the most interesting thing you’ve learned recently?
8. Do you enjoy playing or watching video games?
9. What’s your favorite local spot to hang out?
10. Do you prefer long walks or short hikes?

Personal Questions to Ask a Guy

As your relationship progresses, truly getting to know him becomes more and more important. That’s why asking the right questions to ask to get to know him is essential if you’re planning for the relationship to be a serious one, since his views and lifestyle could impact yours for years to come.

1. Can we talk about our health histories?
2. Have you ever been in therapy?
3. How do you approach finances? Do you have debt? What are your financial goals?
4. What role will your family play in our relationship?
5. What are you afraid of?
6. What is something you wish you hadn’t done?
7. What do you want to improve or change about yourself?
8. What’s your relationship like with your family?
9. What’s your favorite way to destress from work?
10. How do you feel about surprises? Do you like to be surprised?

Serious Questions to Ask a Guy

These are deep questions to get him to open up about himself and be vulnerable. It allows you to see him from another unique perspective and lets you know if you are compatible enough to move to the next level in your relationship. Bear in mind that when asking questions like this, you have to be serious and not make a joke out of his responses. They are deep questions for a reason.

1. What do you think makes a relationship truly work long-term?
2. What’s your biggest personal goal right now?
3. How do you usually handle conflict in relationships?
4. Do you believe in marriage? Why or why not?
5. What role does family play in your life?
6. Do you think honesty can ever hurt more than help?
7. What’s a challenge in life that shaped you the most?
8. Do you believe people can grow together in a relationship, or must they already align?
9. What’s your definition of commitment?
10. How do you want to be remembered?

Small Talk Questions to Ask a Guy

Many belittle small talk so much and just tell you to “go straight to deep questions to ask a guy to know him better” but the truth is that is not a good way to start any conversation. No one should skip having small talks because that’s the easiest way to know your common grounds and shared interests with them. According to Dr Gillian Sandstrom, a psychology professor at the UK University of Sussex, he says “ (Small talk) is something that we psychologists think is kind of fundamental. It’s like (how) we need food, we need water — we need to feel like we belong and that we matter to other people”¹

1. What’s your favorite pizza topping combo?
2. Do you usually watch movies in theaters or at home?
3. What’s your go-to karaoke song?
4. Do you enjoy road trips?
5. What’s the last show you binge-watched?
6. Do you enjoy trying new restaurants, or do you prefer familiar spots?
7. What’s your favorite ice cream flavor?
8. Do you like to plan your vacations or just go with the flow?
9. What’s your usual morning routine?
10. Do you prefer sweet or salty snacks?

Bold Questions to Ask a Guy

Bold questions spice up a relationship and help you see sides of each other that you’ve never known before. Now it’s time to take things to that level in your relationship, so you can throw in the bold questions. This is a subtle hint that you are interested in more than a friendship. But before asking that daring question, ensure you are on the same page as him(emotionally). The reason is so that you avoid any embarrassment if he reacts differently than you expect. Here are flirty questions to ask a guy that let him know you are ready for some exciting romance:

1. What’s the most spontaneous thing you’ve ever done?
2. Have you ever had a crush on someone unexpected?
3. What’s a secret ambition you’ve never told anyone?
4. Do you believe in love at first sight?
5. What’s the boldest risk you’ve taken in dating?
6. Have you ever sent a risky text and regretted it?
7. What’s the most daring thing you’d do for someone you like?
8. Do you think it’s better to play it safe or be bold in love?
9. What’s your most unforgettable first impression of someone?
10. What’s one thing you’d do differently in past relationships?

Romantic Questions to Ask a Guy to Get to Know Him Deeply

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?

Unpredictable Questions to Ask a Guy

Switch things up and throw in the curveball. Ask him random questions. They could be funny, personal, or weird questions depending on your relationship. Surprisingly men love unpredictability so this is your chance to use this to your benefit. To have an idea of what type of unpredictable questions to ask, skim through our list of random questions to ask a guy:

1. If you could live anywhere in the world for a year, where would it be?
2. What’s the strangest dream you’ve ever had?
3. If you could trade lives with a celebrity for a week, who would it be?
4. What’s the weirdest food you’ve ever tried?
5. Would you rather fight one horse-sized duck or a hundred duck-sized horses?
6. If you could instantly switch careers, what would you choose?
7. What’s the funniest thing that has happened to you at work?
8. If you had a personal theme song, what would it be?
9. Would you ever go skydiving or bungee jumping?
10. What’s the quirkiest talent you have?

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?

Intriguing Questions to Ask a Guy

As interesting as you want to make these questions, they actually do have an impact on a guy. It doesn’t really need to be funny, they could be questions about how he deals with his challenges orpassions. This makes him see that you really are interested in knowing more about him aside from the normal things he must have shared with you. In case you are still confused about what to ask a guy in this context, let’s help you with some:

1. What’s a belief you used to hold strongly but changed your mind about?
2. Do you think people are shaped more by nature or nurture?
3. What’s the most impactful book or movie you’ve ever experienced?
4. If you could see into the future, what would you want to know?
5. Do you think people are naturally good or bad?
6. What’s the most meaningful compliment you’ve ever received?
7. Do you believe everything happens for a reason?
8. If you had unlimited resources, what problem would you try to solve first?
9. What’s the hardest truth you’ve ever had to accept?
10. What keeps you motivated during tough times?

Silly and Weird Questions to Ask a Guy

If you feel like you have a shared passion for the silly and random, here are funny questions that you might even catch 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 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 a cat person?
2. Tell me something weird that happened in your week.
3. If you could recommend one movie to me, what would it be?
4. Which football team do you support?
5. Where are you traveling next?
6. What’s your favorite food?
7. What are you looking forward to this weekend?
8. Are you a beer or cocktail person?
9. What are your friends like?
10. Is there anything about me you first noticed in particular?

Questions to Ask a Guy you Like

You have a crush on him, but you want to move past that stage and build a deeper connection. Here are some good questions to ask your crush that can help him notice you:

1. What’s your idea of a perfect date night?
2. Do you believe in chemistry at first sight?
3. What’s the most romantic thing you’ve ever done for someone?
4. What kind of gestures make you feel special?
5. Do you like public displays of affection, or do you prefer privacy?
6. What makes you feel most appreciated in a relationship?
7. Do you enjoy surprises from someone you’re dating?
8. What’s your love language?
9. How do you know when you really like someone?
10. What’s the best compliment you’ve ever received from a partner?

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?

Deal Breaker Questions to Ask a Guy

In a relationship, both partners have deal breakers and expectations. So before getting too invested in a guy, both of you must sit down and know each other’s answers to your deal-breaking questions. This matters because his responses will give you an idea of whether your commitment could be long-term, if you’re compatible, and whether your values align. Once you notice that your future does not align, take that as a sign to walk away to avoid disappointment in the future.

1. Do you want children in the future?
2. How do you handle finances in a relationship?
3. Do you believe in monogamy?
4. Would you relocate for a partner?
5. How important is religion or spirituality to you?
6. Do you want to get married someday?
7. How do you usually spend your weekends?
8. Are you open to couples therapy if needed?
9. How important is career ambition to you in a partner?
10. What’s your stance on political differences in relationships?

Questions to Ask a Guy on a Dating App

You met him on a dating app, and now that you’ve both decided to take things further, you are running out of questions to maintain the vibe. Don’t panic. All you need are questions that will make him open up more about himself and also maintain the meaningful conversation and vibe that you both already have. We’ve got you. Here’s a list of open-ended questions to ask on a dating app:

1. What made you join this app?
2. What’s your go-to emoji?
3. Do you prefer texting, calling, or video chatting?
4. What’s your idea of a fun first date?
5. Do you usually make the first move?
6. What’s the most fun trip you’ve ever taken?
7. Do you like trying out new food spots?
8. What’s something not in your profile that would surprise me?
9. What’s your favorite way to relax after work?
10. Are you more of a morning or night person?

First Date Questions to Ask a Guy

Yes, first dates can be nerve-racking —and guess what can be even harder to come up with? First date questions. Behind that smile and shy laugh is a nervous soul wishing to sink into the ground because you’re not sure what to ask him. Don’t worry, it’s totally fine to feel that way especially if you don’t want to be too forward or make him uncomfortable. Here, we’ll help you with less awkward and simple  questions to ask so you can get to know him and keep the conversation flowing. This would even increase your chance of getting a second date. Here you go:

1. What’s your favorite thing to do on weekends?
2. Do you enjoy cooking, or do you prefer dining out?
3. What’s your go-to comfort food?
4. Do you enjoy live music or prefer a quiet evening?
5. What’s your favorite type of cuisine?
6. Do you like pets?
7. What’s your idea of a fun day trip?
8. Do you usually plan your outings or go spontaneously?
9. What’s the most memorable date you’ve ever been on?
10. Do you like trying new activities on dates?

Second Date Questions to Ask a Guy

You enjoyed each other’s company and now he’s requesting to go on a second date with you. At this point, he is definitely comfortable with you to an extent so you have a chance to ask a series of second date questions that would not be too personal, but at least deep enough to learn more about him. Guys love it when you are curious about them so be detailed with your questions. Focus your questions on his interests and his perspective on relationships. Remember not to interrupt when he speaks, and pay attention to the things he enjoys talking about. Here are second date questions that would probably lead to a third date:

1. What’s something you’ve always wanted to try but haven’t yet?
2. Do you enjoy weekend getaways?
3. What’s a hobby you’ve always wanted to pick up?
4. Do you prefer board games or card games?
5. What’s the most adventurous thing you’ve done recently?
6. Do you like cooking together on dates?
7. What’s your favorite memory from childhood vacations?
8. Do you believe in astrology or personality tests?
9. What’s a place in the city you want to show me?
10. Do you usually text often when dating someone new?

This or That questions to ask a guy

To add fun to the conversation, here are some ‘This or That’ questions to ask a guy that would help keep things light and engaging.

1. Coffee or tea?
2. Beach vacation or mountain getaway?
3. Netflix or YouTube?
4. Early mornings or late nights?
5. Pizza or burgers?
6. Cats or dogs?
7. Books or movies?
8. Comedy or horror?
9. Stay in or go out?
10. Sweet or savory?
11. Camping or a luxury hotel?
12. Sports or video games?
13. Summer or winter?
14. Concerts or theater plays?
15. Online shopping or in-store shopping?

What are the Best Tips for Asking Guys Questions?

As mentioned earlier, when asking guys the right questions, show genuine curiosity. But you know what’s even more important? Your tone, timing, and intention. Don’t come off as an interrogator, so keep your questions light and non-pressuring so he receives your intent positively. Remember, you’re dealing with a man, so patience is key. Here are some tips to keep in mind when asking a guy questions to get a better response

• Create a comfortable environment: Your environment determines the type of questions you should ask. If you intend to ask him personal questions,  ensure you are in a relaxed and less noisy environment. That way he can express himself without any interruption from a third party.
• Open-ended questions: These make room for further conversation. The questions can be simple, but his answers allow you to go into deeper discussions.
• Active Listening: Don’t suddenly cut in when he’s answering your questions. That is a huge turn-off. Give him time to talk and listen. If you see he is answering passionately, pay full attention and let him know that you are not just asking questions, you really want to know him deeper than the surface level.
• Mutual Contribution: A Conversation between two people means they both express themselves on the same level. Before asking a question about a guy, ensure it is a question you can answer aswell. That way you can bond on shared interests and experiences.

What Questions do Guys like to be Asked?

When asking a guy questions, remember that behind his tough personality is an emotional being who appreciates small gestures. They really love to be asked questions that reflect that you care about them, allow them to feel seen, valued and heard. Go for questions that are about things they love which could be their passion, favorite sports or past experiences and values. By doing this, you are not only getting to know him but also showing signs that you want a deeper connection.

• What do you enjoy doing in your free time? They like to know someone cares to know about their day and lifestyle
• What’s a goal you’re currently working toward? This gives them the idea that you are interested in finding out more about his personal growth
• What’s the best compliment you’ve ever received? This encourages him to share what makes him feel good about himself
• Who has been the biggest influence in your life? This lets you know what has shaped him into who he is today
• What’s your favorite childhood memory? This allows him to open up about his growing up
• If you could travel anywhere right now, where would you go? They like to know someone is curious about their bucket list and dreams
• What’s an accomplishment you’re really proud of? This lets him open up about his achievements and wins with you
• Who’s your favorite sports player? This shows you are genuinely curious to know about his passions
• What makes you feel appreciated: This tells him, you care about how he wants to be loved and valued

What questions do guys ask when they are interested?

When a guy is interested in you, he will go to great lengths to communicate and get your attention. Here’s how you’ll know he’s interested: He will suddenly become more attentive, noticing every little detail—from what you’re wearing to changes in your hair. He’ll compliment your smile, your energy, and even laugh at your smallest jokes. He’ll call just to hear your voice and share how his day went. He’ll make plans to see you, even if it’s inconvenient for him, and he’ll want to know more about the things that interest you. He’ll stare at you when you’re not looking, show extra care, and sometimes even get shy when talking to you (which is a big sign, since most men aren’t naturally shy so if he is, he’s already gone for you). Are you getting this exact vibe from a guy? Then he’s interested in you and wants to take things further. In addition, here are some common questions a guy will ask if he’s genuinely interested in you:

• How was your day? It is a classic sign he wants to be part of your everyday life
• Did you get home safely? This shows that he cares about your safety and well-being
• What kind of music do you like? With this, he’s looking for shared interests
• What do you do for fun? This helps him find ways to spend time with you
• What’s your idea for a perfect relationship? It reveals  he’s thinking of a long-term relationship with you
• Have you eaten? This could seem like a small gesture but it’s sweet enough to know he is thinking about your well-being(he might even initiate buying you dinner)
• Can I see you this weekend?  A direct sign that he wants to spend more time together
• What do you look for in a guy? A big giveaway that he’s gauging where he stands with you
• Can I call you?

Are there Specific Topics Guys Enjoy Talking About?

Yes, in fact most guys are very committed to specific topics that interest them. Their world often revolves around these interests, so they genuinely enjoy talking about them. For you, this can be a smart way to engage them and make the conversation more comfortable. Remember, these are not just topics they enjoy, but also subjects that matter deeply to them, so don’t treat them like a “random questions to ask a guy” session. Pay attention to the ones he prefers to talk about, and use those as a springboard to ask more meaningful questions. Some of the common topics guys enjoy talking about include:

• Sports
• Hobbies
• Cars
• Games
• Technology
• Personal growth
• Finances
• Movies
• Childhood memories
• Music

Before asking a guy if he likes you, you probably have noticed some signs from him. Or maybe not. Regardless, you still want to confirm if he actually likes you to avoid wasting your time and move on. Then go ahead. We understand you might be scared to bring it up but it’s better to know his intentions than to be confused. Think carefully about the questions you want to ask, be direct and honest. Don’t mince words. This is a serious conversation so treat it as one—talk about it in a private location to avoid distraction. If you are still struggling  with questions to ask a guy if he likes you, then we have a list to help you: 

1. Do you like spending time with me?
2. How do you feel when we hang out?
3. Do you ever see us as more than friends?
4. Have you told your friends about me?
5. Do you feel comfortable around me?
6. What was your first impression of me?
7. Do you get excited when we talk or text?

How to Ask a Guy What He’s Looking For?

Asking a guy you like about what he’s looking for in a relationship is essential. This helps you avoid conflicts, heartbreak, and mismatched expectations. Maybe he doesn’t plan on having a long-term relationship, or maybe he’s asking for more than you can give. That’s why it’s important to find out what he truly wants early on, so you don’t face deeper pain later. When asking, be polite and respectful, and don’t pressure him. Start by asking about his views on relationships, his long-term goals, where he sees himself in the future, and most importantly, what he expects from your connection. This way, you’ll be clear on whether to continue or let go of the relationship in its early stages. Here are some good ways on how to ask a guy what he’s looking for:

1. Are you looking for something casual or serious?
2. What does an ideal relationship look like to you?
3. Where do you see yourself in the next few years?
4. Do you believe in long-term commitment?
5. Do you expect any level of commitment from me?
6. What are your expectations in a relationship?
7. Do you see yourself wanting marriage and kids someday?
8. What role do you want a partner to play in your life?

How to Ask a Guy on a Date?

How to ask a guy out on a date can be hard, but there’s nothing wrong with giving it a shot. Be bold and reach out to him to check his availability. Be confident and suggest an activity or location (preferably something you know he enjoys). Keep it light and casual, but also let him know you’re serious about your approach, and don’t forget to follow up before the actual date. Here are questions you can ask a guy you like to go out on a date:

1. Would you like to grab dinner with me this weekend?
2. How about we go see that movie you mentioned?
3. Want to check out that new restaurant together?
4. Do you want to go for a walk or coffee after work?
5. Can I take you out for lunch one of these days?
6. Would you be up for trying that fun activity we talked about?
7. How does Friday night sound for hanging out?

How to Ask a Guy to Define the Relationship?

Defining the relationship means clarifying where you both stand in each other’s lives. It’s an honest question you ask a guy before dating so you both can express your expectations, level of commitment, and vision for the future of your relationship. Once you’ve had this talk, you can align on how the relationship should move forward. It’s best to have this conversation early on so you don’t waste time assuming you’re on the same page when, in reality, the feelings may not be mutual. If you don’t know what to ask, then here are direct “how to ask a guy what are we” questions you can use:

1. Where do you see this relationship going?
2. How do you feel about us right now?
3. Do you consider me your girlfriend?
4. Are we exclusive?
5. What are your expectations from me in this relationship?
6. Do you see a future with me?
7. Should we talk about what we both want moving forward?

How to Ask a Guy to be your Boyfriend?

Are you ready to take things to the next level with him? Then it’s time to ask him to be your man. You don’t have to wait for him to pop the question—if your heart wants it, go for it. You wouldn’t want to miss the chance to show your love for him either. Here’s how to go about it: express your feelings first, let him know how you feel whenever you see him, tell him how much you value him as a person and appreciate your bond (remember, men love to feel valued), and then ask the question. These are options for popping the boyfriend question:

1. Do you want to make this official?
2. Would you like to be my boyfriend?
3. How do you feel about us becoming exclusive?
4. Can we take things to the next level?
5. Do you see yourself committing to me?
6. How would you feel if we became a couple?
7. Are you ready to call me your girlfriend?

What Questions Should You Never Ask a Guy?

As much as you may want to know a guy, there are certain questions you should never ask him. These questions aren’t safe and can come across as insensitive. They could even push him away, make him uncomfortable, or even make him feel judged. In the long run, instead of building a bond, you might end up crossing boundaries, and you definitely wouldn’t want that to happen, right? Here are some serious questions you should never ask a guy:

• How much money do you make? This comes across as intrusive and materialistic, making him feel like you’re more interested in his finances than in him.
• Why don’t you look like your siblings? This is a straight-up crossing the line question especially if he’s never told you he had family issues. Trying to create one is very offensive.
• How many women have you slept with? This is too personal and may make him feel judged, uncomfortable, or defensive.
• When are you buying me something expensive?
   This shows you’re only after material things, which can push him away.
• Why can’t you be more like my ex? This would bruise his ego and comparing him to your past relationship is unfair and hurtful.
• Do you think she’s prettier than me? This creates unnecessary tension and puts him in an uncomfortable position.
• Why are you so emotional? This invalidates his feelings and can make him shut down emotionally.

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