30 questions to ask a guy to really get to know him
Clinically reviewed by Dr. Chris Mosunic, PhD, RD, MBA
When you're trying to get to know someone new, it can be hard to know where to start. Here’s a list of 30 thoughtful questions to ask a guy on your next date or meetup.
Starting a conversation with a guy you’re interested in can be intimidating — and if you’re not sure what to ask, it can feel impossible. Maybe you’re on a first date and want to avoid awkward silences, or you’re already in a relationship and looking for fresh ways to connect. Or, maybe, you just want to muster up the courage to say hi to that cutie in your neighborhood coffee shop.
The main thing to remember is that most people just want to feel seen. One of the best ways to show you’re interested is by asking thoughtful questions.
Whether you’re texting, hanging out in person, or navigating those early stages of getting to know the new man in your life, try to keep the interactions natural and engaging. You’re not just trying to find out information — you’re creating moments where you both feel comfortable enough to open up.
So, take a breath, relax your shoulders, and remember that the secret to a great chat is genuine curiosity. Keep reading for a list of questions to spark that connection and curiosity no matter where you are.
5 icebreakers to start the conversation
Icebreakers are the perfect way to kick off a conversation, especially if you’re feeling nervous or unsure about what to say. The goal here isn’t to get deep right away. It’s just to spark a little back-and-forth that helps you both feel comfortable and less self-conscious.
These questions are light, easy to answer, and can quickly set the tone for a relaxed, fun chat.
Here are five examples to get the ball rolling:
What’s a movie or TV show you can watch over and over?
What’s your go-to comfort food?
If you could live anywhere for a year, where would it be?
What’s one skill you’ve always wanted to learn?
What’s a fun fact about you most people don’t know?
Show genuine interest in his answers by asking follow-up questions or sharing your own thoughts. For example, if he mentions his favorite comfort food, you could talk about yours or ask if he’s ever tried something similar. This helps create a flow that feels natural and keeps the energy positive.
5 questions for discovering his passions and interests
Once the conversation is flowing, it’s time to dig a little deeper and learn about what drives him. You’ll probably want to ask him about his hobbies, interests, and passions.
Not only does this show that you’re interested in what matters to him, but it also helps you find common ground. Plus, people tend to light up when they talk about something they love, so it’s a win for both of you.
You’re not interrogating him — you’re just giving him the chance to share what excites and inspires him. Whatever it is, hearing him talk about what he enjoys most can tell you a lot about his personality and priorities.
To learn more about his interests, try asking:
What makes you lose track of time?
Are you more into sports, music, or something else entirely?
Who’s your favorite artist, athlete, or creator right now?
What’s the last thing you learned that really fascinated you?
If you had unlimited free time, how would you spend it?
As he answers, pay attention to what makes him smile. If he’s talking about his favorite band, you might ask what song he recommends or share your own favorite artist. If he loves sports, you could ask if he plays or just enjoys watching games.
This kind of exchange is also a great way to discover shared interests. If he loves hiking, maybe you can suggest a trail you’ve wanted to explore. If he’s a foodie, you could talk about trying a new restaurant, swapping favorite recipes, or even cooking together.
Even if you don’t have the same hobbies, listening with interest and asking follow-up questions can make a big difference.
💙 Do some self-care homework and listen to Passion Pull with Jay Shetty to uncover your unique purpose, too.
5 questions for learning his values and goals
When you’re getting to know someone, it’s important to understand their values. By asking about his values and goals, you can get a glimpse into what drives him.
It might feel a little nerve-wracking to bring up deeper topics, but most people appreciate the chance to share what they care about. You don’t have to dive in all at once. Ask a question when the moment feels right, and give him space to think and respond.
A few examples include:
What’s something you’re really proud of?
Who has influenced you the most?
What are you working toward right now?
If you could change one thing about the world, what would it be?
What’s something important to you in a relationship?
When you ask these questions, pay attention to how he responds. Does he light up when he talks about a goal he’s chasing? Does he seem thoughtful when discussing a value or belief that matters to him? These are signs that he’s opening up, and it’s an opportunity to connect on a deeper level.
You can also share your own experiences and goals. If he talks about a challenge he’s overcome, you might mention something similar you’ve faced. If he opens up about wanting to improve in a certain area of life, you could offer encouragement or talk about how you’ve tackled your own self-improvement journey.
5 questions to add a fun and playful twist
Sometimes, the best way to connect with someone is to just have fun. Playful and silly questions help keep the mood light and create space for laughter and memorable moments.
These types of questions are great for breaking up deeper conversations or just bringing more energy to a casual chat. They also let you see his sense of humor and how he handles creative or unexpected situations.
When you ask these types of questions, don’t be afraid to jump in with your own answers too. It’ll make the conversation even more engaging.
Here are five playful questions to try:
If you could have any superpower, what would it be?
What’s the weirdest food you’ve ever tried, and did you like it?
Do you believe in aliens, ghosts, or other supernatural things?
If you had to survive a zombie apocalypse, what’s your strategy?
What’s the most embarrassing thing that’s ever happened to you?
Even if the answers are goofy, they’re a chance to see his fun side and build rapport. Don’t worry about getting too serious here. It’s all about enjoying the moment and letting both your personalities shine.
To keep the fun going, play along with his answers. If he says he’d teleport as his superpower, ask him where he’d go first. If he tells you a wild zombie survival plan, challenge him on it or share your own. This back-and-forth keeps the conversation dynamic and engaging.
5 questions for flirting and showing your interest
When you’re ready to let him know you’re interested, asking flirty questions can be a fun and subtle way to test the waters.
These types of questions strike a balance between playful and thoughtful. They also create an opportunity for him to open up and share more about what he finds attractive or meaningful in a connection.
Flirty questions don’t have to be over the top or make the conversation awkward. The key is to keep them lighthearted and genuine while focusing on his preferences, experiences, and feelings. By doing this, you can create a safe and engaging space where both of you feel comfortable exploring your connection.
You might ask questions like:
What’s something you find irresistible in a person?
Do you think you’re more of a hopeless romantic or a realist?
What’s the best compliment you’ve ever received?
What’s a small thing someone could do that would totally make your day?
What’s your idea of the perfect date?
When asking these questions, don’t just focus on his answers. Use them as a chance to share a little about yourself too. For example, if he describes his perfect date, you might say, “That sounds amazing! Mine would probably be something like...” This keeps the conversation balanced and lets him get to know you better, too.
If he responds positively, it’s a good sign that he’s enjoying the flirtation and feeling the connection. Pay attention to his body language, tone of voice, or how engaged he is in the conversation. If he leans into the playful vibe or starts asking flirty questions of his own, you’re on the right track.
5 casual texts that’ll make him smile
Texting is a great way to stay connected and show interest, but figuring out what to say can sometimes feel tricky. Try not to overthink things. The goal isn’t to keep the conversation going nonstop. It’s to share a little positivity and build a connection over time.
Focus on asking light questions, sharing a little about your day, or referencing something he’s mentioned before. These types of messages show that you’re paying attention and genuinely enjoy chatting with him.
Here are five easy, casual texts you can send to brighten his day:
What’s a song that instantly boosts your mood?
If you had a lazy day today, how would you spend it?
What’s one thing you wish more people knew about you?
Who’s your favorite character from any TV show or movie?
If we could teleport anywhere for dinner right now, where would you want to go?
When texting, timing can also make a difference. Sending a message during a relaxed moment in his day—like after work or during a quiet evening—can make it more likely for him to respond thoughtfully.
Don’t be afraid to follow up on something he’s mentioned before. For example, if he recently talked about a hobby, say, “How’s that project coming along?” If he’s mentioned a stressful situation, you could check in with, “How did it go today? Hope it worked out!” These kinds of texts show that you’re paying attention and care about him.
Keep your tone upbeat and friendly, and don’t stress if he doesn’t reply immediately. A thoughtful text can mean a lot, even if the response doesn’t come right away.
💙 Take a five minute meditation break if you’re stressing about response times with Chibs Okereke’s Overcoming Negative Thinking.
Questions to ask a guy FAQs
What are some good flirty questions to ask a guy without overstepping?
Flirty questions can be a great way to show your interest while keeping the tone light and fun. To avoid overstepping, focus on questions that let him share his preferences or playful thoughts without making him feel uncomfortable.
For example, you could ask something like, “What’s the best compliment someone has ever given you?” or “What’s your idea of the perfect date?” These types of questions are flirty but still respectful, and they open the door for him to share more about himself while letting you express your interest naturally.
If he seems a little shy or hesitant, don’t push too hard. Instead, shift the focus to something more casual, like a different fun or playful topic. These 30 questions to ask on a first date might help you hit the right tone. Flirty questions work best when they feel natural, so trust your instincts and pay attention to his comfort level as you chat.
How do I balance serious and lighthearted questions during a date?
Balancing serious and lighthearted questions is all about reading the moment and letting the conversation unfold naturally. Start with fun, easy topics to help both of you relax, like favorite TV shows, music, or hobbies.
Once the vibe feels comfortable, you can transition to more meaningful questions by picking up on cues from what he shares. For instance, if he mentions something he’s passionate about, you can ask what inspires him or what goals he’s working toward. Or you might try one of these 30 questions to get to know him more deeply.
Don’t feel like you need to force serious topics if they don’t come up naturally. A great conversation often has a mix of laughter and meaningful moments, so let things flow. If you notice the energy shifting—like he seems deep in thought or starts talking about something personal—this could be a good time to ask a more thoughtful question. By keeping the conversation balanced, you’ll create a dynamic that feels genuine and engaging.
What’s a polite way to shift topics if the conversation feels awkward?
Awkward moments happen to everyone, so don’t stress if the conversation hits a lull. The easiest way to shift topics is to acknowledge the moment with a friendly tone and move on.
You might say something like, “That’s interesting! Speaking of…” or “This just reminded me of something. What do you think about…” This approach feels natural and keeps the conversation flowing without making the other person feel awkward.
You can also use humor to diffuse the moment, like jokingly saying, “Okay, I think we just hit our first awkward pause.” Humor shows that you’re comfortable and confident, which can make the other person feel at ease too.
Are there any specific topics guys generally enjoy talking about?
While every guy is different, many enjoy talking about topics they’re passionate about or find interesting. Hobbies, sports, music, movies, or gaming are often great starting points. Some guys might enjoy talking about their goals, favorite travel destinations, or even funny or unusual experiences.
If you’re not sure what he likes, start with open-ended questions like, “What do you usually do for fun?” or “What’s something you’ve been really into lately?”
Pay attention to his energy when he answers. If he lights up talking about a certain topic, let him dive deeper by asking follow-up questions.
Showing genuine interest in what he enjoys can make the conversation more engaging for both of you. Even if it’s something you’re not super familiar with, being curious and open-minded can go a long way in building a connection.
How can I tell if he’s genuinely interested in the conversation?
It’s often easy to tell if someone is genuinely interested in a conversation by their body language, tone of voice, and level of engagement.
If he’s making eye contact, leaning in while you’re talking, or nodding along, those are good signs that he’s invested in the conversation. Pay attention to his energy, as well. If he seems enthusiastic or animated when he’s talking, that’s a strong indicator he’s enjoying the interaction. So does him asking follow-up questions or sharing more than just quick one-word answers.
On the flip side, if he’s looking away often, giving short responses, or seeming distracted, it might mean he’s losing interest or just having an off day. If you sense this, don’t panic. Try shifting the topic to something lighter or more engaging to re-spark the connection.
Ultimately, genuine interest often feels mutual. If the conversation feels easy and both of you are contributing equally, chances are he’s as interested in getting to know you as you are in getting to know him. Trust your instincts and enjoy the process.
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