Whether you’re swiping through dating apps or out on the town, I’m here to elevate your chat game so you can make smart decisions about who to let into your life.
These 120 deep questions to ask a guy before dating will reveal his values, beliefs, and priorities.
So, let’s peel back the layers of that onion of a man to get to the soft core of his being.
Deep Questions to Ask a Guy Before Dating
Whether you met him over dinner or swiping on a dating app, asking the right questions can reveal if he’s worth your time or if you should change your phone number and join witness protection.
Swap the typical “How was your day?” with these 30 actually important questions to ask a guy before you start dating him:
- Why did you swipe on my profile?
- Your profile mentions you love photography. What sparked that passion?
- How do you typically like to spend your weekends?
- If you could book a trip tomorrow, where would you go?
- What’s a book or movie that has made a significant impact on you?
- What are some personal development activities you’re currently into?
- What’s on top of your bucket list?
- In your opinion, what does success look like to you, both personally and professionally?
- How do your spiritual or religious beliefs shape your life and decisions?
- How important is family to you, and how do you stay connected with them?
- What's a valuable lesson you’ve learned from your past dating experiences?
- What qualities do you value most in a friendship?
- What's your love language and how do you like to show affection?
- What's your approach to resolving conflicts in a relationship?
- Describe your perfect date night. Is it a cozy night in or a night on the town?
- What are your three nonnegotiables in a relationship?
- What are some of your big goals for the next few years?
- What's your vision for your future family?
- What drives you when working toward your goals?
- What’s something that scares you but you’re actively trying to overcome?
- What's a significant lesson you've learned that has shaped who you are today?
- What's the most spontaneous or adventurous thing you've ever done?
- How do you manage stress?
- How do you ensure you have a good balance between work and personal time?
- How do you balance your financial goals with enjoying life?
- After a long day, how do you like to unwind and relax?
- What are some habits or routines you follow to stay physically and mentally healthy?
- What is your relationship to alcohol and drugs?
- Is there a cause or issue you're passionate about and actively support?
- What are your thoughts on marriage and long-term commitment?
When it comes to dating, asking the right questions isn’t just a smart move — it’s a science-backed way to make real connections and find true compatibility.
The way you frame your questions can significantly impact the depth and quality of the answers you receive.
According to a study published in the journal Current Opinion in Psychology, questions that are open-ended and neutral tend to elicit more honest and informative responses. This approach avoids leading questions and negative assumptions, creating a more comfortable and truthful dialogue.[1]
In essence, being intentional and thoughtful with your questions can transform your dating experiences from superficial encounters to profound connections.
So, before you jump out of your comfy sweatpants for that Hinge date, interview your potential Prince Charming with some meaningful questions to avoid wasting your effort on an hour of excruciating awkwardness.
Deep Flirty Questions to Ask a Guy
So, you’ve hit it off, and the chemistry is electric. The birds are chirping, and you’re dancing on the street like that unforgettable scene from 500 Days of Summer.
Here are 30 deep and flirty questions to ask to get to know each other better and make your connection sizzle:
- What was your first impression of me when we met?
- If we were to spend a day together with no plans, what do you think we’d end up doing?
- What’s the most romantic thing you’ve ever done for someone?
- Do you believe in love at first sight?
- What’s your dating trick that makes the ladies swoon?
- If you could describe how you feel about me in three words, what would they be?
- What’s something you’ve always wanted to try in a relationship but haven’t yet?
- How do you feel when we're apart? Do you get that same bubbly, floating feeling like I do?
- What’s on the menu for our next date?
- What do you think makes our chemistry so electric?
- What’s one lesson from your past that you’re excited to apply?
- How do you define intimacy beyond just the physical?
- What’s a personal experience that has shaped the amazing guy I'm getting to know?
- What’s the one thing about me that you can’t stop thinking about?
- What runs through your mind when you see me?
- Which kiss of ours has left you absolutely breathless?
- What’s your dream scenario for a romantic weekend together?
- Where do you see us in a year from now?
- If we could fast forward to any moment in our future, what would you want to see us doing?
- What’s a dream you’ve had about us that made you wake up smiling?
- What’s the most adventurous thing you’ve ever done, and can we top it together?
- What’s something you haven’t told me yet because you thought it was “too romantic”?
- What song always makes you think of me and puts a smile on your face?
- Is there a hobby or activity you've always wanted to try that we could pick up together?
- What’s your favorite romantic movie that we should watch together?
- What’s your idea of a cozy Sunday together?
- If we were characters in a romantic movie, what would our story be?
- What was the moment you realized you wanted to go on a second date with me?
- Do you identify yourself as more of a hugger or a kisser?
- What's the best compliment you've ever received, and can I top it?
Authors of a study from the Journal of Social and Clinical Psychology state that curiosity is “the genesis of intimacy.” Asking deep, genuine questions about your partner not only helps you know more about him but also sparks a desire to dig deeper, creating exchanges that foster lasting intimacy.[2]
Adding a touch of flirtation enhances this experience, blending excitement and infatuation with vulnerability. This unique mix leaves you feeling both enamored and intimately connected.
Try these deep, flirty questions to get to know him better in a playful, sweet way.
Deep Personal Questions to Ask a Guy
Your fire has been ignited, and it looks like it’s going to keep on burning, but you want to make sure that he is a real long-term prospect before you throw yourself with your whole self.
These 30 questions can help you both explore your personalities, values, and experiences on a deeper level. This will solidify your bond and help you understand each other more profoundly to see how it bodes for the future.
- What’s your favorite childhood memory?
- How did your parents influence who you are today?
- What was the biggest lesson you learned from your family?
- What’s your relationship like with your siblings?
- What family traditions do you cherish the most?
- What are your core values?
- What do you bring to the table?
- What are the three things that you like most about yourself?
- What are the three things that you dislike most about yourself?
- How do you define success in your life?
- What’s a recent moral dilemma you faced in your life and how did you handle it?
- What are your long-term career goals?
- Where do you see yourself in five years?
- What personal goals are you currently working on?
- What’s something you’ve always wanted to achieve?
- How do you stay motivated and focused on your goals?
- What’s the most important quality you look for in a partner?
- How do you handle conflicts in a relationship?
- What’s one lesson you’ve learned from past relationships?
- How do you want to be remembered?
- What’s the most embarrassing moment in your life?
- When did you last cry in front of another person? By yourself?
- What, if anything, is too serious to be joked about?
- If you were to die tonight, what would you regret not telling someone? Why haven’t you told them yet?
- If your house was on fire and you could save one item after your loved ones and pets, what would it be and why?
- Of all the people in your family, whose death would you find most disturbing? Why?
- How do you feel about your relationship with your mother?
- How do you feel about your relationship with your father?
- How would you feel about trying couples therapy together?
- For what in your life do you feel most grateful?
- If you could live to 90 and keep either the mind or body of a 30-year-old for the last 60 years, which would you choose?
Understanding his background and motivations is key to figuring out if he’s a keeper.
Julian Turecki, a certified relationship coach and popular podcaster, recently tweeted,
Much of dating culture today is shallow and avoidant. People have never been more starved for meaningful connection while simultaneously settling for casual, meaningless “situations.” They crave to be seen and yet are too fearful to open up and be vulnerable.[3]
So, dare to be vulnerable, don’t be afraid to ask genuine questions about things that truly matter because this is the only way to create meaningful connections.
Deep Questions to Ask a Guy Over Text
In today’s world, texting is almost as important as face-to-face conversations. It gives us a chance to think things over, choose our words carefully, and have unhurried chats.
So don’t hesitate to use technology to your advantage.
Here are 30 deep questions designed to spark introspective and insightful conversations perfect for those late-night texting sessions:
- What's something you wish more people understood about you?
- What's the last dream you remember having?
- What’s a decision you made in the past that you wish you could change?
- If you could have dinner with anyone, dead or alive, who would it be and why?
- What do you think is the key to a happy life?
- What’s the most meaningful gift you’ve ever received?
- How do you handle stress and pressure?
- What’s one thing you’ve never told anyone?
- What does your perfect day look like?
- If you could change one thing about the world, what would it be?
- What’s a song that you feel represents your life right now?
- What’s the most challenging thing you’ve ever done?
- What’s your biggest fear for the future?
- If you had unlimited resources, what project or cause would you work on?
- What’s a quote that resonates with you and why?
- What’s your favorite memory from the past year?
- How do you define love?
- What’s the most important lesson you’ve learned so far?
- If you could live anywhere in the world, where would it be and why?
- What’s a skill you wish you had?
- What’s your favorite way to spend a weekend?
- What’s something you’ve always wanted to do but haven’t yet?
- What’s a cause you’re passionate about?
- What’s the most spontaneous thing you’ve ever done?
- What’s a tradition that’s important to you?
- What’s the best piece of advice you’ve ever received?
- If you could have any job in the world, what would it be?
- What’s a book that changed your perspective on something?
- What’s something you’re grateful for right now?
- What’s the hardest thing you’ve had to forgive someone for?
Texting often gets a bad rap compared to face-to-face interactions, which indeed have their unique perks, such as reading body language, but let’s give texting some credit!
It allows us time to think, leading to more meaningful responses and turning simple chats into genuine conversations.
A study in the journal Computers in Human Behavior found that couples who engage in meaningful text conversations report higher relationship satisfaction and a stronger emotional connection.[4]
This highlights the power of thoughtful texting in building deeper bonds.
So don’t underestimate the potential of a well-crafted text.
Conclusion
Asking profound questions from day one is super important, confirming you’re on the same page when it comes to relationship values and future goals. These deep questions to ask a guy before dating are perfect to determine his values and beliefs.
Insisting on having deep conversations early on can really improve your chances of building a meaningful connection and a healthy, fulfilling relationship.
Check out our page to learn more about being in a relationship.
FAQ
What questions do men like to be asked?
Men like to be asked questions that show genuine interest and willingness to understand them better. Fun questions to ask include those about their hobbies and favorite movies, but also deep, personal questions about their values, life goals, and personal growth.
What are the most important questions to ask a man?
The most important questions to ask a man are those that explore his values, priorities, and relationship goals. These questions help you understand his objectives and gauge your compatibility, fostering a deeper connection and meaningful conversations.
What questions do I ask a guy to keep him interested?
To keep a guy interested, ask engaging questions about his passions, dreams, and experiences. Mix in some flirty questions and deep, personal ones about his values and life goals to foster a deeper connection. These creative, thoughtful, and deep questions to ask a guy keep the conversation lively, fun, and genuinely engaging.
References
1. VanEpps, E. M., & Hart, E. (2022). Questions and deception: How to ask better questions and elicit the truth. Current Opinion in Psychology, 47.
https://doi.org/10.1016/j.copsyc.2022.101383
2. Kashdan, T., & Roberts, J. (2004). Trait and state curiosity in the genesis of intimacy: Differentiation from related constructs. Journal of Social and Clinical Psychology, 23(6).
https://doi.org/10.1521/jscp.23.6.792.54800
3. Turecki, J. [@JillianTurecki]. (2024, July 25). Much of dating culture today is shallow and avoidant. People have never been more starved for meaningful connection while simultaneously . . . [Tweet]. Twitter.
https://x.com/JillianTurecki/status/1781323786580586994
4. Schade, L., Sandberg, J. G., Bean, R. A., & Busby, D. M. (2012). Texting, sexting, and attachment in college students’ romantic relationships. Computers in Human Behavior, 28(2), 444–449.
https://doi.org/10.1016/j.chb.2011.10.015
