They say dating isn’t an interview, but it kind of is.
If you spend more time selecting nail polish than choosing a boyfriend, don’t be surprised that you end up the victim of a walking red flag.
I’m not saying you should interrogate the fella like a murder suspect, but having some creative open ended questions tucked in your back pocket can potentially save you a few months of therapy.
Table of Contents
Questions to Ask a Guy to Get to Know Him Better
What’s your favorite way to spend a weekend?What’s one thing you’re passionate about?Do you like to travel? If so, where’s the best place you’ve visited?What’s your favorite way to relax after a long day?What are your hobbies or interests?Are you more of an early bird or a night owl?What’s the most fascinating thing you’ve learned recently?- What’s one experience that has shaped who you are today?
- Is there a secret dream or goal you've always had but never pursued?
- What’s something you’ve struggled with that you wish more people knew about?
- How do you define love, and has that definition changed over time?
- What’s your biggest fear when it comes to relationships?
- Is there something from your past you’re still trying to make peace with?
- What’s a decision you’ve made that changed the course of your life?
- How do you handle stress or pressure in difficult situations?
- Who is the person you admire the most, and why?
- What’s your relationship like with your family, and how has it shaped you?
- Do you believe in soulmates or destiny in love?
- What’s your idea of a perfect day, and how often do you have one?
- What’s something about you that most people would never guess?
- What’s the hardest lesson you’ve ever learned, and how did it change you?
- What do you need from a partner to feel supported in a relationship?
- What’s a belief or value you’ve held onto since childhood?
- Is there a part of yourself you’ve struggled to accept or love?
- When do you feel the most vulnerable, and how do you deal with it?
- What’s something you wish you could change about yourself?
- How do you define happiness, and do you feel like you’ve achieved it?
- What’s the most meaningful compliment you’ve ever received?
- How do you think your closest friends would describe you?
- What’s a memory you cherish, and why does it stand out?
- Is there a part of your personality you feel misunderstood about?
- If you could go back in time, what advice would you give your younger self?
- What’s something you’re afraid to tell people because you fear they’ll judge you?
- How do you cope with feelings of loneliness?
- What’s the biggest risk you’ve ever taken, and was it worth it?
- What do you think is the most important thing for a successful relationship?
- How do you want to be remembered, and what kind of legacy do you want to leave behind?
Deep Questions to Ask a Man
How do you handle disagreements or conflicts in a relationship?What are your top three values in life?What’s the most meaningful compliment you’ve ever received?What’s your biggest dream or aspiration?How do you define trust in a relationship?Do you want to get married and/or have children someday?What’s your favorite way to practice self-care?What’s your favorite quote or mantra?What are your beliefs and values regarding sexual intimacy, and how do you see them fitting into our relationship?Are there any unmet needs or desires you have in our sexual relationship?
Flirty Questions to Ask a Guy
What's the funniest insult anyone's ever thrown at you?What three items would you buy together at a grocery store to make a cashier laugh?What would be the worst “buy one, get one” sale item of all time?If animals could talk, which one do you think would be the rudest?Do you judge people for putting pineapple on pizza?What’s one thing everyone looks stupid doing?What type of cheese are you and why?Would you rather be a little bit thirsty until the end of your life or have to high-five everyone you meet?What’s the most embarrassing thing in your closet?What’s the dumbest thing you believed about girls growing up?How does this look on me? (Include a photo of yourself in a flattering dress.)Are you interested in anyone right now? Asking for a friend.What was your first impression of me when we met?What’s something nonphysical that you find attractive?Has anyone ever told you how nice your eyebrows are?You were in my dreams last night. Want to hear about it?Do you consider yourself a good kisser?Is it okay that I kind of want to kiss you right now?Why is it that I love talking to you this much? Any theories?When am I seeing you next?What were you most excited to buy this year?Do you have a “bucket list,” and have you completed anything from it?If you had to delete all but three apps, which ones would you keep?What would be your dream job if money didn’t matter?If you could live anywhere in the world, where would you live and why?What’s one thing that never fails to make you cringe?If you had an unexpected day off tomorrow, what would you do?If you hosted a podcast, what would it be about?What is your favorite season?What is something you love doing but feel guilty about?Do you like weather?Do you like music or are you a cyborg?What color is your toothbrush?If pets are the new children and plants are the new pets, how many plants do you want to have?Can you touch your nose to your tongue?Pineapple on pizza: yes or no?Do you believe in life after love?Do you like getting jiggy with it?Why so serious?Do you ever feel like a plastic bag, lifting through the wind, wanting to start again?
Questions to Ask Before Dating
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Why did you swipe on my profile?
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Your profile mentions you love photography. What sparked that passion?
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How do you typically like to spend your weekends?
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If you could book a trip tomorrow, where would you go?
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What’s a book or movie that has made a significant impact on you?
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What are some personal development activities you’re currently into?
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What’s on top of your bucket list?
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In your opinion, what does success look like to you, both personally and professionally?
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How do your spiritual or religious beliefs shape your life and decisions?
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How important is family to you, and how do you stay connected with them?
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What's a valuable lesson you’ve learned from your past dating experiences?
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What qualities do you value most in a friendship?
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What's your love language and how do you like to show affection?
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What's your approach to resolving conflicts in a relationship?
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Describe your perfect date night. Is it a cozy night in or a night on the town?
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What are your three nonnegotiables in a relationship?
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What are some of your big goals for the next few years?
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What's your vision for your future family?
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What drives you when working toward your goals?
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What’s something that scares you but you’re actively trying to overcome?
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What's a significant lesson you've learned that has shaped who you are today?
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What's the most spontaneous or adventurous thing you've ever done?
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How do you manage stress?
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How do you ensure you have a good balance between work and personal time?
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How do you balance your financial goals with enjoying life?
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After a long day, how do you like to unwind and relax?
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What are some habits or routines you follow to stay physically and mentally healthy?
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What is your relationship to alcohol and drugs?
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Is there a cause or issue you're passionate about and actively support?
- What are your thoughts on marriage and long-term commitment?
Random Questions to Ask a Guy
If you had to describe yourself in three words, what would they be?What's the most spontaneous thing you've ever done?What's your guilty pleasure?What's the most interesting fact you know?If you could visit any fictional world, where would you go?If you could live in any era, which one would you choose?Who’s your favorite fictional character?What's your go-to karaoke song?
Personal Questions to Ask a Guy
What's something you wish people knew about you?Who has been the most influential person in your life?What's a goal you’re currently working towards?What’s a hobby or interest you have that people might find surprising?What's the best advice you've ever received?What's your favorite childhood memory?How do you maintain relationships with your family and friends?How do you handle conflict in your personal life?How do you typically spend your weekends?
Interesting Questions to Ask a Guy
How do you stay motivated and inspired?If you could master any skill instantly, what would it be?What’s one thing you think everyone should experience in their lifetime?What’s your preferred travel destination and why?What’s your favorite way to unwind after a long day?What’s the best book you’ve ever read and why?If you could have dinner with any historical figure, who would it be and why?If you could change one thing about the world, what would it be?What’s your ideal way to express creativity?What’s a cause you’re passionate about?
Weird Questions to Ask a Guy
If animals could talk, which one would be the rudest?If you could only eat one food for the rest of your life, what would it be?What’s the strangest compliment you’ve ever received?If you could have any fictional creature as a pet, what would it be?What’s the most bizarre talent you have?What’s the best sandwich?
Fun Questions to Ask a Man
What’s the funniest thing that has ever happened to you?What’s the most ridiculous thing you’ve ever bought?If you could create a holiday, what would it be called and how would it be celebrated?If you could be a character in any movie, who would you be?What’s your favorite board game or card game?If you could live in any sitcom, which one would it be?
Conclusion
Naturally, any of these open ended questions can be asked at any point in your romantic journey.
You decide, based on your vibe, how far you’d like to take it and when. These are just some suggestions to make sure you don’t end up with someone who’s inherently wrong for you.
Mix up your questions to keep things interesting. Throw in some deep questions to see if he’s got a soul, some flirty banter to check if he’s got game, and a dash of random weirdness to test if he can handle your quirky side.
Remember, though, it’s not just about the questions — it’s mainly about the answers. Listen to what he says and see if it aligns with your dreams and values.
Approach these chats with a mix of curiosity, humor, and openness, and you’ll be better equipped to dodge the Tamlins and find your High Lords of the Night Court.😍
Check out our page to read more about getting into a relationship.
References
1. Baxter, A., Maxwell, J. A., Bales, K. L., & Eastwick, P. W. (2022). Initial impressions of compatibility and mate value predict later dating and romantic interest. Psychological and Cognitive Sciences, 119(45). https://doi.org/10.1073/pnas.2206925119
2. Smith, A., & Anderson, M. (2018, March 1). Social media use in 2018. Pew Research Center. https://assets.pewresearch.org/wp-content/uploads/sites/14/2018/03/01105133/PI_2018.03.01_Social-Media_FINAL.pdf
3. Huang, K., Yeomans, M., Brooks, A. W., Minson, J., & Gino, F. (2017). It doesn’t hurt to ask: Question-asking increases liking. Journal of Personality and Social Psychology, 113(3), 430–452. https://doi.org/10.1037/pspi0000097
4. Catron, M. L. (2015, January 9). To fall in love with anyone, do this. The New York Times. https://www.nytimes.com/2015/01/11/style/modern-love-to-fall-in-love-with-anyone-do-this.html
5. Gersick, A., & Kurzban, R. (2014). Covert sexual signaling: Human flirtation and implications for other social species. Evolutionary Psychology, 12(3), 549–569. https://doi.org/10.1177/147470491401200305
