Maybe you’re chatting on a dating app. Maybe you’re meeting in person for the first time. Or maybe you’re a couple dates in. Whatever the situation is, you’ve probably found yourself in need of some questions to ask a guy to get to know him better. Especially if that guy is the host of Jeopardy!
Asking the right questions can help you gauge someone’s personality, interests, and values. And although there’s no set script for what to ask – no seriously, leave your screenplay at home – there are certain topics you may want to explore to get a better sense of who this new friend or romantic interest is.
We compiled a list of the best questions to ask a guy to help you learn more about him and help you figure out how compatible you are. They include prompts about career aspirations, hobbies, family, and a few random questions to see if he has any sense of humor at all and are a lot more interesting than “what do you do?”
Armed with these in your back pocket (because front pockets are never big enough), you can keep the conversation going all night long and well into your relationship. Or, however long you want. Some people just can’t make it past that pineapple on pizza question.
125 Questions To Ask A Guy
Questions to ask him on a dating app
- What made you decide to try out [insert name of dating app here]?
- What are your favorite hobbies or interests?
- Where were your born?
- What do you do for a living?
- Do you have any pets?
- Do you speak any other languages?
- Do you have any nicknames?
- Where’s your favorite place you’ve ever lived?
- Do you have any tattoos that I can’t see in your photos?
- What was your favorite subject in school?
- What’s your biggest dating pet peeve?
- How do you like to spend a lazy Sunday afternoon?
- What do you do for fun outside of work?
- What’s your favorite restaurant in town?
- If you could travel anywhere in the world right now, where would you go?
Questions to ask a guy on the first date
- What is your favorite type of cuisine or restaurant?
- What kind of music do you like to listen to?
- What’s the best concert you’ve ever been to?
- Have you traveled anywhere recently?
- Where is your favorite place to travel?
- What kind of movies or TV shows do you enjoy watching?
- What is your favorite book, and why?
- Do you have any pets?
- What is your favorite way to relax and unwind?
- What are you really passionate about?
- What is the most exciting thing you’ve ever done?
- What is your favorite way to stay active or fit?
- What is something that you’re currently learning or interested in learning?
- Do you have any hidden talents?
- What kind of sports do you enjoy playing or watching?
- What do you look for in a partner, and what are your deal-breakers?
- What makes a relationship great for you?
- What was your last relationship like and how did it end?
- Are you dating anyone else right now?
- What kind of connection are you looking for?
- Are you close with your family?
- Why shouldn’t I date you?
- What is something that you’re looking forward to in the future?
- What is something that you’re grateful for in your life right now?
- What are three things you couldn’t live without?
Questions to ask a guy to get to know him
- What is your favorite childhood memory?
- What is something that you are passionate about?
- What are some of your life goals and aspirations?
- What is something that you have always wanted to learn?
- What is your biggest accomplishment so far in life?
- What kind of qualities do you look for in a friend or romantic partner?
- What is something that you feel is important to share with others about yourself?
- What is your favorite way to relax or unwind after a long day?
- What’s your love language?
- What’s your biggest irrational fear?
- What kind of music do you like, and who are some of your favorite artists?
- What is your favorite book or movie?
- What do you enjoy most about your job?
- What kind of sports or physical activities do you enjoy?
- What’s a food combination that you just can’t get behind?
- What is your favorite travel destination, and why?
- What is your favorite way to spend a weekend?
- Do you have any siblings?
- Who have you been friends with the longest and why has it lasted so long?
Deep questions to ask a guy
- What do you think is the meaning of life?
- How do you define happiness?
- What is your biggest fear and how do you cope with it?
- Have you ever experienced a profound moment that changed your perspective on life?
- How do you deal with failure and setbacks in your life?
- How can I support you when you’re feeling stuck?
- What are your thoughts on spirituality and religion?
- Do you want to have kids?
- What motivates you to keep going when things get tough?
- What is your biggest regret in life?
- What do you think is the biggest problem facing the world today?
- Do you think it is possible to achieve true happiness without sacrificing something else in life?
- What are your thoughts on the concept of love, and how do you express it in your life?
- How do you balance your personal and professional life?
- What do you think is the most important lesson you have learned in life so far?
- Do you believe in the existence of extraterrestrial life, and what are your thoughts on the possibility of contact with them?
- How do you think technology will change the world in the next 50 years?
- What do you think is the most pressing social issue facing our society today, and how would you go about addressing it?
- What is your opinion on the role of government in shaping society, and how do you see its role evolving in the future?
- How do you think we can create a more inclusive and tolerant society?
- What is your personal philosophy on life, and how do you live your life in accordance with it?
Flirty questions to ask a guy
- What is your favorite part of my body?
- What initially attracted you to me?
- How would you describe me in three words?
- Have you ever been to a strip club?
- Describe your dream date with me.
- What do you think your best feature is?
- Have you ever had a dirty dream about me?
- What is your biggest turn on?
- What’s the dirtiest joke you know?
- What song always gets you in the mood?
- What are some of your bedroom fantasies?
- What did you wear to go to sleep?
- What’s your favorite time of day to get it on?
- What’s the wildest place you’ve ever hooked up with someone?
- Have you ever gone skinny dipping?
Random questions to ask a guy
- Is water wet?
- If you could invent a holiday, what would it be?
- If you could make the ultimate sandwich, what would be on it?
- What is your favorite room in your home?
- What is the best Wi-Fi name you’ve ever seen?
- How would you survive a zombie apocalypse?
- Pineapple on pizza: yes or no?
- What’s your favorite sounding word?
- What’s the worst drink someone can order at a bar?
- How many languages can you say “hello” in?
- What’s your go-to cereal?
- Do you pronounce GIF like “jif” (like the peanut butter) or “gif” (like gift)?
- How do you spell it: “OK” or “okay”?
- What’s the most amount of hours you’ve ever slept in one day?
- What’s the dumbest injury you’ve ever had?
Funny questions to ask a guy
- What’s your favorite pickup line?
- What is the most interesting thing you could do with 400 pounds of cheddar cheese?
- Who was your celeb crush as a teenager?
- If you could use magic to do one task, what would it be?
- What’s the weirdest item you keep by your bed?
- If you had to give up cheese or chocolate for the rest of your life, which would you pick?
- If you were arrested, what would it be for?
- What’s your favorite conspiracy theory?
- What reality TV show would you be on?
- What would be the tagline to the sitcom of your life?
- What’s the most embarrassing thing in your search history?
- What’s the most useless talent you have?
- The toilet isn’t working at someone else’s house. What do you do?
- What is the best excuse for being late that you’ve used?
- Have you ever seen a ghost?
Hannah Rex is Darcy’s Executive Editor. She has a background in journalism, content marketing, and SEO writing. She currently covers entertainment news, food news and trends, pop culture trends, and more. In addition to Darcy, she has written for companies including Beachbody, FitPlan, Soothe, Let's Eat Cake, and Her Campus. She also manages Darcy’s Instagram and weekly newsletters.
When not sitting behind a computer writing and editing, she’s an avid runner and yogi with an RYT 200 certification. Follow her on Instagram @hannah_rex and LinkedIn.
When not sitting behind a computer writing and editing, she’s an avid runner and yogi with an RYT 200 certification. Follow her on Instagram @hannah_rex and LinkedIn.
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