120 Questions to Ask a Guy On a First Date

Most men aren’t exactly open books. As someone who has been in a committed relationship with one for over a decade, I can attest that they often keep things to themselves. This can prove especially maddening when you first start dating someone. It can take time for both of you to open up and show your true selves to one another. Thankfully, we’ve got 120 questions to ask a guy on a first date to help speed that process up a bit. These questions act as icebreakers to help you get the conversation started if there’s a shortage of one!

These questions to ask a guy are intended to not pry too deeply, but instead, begin a conversation about a topic that both of you would be comfortable talking about. It’s much easier to scratch the surface than to go too deep too quickly so be mindful of the way you ask these questions and be prepared to have the tables turned for you to be asked the same question(s) in return. Dating can be a challenge but it does not have to be painfully awkward. Try these questions to ask a guy to learn more about him and to discover if you two could be a good fit or at least on the path to date number two!

Check Out These 120 Questions to Ask a Guy to Get to Know Him Better & Make a Good Impression!

Questions to Ask a Guy That Work as Icebreakers

• How was your favorite day ever, and why?
• What helps calm your nerves?
• What’s a good habit you’d like to adopt?
• What’s a bad habit you want to stop?
• Will you tell me one thing big or small that you’ve never told anyone else?
• How do you feel about couples who go on separate vacations?

Questions to Ask a Guy to Learn More About His Personality

• Is it easy for you to apologize?
• Who is your favorite author? What book written by them would you recommend?
• What’s the highlight of your life right now?
• Do you feel a partner should tell you about weekly or monthly expenses?
• Do you prefer indoor or outdoor activities? Why?
• Are you politically active? What causes are important to you?

Questions to Ask a Guy That Pry a Little Deeper

• What’s one thing that you don’t want your mom finding out about you?
• Are you an expert in any field?
• Will you tell me the scariest thing you’ve ever done?
• Should couples keep separate bank accounts? What about after marriage?
• Who in your life, that’s not family, do you always make time for?
• Do you play any instruments? If so, what? If not, what do you wish you could play?

Questions to Ask a Guy

• When you space out what do you daydream about?
• Have you known someone for a short time who has made a huge impression on you?
• Do you have a guilty pleasure Netflix show?
• How much input do you feel is appropriate for your parents to have on your relationships?
• What recent thing are you most proud of?
• Concert or sporting event?

Warm & Friendly Questions to Ask a Guy

• What’s your most favorite holiday tradition?
• What is something you are tired of hearing about?
• What always makes you laugh?
• Do you have any issue with your partner having close friends of the gender they’re attracted to?
• What’s the best purchase you’ve ever made?
• Do you have any siblings? Are you close?

Questions to Ask a Guy Who Won’t Open Up

• You are forced to pick a favorite Kardashian, who do you choose and why?
• Have you ever had a mic-drop moment? Will you tell me about it?
• What is one thing that always makes you smile?
• Do you believe in prenups before marriage?
• What “skill” would you say you have that’s actually useless?
• Do you believe in ghosts?

Questions to Ask a Guy to Learn Their Feelings About Material Things

• What is one thing that seemed silly until you tried it yourself?
• You awaken from a nightmare and you hear the most terrifying sound in the world to you. What is it?
• What is the worst gift you’ve ever received?
• What’s the best gift you’ve ever received?
• On a scale of 1 to 5 how important is paying off debt to you?
• Only if you’re comfortable, what’s the most difficult thing you’ve ever been through?

Questions to Ask a Guy When Things Get Serious

• Are you more of a money spender or saver?
• Imagine magic is real and you are able to learn a spell that does one mundane task. What would your spell be?
• Have you ever had a near-death experience that you’re comfortable sharing?
• How do you feel about adult children paying for their elderly parents’ care?
• Who do you text the most? What was the last thing you talked about?
• What food do you enjoy over all else?

Questions to Ask a Guy to Learn About His Outlook

• What’s the most horrifying dream you have ever had?
• Have you ever taken a long shot that paid off for you?
• If your life were a video game, what game would it be?
• How do feel about the domestic division of labor in a household?
• Who is your very best friend? Why?
• Cats or dogs?

Questions to Ask a Guy to Learn About the Life They Intend on Leading

• What is the worst injury to ever befall you?
• What would you do for $5 million?
• What would you not do for $5 million?
• Do you want to have kids?
• If so, how do you see your role as a father, and how does that differ from the role of your baby’s parent?
• How many kids do you want?

Questions to Ask a Guy About Relationships Past, Present, & Future

• Have you ever dated someone that members of your family did not approve of?
• What’s the best and worst thing about being your gender?
• How many times have you been in love?
• What color would you never paint any room in your home?
• What does the perfect relationship look like to you?
• Does that include marriage?

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Playful Questions to Ask a Guy & a Couple of Morbidly Serious Ones

• What secret identity would you have if you became a superhero?
• What childhood thing did you never grow out of and still enjoy?
• What is one thing that you’re proud of that’s made the world a better place?
• What do you hope is said about you at your funeral?
• What songs would you like to play at that funeral?
• What’s one thing that you’ve never been good at?

Random Questions to Ask a Guy

• What are your thoughts on monogamy?
• Do you have a nemesis? Who or what is it?
• What is one thing that we all do that we’ll laugh about in 20 years?
• What are three items you always have in your refrigerator?
• Are you religious? How important is that to you?
• What was your favorite children’s book as a child?

Questions to Ask a Guy That Prove the Devil’s In the Details

• Do you still talk to any of your exes? Is it important for you to end things on a positive note?
• How many phones have you broken or lost in your life?
• What movie could you watch on repeat forever?
• What app do you use most on your phone?
• What’s the dumbest thing you’ve ever done? How did you make it right?
• Would you care to share your thoughts on feminism?

Questions to Ask a Guy That Go Deeper

• What are some qualities from your ex that you’d like to find in a new significant other?
• In what movie will I find the universe you wish we could all live in?
• What’s one assumption many people make about you that’s wrong?
• What does your perfect morning look like?
• What are you hardest on yourself for?
• If you won a billion dollars, what would you do with your life?

Serious Questions to Ask a Guy to Gauge His Passion for Life

• What have your past relationships taught you about yourself?
• Has anyone completely lost your respect?
• What is the biggest doubt you have?
• What chore are you exceptionally good at completing?
• Do you have any serious expectations for yourself?
• What do you like to do on days off from work?

Questions to Ask a Guy About Work & Life

• If you could recreate any experience, what would it be and why?
• What is one thing people never guess about you?
• How far ahead do you plan in your life?
• What is your dream job?
• What do you expect from others?
• Do you procrastinate? What task do you put off doing more than any other?

Questions to Ask a Guy About His Present & Future

• What memory from adulthood makes you want to cringe?
• If tomorrow is your last day on earth, how do you spend the day?
• Do you have plans of retiring? What do you want to do at that time?
• Do you listen to anything on your commute?
• What do you hope to accomplish with your time on this Earth?
• What’s your dream vacation?

Questions to Ask a Guy to Determine If He’s Daddy Material

• What childhood memory still makes you cringe today?
• Do you have a favorite memory with a pet or animal?
• How do you feel about couples and marriage therapy?
• What are three of your favorite movies?
• Do you have a 5 or 10-year plan for your future?
• Do you like kids?

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Secret Weapon Questions to Ask a Guy

• Do you have any vices? Do you feel comfortable sharing one with me?
• If you were forced into exile on a desert island, what three things would you take with you?
• Who should wake up with a baby in the middle of the night?
• What are three of your favorite books?
• What was your childhood like?
• Did you take vacations? What was your favorite one?

There you go! We hope these questions to ask a guy will come to your aid on your next date. While we do recommend these questions for getting to know someone you’re just learning about, many of these questions will also work on your current boyfriend. It’s always nice when someone pays attention so you can return the favor by letting him talk about himself and then, following up with any relevant follow-up questions!