Getting to know someone takes time. But it also takes effort. If there’s a guy in your life you want to get to know better, then you’ll have to employ tactics other than small talk and politeness. To help you along the way, we’ve come up with a list of questions to ask a guy ranging from flirtatious, deep, personal, and then some.
What to be Mindful of When Asking Questions
Timing is crucial when it comes to asking someone a question. Sure, a question might be random no matter the time and place. But there’s a difference between a random question, and an inappropriately timed question.
Similarly, you want to read the room. Don’t suddenly change topics or bombard someone with question after question. This isn’t an interrogation, it’s a conversation. And conversations need a little back and forth between each person.
So, make sure your questions set the stage to keep the conversation moving forward. Of course, after diving into this list you’ll certainly have enough fodder to keep talking all night.
Top 20 Questions to Ask a Guy
Do you need a few questions to ask a guy to ensure you have a fulfilling conversation? Use this list of 20 good questions to ask a guy to keep your conversation fresh.
1. What do you look for in a girl?
Find out if he’s more into looks or personality. Or perhaps something else entirely!
2. Do you have any family traditions?
Asking him about family traditions will open up an entire world of conversation topics. You can learn more about his family, beliefs, and what to expect from him at certain times of the year.
3. If you fall for someone do you wait to say so until it feels socially appropriate, or do you just spill your guts?
Will he be the first one to say it or will you have to take the reins? This is also a good question to ask so you know not to overthink your situation with him.
4. What’s the most trouble you’ve ever gotten in with your parents?
Is he a bad boy or are his parents just strict? This is also another chance to find out more about his family without asking a more straightforward question.
5. Have you ever done anything illegal?
So, has he ever broken any laws? Maybe he never got in trouble at home because he’s never been caught.
Then again, maybe the answer to this question is his reason for getting in trouble at home.
6. What were you like in school?
Was he the class clown, jock, nerd, or just your average guy? This is your chance to learn more about a side of him you never met. Would the two of you hit it off if you met as classmates years ago? It’s definitely interesting to think about.
7. What’s your least favorite food?
You seriously don’t want him to suffer through a dinner full of food he hates or that he is allergic to. Try to ask him early on about any food aversions he has.
8. Would you wait for me to watch the next episode of a TV show we started together?
Is it about watching the show or watching the show with you? This is a fun question to ask because although you want his answer to be, “of course I’ll wait for you,” it also isn’t a big deal if he skips ahead.
9. What’s the next goal, big or small, that you want to accomplish in life?
Setting goals for yourself is an important step towards mastering self-control and persevering in life.
Whether big or small, the goals he sets for himself show he is staying motivated and is open to improving himself throughout life.
10. Is it unattractive to you if the girl you’re seeing makes a drastic physical change, such as hair color or cut?
If you’re prone to spontaneous, drastic, changes in appearance, then you should find out where he stands on the topic. This way you can give him a heads up before you alter your image.
11. What’s a topic you can never shut up about?
Listening to someone go on and on about their passions can be quite endearing. It’s always nice to know what excites someone.
12. Would you ever change career paths or do you see yourself having your current job until retirement?
Being content with your career is nice but there’s nothing wrong with wanting some change either. Find out how willing he is to follow his heart.
13. Is the idea of a spontaneous date interesting to you?
Does the man need a plan? Is he put off by the idea of going wherever the wind takes you? Spontaneity is exciting for some people but for others, it’s another word for anxiety.
14. Have you ever bullied someone or has someone bullied you before?
The playground can be ruthless. Was he the one leading the charge against the “nerds,” or was he the kid getting ridiculed?
15. If you could see any artist or band, alive or dead, in concert who would it be?
Want to find out more about his taste in music? This is a much better question to ask than, “what music do you like?”
16. Sweet, salty, or both at once?
You’re going to want to know what his favorite foods are for sure. But what about introducing him to new foods or surprising him? If you want to go the creative route you should first learn what entices his palate.
17. When it comes to libations, are you more of a beer, wine, or liquor kind of guy?
His answer to this question is good to know before making a reservation at a brewery or wine bar. Find out what he likes to drink, or if he even drinks at all.
18. If you could turn your hobby into a job, would you? Or would you keep it as your hobby?
A lot of people have side hustles. It’s a great way to earn a little extra cash while doing something you love. But sometimes that hobby or pastime loses its luster when it becomes your job.
Asking him about his hobbies as a career path is a good way to know if you should motivate him to do more or just let him enjoy himself.
19. What’s something you despise that is loved by everyone else around you? Conversely what is something you love that everyone else seems to hate?
How much does he stick out in his social circle? This is a spin on asking about his pet peeves. Asking this question will give you a better idea about his quirks.
20. Are you a cat person or a dog person?
Is man’s best friend his worst enemy? Pets are a big part of some people’s lives. If either of you have a pet now or ever want one, it’s a good idea to find out how the other feels.
10 Flirty Questions to Ask a Guy
Some people are natural flirts. Others can overthink it to the point they just tap out. If you’re wanting to flirt but are unsure how to make your intentions obvious, ask your guy questions that will keep him blushing.
1. What did you first notice about me?
Was it your eyes? Your confidence? What made him want to reach out to you?
2. So, have you told your friends about us?
You can gauge how serious he’s getting by whether or not he’s told his friends about you yet. Of course, if he hasn’t, just give it time. Maybe he’s taking things slow.
3. How do you flirt?
We all flirt differently. What is his go to strategy? Does it work for him?
4. Are you a show-off when you like a girl or do you play it cool?
Is he a quiet mysterious type or does he go all out to get a girl’s attention? Asking him how he acts when he likes someone will help you know if you’re the one he’s after.
5. Do you think about me when you’re alone?
Put him on the spot and find out if he stays distracted by you even when you aren’t around.
6. Have you been working out?
He just looks so strong. He must be working out, right?
7. Do you like it when a girl makes the first move?
Is he old fashioned or does he like a confident girl with drive?
8. Were you nervous when you first talked to me?
Harmless teasing is a great way to flirt. So, ask him if you make him nervous and put the pressure on him a little more.
9. What’s your favorite kind of date?
Does he like romantic dinners, casual movie dates, or something more exciting? If he hasn’t asked you out yet this question makes for a great segue.
10. When can I see you again?
Don’t wait by the phone for a text from him. If you want to see him again ask him when he’s available.
20 Dirty Questions to Ask a Guy
Want to spice up the conversation? Ask questions that will leave the guy you’re interested in wanting more.
1. What’s your most vanilla turn-on?
Sometimes what gets us in the mood is part of the set standard. Think risqué clothing, sensual touching, the typical stuff.
However, some vanilla sexual interests go beyond the standard simple turn on. Do glasses make him go crazy over a girl? Does he have a soft spot for a woman who knows her way around a car’s engine? Find out what unexpectedly gets him going.
2. What’s your kinkiest turn-on?
On one end of the spectrum you have vanilla sex, on the other is kinky. Getting down and dirty in kink isn’t for everyone and that is perfectly fine. But it is always good to know what works for a potential sexual partner.
3. What’s the dirtiest thing you’ve tried during sex?
Find out how adventurous he is during sex. Did he enjoy his sexual experimentation or was it a one time experience?
4. When did you lose your virginity?
Did he wait until he met that perfect person or did he lose his v-card as fast as possible?
5. How do you feel about PDA?
Is this guy really handsy? Do you mind? It’s important to find out if he’s as into public displays of affections as you are, or aren’t.
6. Are you more into giving or receiving?
Ask about how generous he is in bed. Does he enjoy giving pleasure or receiving more?
7. How long do you usually wait before you sleep with a girl?
Does he wait until the third date or is he okay with a casual hook up? Ask him if he has any set time frames for sleeping with someone so you know what to expect from him as a potential partner.
8. Do you watch porn?
Although people will try to deny it and some say it’s a terrible act, there is a lot of porn consumed each and every day. Find out if he takes a few minutes out of his day to look at or watch porn. If you’re feeling adventurous you could even ask him to watch it with you.
9. Do you have any fantasies we can play out together?
Wanna find out if he has a sexual bucket list? Ask him about his fantasies and see if he wants to try anything out with you.
10. What’s the farthest you’ve traveled for a hook-up?
Asking him this question is a good way to know if distance is a deterrent for him.
11. Have you ever sent a “you up” text?
The infamous booty call. We’ve all been there, at one end or another. Ask away and find out if he’s sent any hopeful late night texts.
12. Do you ever send nudes to girls?
How does he feel about sexting? Will he send a dirty picture over text if asked?
13. How do you feel about dirty talk?
Some people have no problem getting into character and dirty talking. Others find it too embarrassing to do with a straight face.
14. Is that a pistol in your pocket or are you just glad to see me?
Mae West made this line famous in the 1930s and it still holds up today. Repeating this suggestive quote will certainly get an interesting response from any guy you ask.
15. Lights on or off?
Mood lighting can really set the stage for a romantic evening. But when it boils down to the big event, does he keep the lights on or turn them off?
16. Have you ever been in a friends with benefits situation?
Sex is just sex to some people. It’s simply an exciting activity to pass the time. Having a friend with benefits isn’t a negative thing. Think of it as a level of maturity. He’s able to put aside emotional attachment and jealousy.
17. Has anyone ever walked in on you “in the moment?”
Want to see him blush? Ask if anyone has ever walked in on him.
18. Is it more fun in the morning, afternoon, or night?
Does he enjoy a little afternoon delight, or does he wait until bedtime to get frisky? Maybe he breaks up his morning routine with some excitement every now and then.
19. What number of past sexual partners do you consider too many?
Numbers matter to some people. Ask him what he considers to be too many sexual partners so you can learn more about what he would think of you and your history.
20. Are you going to ask me inside/upstairs?
As Elaine Benes from Seinfeld found out in an episode titled “The Label Maker,” asking to go upstairs implies you’re looking to have some adult fun.
If the night is ending too soon for your liking, be bold and ask him if he’s going to ask you inside his place. Or if you’re looking for even bolder questions to ask a guy, be straightforward and ask him to come back to your place.
20 Deep Questions to Ask a Guy
If you want to really get to know a guy, ask deep questions. You’ll learn more about why he is the way he is.
1. Who do you admire most in life?
It’s important to know who he looks up to in life. His answer can reveal a lot about who he aspires to be. Is it a family member or someone famous? What’s his reason for admiring them?
2. Are you receptive to new ideas and viewpoints?
A person that can listen to other peoples ideas and opinions without becoming angry shows a high level of emotional maturity. Find out if he is open to new viewpoints and changing old opinions in light of new information.
3. What made you choose your career path?
Did he stumble upon his current job or is it his dream career path?
4. Are you passionate about politics or do you prefer to avoid political discussions?
Before you dive into a conversation about a sensitive topic such as politics you might want to ask how he feels about the topic. Unless you’re ready for a debate, tread lightly when discussing political matters until you know if it’s his cup of tea.
5. Has anyone ever broken your heart?
Breakups can be difficult. Having your heart broken can forever change you. Ask him more about his past love interests to know if he’s been hurt before.
6. Have you ever broken someone else’s heart?
Has he ever had to break things off with someone and consequently left them feeling heart broken? How did he end things?
7. If you knew the world was going to end in a week, what would you do? Would you tell anyone else?
How would he react to a heavy burden like knowing the world is going to end?
8. What do you want to be remembered for after you die?
Does he want to leave a big legacy or does he simply want to be known as a good man?
9. If you could choose to have anyone else’s life, would you? Who would you want to become?
People say that the grass is always greener. But how do you know unless you walk in their shoes?
10. What is something you try to do to make the world a better place?
How does he help make a better world? Does he pick up litter, recycle, or volunteer at a shelter? Maybe you can plan a date to give back to society together.
11. What does emotional maturity mean to you?
Your definition of emotional maturity might differ from his. Find out what he considers maturity by asking him directly.
12. Do you believe in a higher power?
Religion, like politics, is a sensitive topic for some. It’s good to know where people stand to avoid offending their beliefs.
13. Would you alter your own past if you had the ability to do so?
He can change his past but everything else would change too. How would he handle the chaos effect on his own life?
14. Are you more of a free spirit or do you appreciate a strict schedule?
Does he need a plan? Or does he just go with the flow?
15. What’s something that always makes you angry?
Asking about what makes him angry is a smart move if you want to avoid seeing him express his rage.
16. Is having a job a means to survive or something to be passionate about?
Is his job just a job or does he live to work?
17. Should men and women have different roles in a relationship or should it be based on individual strengths and weaknesses?
Find out where his thoughts lie in regards to gender roles. Does he think women belong in the kitchen or does he want to see some glass ceiling shatter?
18. What do you expect from a relationship?
Is he looking for a lifelong commitment or some fun? What does a relationship mean to him and what does he expect from you if you start dating?
19. Have you ever been in love?
Loving someone and being in love is different. Being in love is a unique feeling and when it happens you just know. Has he ever fallen for someone?
20. What does being a good man mean to you?
This question will be sure to get him thinking. Does he try to be the best man he can be?
10 More Good Questions to Ask a Guy
Keep him on his toes with random questions that can pertain to any guy.
1. What’s your idea of the best day ever?
Does his idea of the best day involve highly organized plans? Or is he more interested in lounging around?
2. What’s the most dangerous experience you’ve ever had?
Find out if you’re dating a daredevil. Or maybe he’s just accident prone without the thrill seeking.
3. Planes, trains, or automobiles? How do you prefer to travel?
If you ever plan to travel together you’ll want to ask him his favorite mode of transportation.
4. How much time do you spend getting ready in the morning?
For women, rolling out of bed and hitting the road isn’t an option. However, men are often able to avoid spending too much time putting themselves together each morning.
Ask about his morning routine. You’ll get a better read on how much pride he takes in himself and how motivated he is.
5. What’s something kids today have you wish you had growing up?
We’re living through a technological boom and the advancements just keep on coming. Today, kids have access to wonders only seen in sci-fi movies 30 years ago.
Does he wish he could experience life as a child with an iPad or is he perfectly content with his childhood sans Wi-Fi.
6. Android or Apple?
How compatible are your phones operating systems? It isn’t a travesty if he has a different phone aesthetic than you do. There’s really just a difference in code.
7. What’s your favorite travel destination?
Where has he been that he could go back time and time again? Maybe he can take you one day and show you around.
8. What about a dream travel destination?
Do you two share some bucket list travel destinations? Get a good idea of his adventurous side by asking him what parts of the world he desperately wants to see.
9. Where is a place you never want to visit?
There are places in the world that are just off limits to some people. Find out where he draws the line with travel.
10. When was the last time you got genuinely frightened?
Encourage him to let his guard down with you and own up to a time he was recently scared.
20 Funny Questions to Ask a Guy
Whether you’re just starting to get to know someone or have been hanging out for awhile you’ll want things to be fun. Stick with more lighthearted questions to ask a guy to keep the conversation on a positive note.
1. What’s the cheesiest line you’ve ever used that actually worked on a girl?
When it comes to pick-up lines, the worse they are the better. Has he ever successfully used any cheesy lines to score a date?
2. Have you ever been asked to leave a public place?
If the answer to this question is yes, then there must be a pretty good story to go along with it.
3. What is your best corny joke?
Just like with pick-up lines, the best jokes are sometimes terrible. Does he have a go-to dad joke that makes you roll your eyes and hate yourself for laughing?
4. If you could be transported into any film franchise which one would you choose?
This is a great way to find out what types of movies he enjoys. It’s a creative break from the typical, “what’s your favorite movie” question.
5. Which direction do you hang toilet paper?
A long standing debate that genuinely matters to some people. Does he hang it up or down?
6. If you could choose a superpower, what power would you want?
Would he choose the ability to fly or something a little more specific to him. See how creative and imaginative he can be.
7. Do you sing in the shower?
If he does sing in the shower his facial expression will probably give him away before he answers your question.
8. What’s the worst thing you’ve done on a dare?
What horrors has he been subjected to during a game of truth or dare?
9. If someone asked to see your most recent Google search history would you be able to show them without embarrassment?
The thought of anyone looking through your internet search history is the stuff of modern day nightmares for many. Could he show his search history off without cringing?
10. Have you ever had 15 minutes of fame?
Find out if you’re talking to a celebrity or not. Find out what propelled him to stardom and what happened to end his success.
11. What’s your least favorite cliché job interview question?
Job interviews often seem to read from the same list of questions. What are the questions that leave him stumped or wishing he never had to answer.
12. Would you be willing to babysit your younger self?
So, was he a bad kid? Could he handle taking care of a little version of himself?
13. What movie do you think is better than the book it’s based on?
It’s often said that the book is better than the movie version. However, that’s not always the case. Find out if there is a movie he prefers over it’s book counterpart.
14. If we went on a crime spree together, what crimes would we commit?
Would you two be a modern day version of Bonnie and Clyde? Brainstorm your rebellious love affair together.
15. Were you ever a prankster? What kind of pranks have you pulled?
Does he enjoy pulling pranks on people? When he was younger did he drive his parents or teachers crazy? His answer will help you know if you need to be on the lookout for any of his practical jokes.
16. Do you ever find yourself yelling at your GPS?
It’s an inanimate object but it’s easy to get frustrated at your mobile GPS. If there’s ever a robot takeover, will he be punished for his treatment of his maps app?
17. What’s the riskiest style choice you’ve made in the past?
Does he have a blundersome past wardrobe? What’s the most ridiculous risk he’s taken with his fashion choices?
18. What’s your favorite curse word?
Is his favorite curse word something tame or unusual? How liberally does he use his favorite offensive words?
19. What do you think we’d be doing right now if the internet was never invented?
How would your lives be different? Would you even be talking or did you meet because of the internet? It’s entertaining to imagine our world without the technology we’re so accustomed to.
20. What’s something classy if you’re rich but trashy if you’re poor?
When you have money you can get away with a lot in life. Sometimes what people consider a social faux pas is perfectly acceptable if you have wealth attached to your name.
20 Personal Questions to Ask a Guy
Get to know the guy you like on a more intimate level by asking him personal questions.
1. Are you still close to an ex girlfriend?
There’s nothing wrong with remaining friends with an ex. But it’s always good to know if someone you’re dating is or isn’t friendly with their ex partner. It could simply mean he’s a decent person who sees his ex as a person, not just a person he dated.
2. Have you ever had a falling out with a friend? Can I ask what happened?
Losing a friend can be more difficult than a breakup. We consider the possibility of a breakup but the same thoughts are uncommon for friendships until it happens.
3. How often do you see your family?
If he really close to his family? Does he make an effort to see them frequently or do they live in a different area?
4. Do you ever want to get married?
Does the topic of marriage make him squirm or does he know what he wants from a relationship?
5. Which of your physical features are you most proud of?
Don’t forget to tell him you also love his favorite physical feature.
6. Who was your first kiss?
Was it a playground crush or his first love?
7. What’s your opinion on cheating? Does it ruin everything or can people bounce back?
Cheating is a deal breaker for most people. But is it something he can overlook if he cares enough about someone?
8. Have you ever had a girlfriend come between you and your friend group?
Find out if he’s ever had a girl Yoko Ono his friend group.
9. If you were going to let a girl down easy, what would you say to her?
How compassionate can he be when he knows he’s going to hurt someone?
10. Have you ever ghosted a girl and why?
Ghosting, left on read, whatever you refer to it as, this 21st century response to disinterest is on the rise. Has he ever just stopped responding to a girl he dated? How did that go over for him?
11. What was the last song or movie that made you emotional?
Learn more about his sensitive side. It really helps to humanize a person when they admit to being emotional.
12. Do you have any difficulties expressing your emotions?
He might be able to admit to getting emotional over a sad song or movie but what about other times? Can he easily talk about his feelings?
13. What’s your favorite way to relax after a hard day?
How does he like to decompress? A stiff drink, massage, or does he need time alone to be with his thoughts?
14. What’s something you’ve never told your family about?
Secrets can be necessary sometimes. Especially with family. Having boundaries with family members is a good thing. But you aren’t family. So, what has he kept from them?
15. Have you ever dated a friend’s ex?
Do him and his friends have a “bro code,” or are they free to date amongst the groups ex girlfriends?
16. What are some non negotiable boundaries you have?
It’s extremely important you find out where he draws the line in relationships. Ask him what his boundaries are so you never cross them.
17. What accomplishment are you most proud of?
Has he ever won any awards or accolades? What has he done in life that he’s most proud of?
18. What’s your biggest fear?
Clowns? Spiders? Failure? There’s a lot to be afraid of in the world. What is sure to frighten him?
19. How important is autonomy in your relationships?
Does he value his own personal sense of identity and desire his partner to have her own as well? When two people lose themselves in a relationship, it’s easy to lose sight of yourself. Having a sense of autonomy is healthy.
20. Have you ever told a small lie that spiraled out of control?
What’s his experience with a out of control white lie? Has his attempt to help a situation by not being completely honest backfired on him in the past?
How to Know That You’re Asking the Right Questions
As you have a conversation, if the flow feels natural you’re on the right path. The questions you ask a guy should allow for more than a simple yes or no. At the very least you should be able to ask him to expand on his response. Plus you’ll always be able to answer the question yourself.
Remember that getting to know someone takes time. So, utilize a few of these questions at a time and try to let a natural conversation occur. You can always come back and look over the list as you move forward to get more tips.