Let me guess.
You have a guy you like and you would like to know more about him.
But you’re stuck.
There are so many questions you could ask him, it’s hard to know where to get started.
Not to mention that dreadful feeling when you realize you’ve run out of things to say.
Luckily, I’ve got you covered.
Whether you want to know some great questions to get to know the guy you like, or you’d just like to keep the conversation going with some fun and silly questions, you’ll find it in this list.
Before we begin, just a quick note:
You’ll notice that most of these questions are open-ended questions.
That means they can’t be answered with a simple Yes or No.
This means that with just a handful of questions, you can keep the conversation going for hours.
Pretty cool, right?
Ok, with that out of the way, let’s get started with 200+ best questions to ask a guy you like.
16 Funny Questions To Ask A Guy
Like Charlie Chaplin said, a day without humor is a day wasted.
Now, these questions are important for two reasons.
First, you’ll get to show off your funny side – which is always a good thing. (Hint: men love women who can make them laugh)
Second, and more importantly, you’ll be able to gauge his sense of humor. If all of his answers are boring and bland, you might want to consider calling it a night.
After all, you don’t want to date a bore, right?
Here are the questions:
1. What would you do if you could be invisible for an entire day?
2. Have you ever put on makeup?
3. What was the most embarrassing moment of your life?
4. What was the funniest dream you ever had?
5. What was your most awkward sexual moment?
6. What’s your favorite comedy movie?
7. What’s your favorite pickup line?
8. Can you do any accents? (Show me.)
9. What was the funniest thing you ever did?
10. If you could be a woman for a day, what would you do?
11. What’s the lamest joke you ever heard?
12. What’s the weirdest nickname you ever had?
13. What’s your favorite joke?
14. Have you ever been caught naked by someone?
15. How many selfies do you take a day?
16. What’s the worst date you’ve ever been on?
17 Personal Questions To Ask A Guy
The questions below are designed to let you peel off the outer layers of his personality and to truly find out who he is.
For example, question #5 will tell you how adventurous he is, and question #9 will reveal to you his inner convictions.
Pick and choose the questions that sound most interesting to you.
1. What did you want to be when you grew up?
2. If you could change anything about your life right now, what would you change?
3. What’s at the top of your bucket list?
4. What are you most afraid of?
5. What’s the most adventurous thing you ever did in your life?
6. What was the biggest mistake of your life?
7. Do you have many acquaintances or just a few close friends?
8. How would you describe your perfect home?
9. What’s something about you that you wish more people knew?
10. What are your 3 best qualities?
11. What is the most expensive thing you ever bought?
12. What is your idea of a perfect vacation?
13. What would you do if you won the lottery?
14. What are some controversial opinions you have?
15. What’s the most spontaneous thing you’ve ever done?
16. What is the biggest personal change you’ve made in your life?
17. What makes you really mad?
15 Interesting Questions To Ask A Guy
These questions are great to use to eliminate those awkward silences that happen when you hit a bump in the conversation and don’t know what to say or ask next.
Each one of these could start a conversation that lasts for at least 30 minutes, so enjoy yourself.
1. If you’re trapped on a desert island and could only carry 5 items with you, what would they be?
2. If you could travel anywhere in the world, where would you go and why?
3. What’s your idea of a perfect day?
4. Would you rather be smart or happy? Why?
5. What foreign language would you like to be fluent in? Why?
6. What’s your strangest habit?
7. What is the biggest lie you ever told?
8. How do you spend your free time?
9. Have you ever been arrested? What for?
10. What is your dream tattoo?
11. What is your worst trait?
12. If you could have dinner with any person in history, who would you choose? Why?
13. What would you do in a zombie apocalypse situation?
14. Who inspires you the most and why?
15. What would a mirror opposite of yourself be like?
16 Questions To Get To Know A Guy
So there’s this guy you like, but you don’t know much about him.
Maybe it’s your first date, or maybe you’re spending time at work or at the gym and you’d like to get to know him a bit more.
Arm yourself with these questions and he’ll be an open book to you.
1. If money wasn’t an issue, where would you live?
2. What is your dream job?
3. Are you more introverted or extroverted?
4. What hobbies do you have?
5. What’s your favorite meal?
6. Where did you grow up?
7. What was your favorite subject in school? Why?
8. Do you think it’s better to ask for permission or forgiveness?
9. Would you rather live in the suburbs or in the city? Why?
10. What is your favorite childhood memory?
11. If you didn’t have to sleep, what would you do with the extra time?
12. What annoys you the most about other people?
13. Are you usually early or usually late?
14. What is the most impressive thing you know how to do?
15. How do you unwind after a stressful day?
16. How do you deal with people in your life you don’t like?
15 Cute Questions To Ask A Guy
His answers to these questions will, in all likelihood, make you go “Aww” … and that’s a good thing.
The truth is, these kinds of adorable questions and answers will bring you guys closer together, so don’t be afraid to ask.
Oh, and one other thing: Most guys will feel silly and awkward when answering these questions, so be sure to encourage him and make him comfortable. One great way to do that is to start by sharing your experience first, then asking him to do the same.
1. What qualities do you find most attractive in a woman?
2. Do you like kissing in public?
3. When did you first kiss a girl?
4. Did you ever have a crush on your teacher?
5. Are you a dog person or a cat person?
6. What were you like as a kid?
7. If you could become any animal in the world, which one would you choose? Why?
8. What are some quirks you have that most other people don’t?
9. What is the luckiest thing that has ever happened to you?
10. Who was your first crush?
11. Has a movie ever made you cry?
12. What’s something that can always make you smile?
13. If you could describe me in just three words, what would they be?
14. What is your favorite way to spend a rainy day?
15. What’s the nicest thing you’ve ever done for a girl?
14 Questions To Ask A Guy You Just Met
If you just met a guy you would like to get to know better, read on.
It doesn’t matter if you met in a bar, on the street, or even online.
The questions below will make him open up to you.
Here are the 14 best questions to get to know a guy:
1. What’s the first thing you’ve noticed about me?
2. What are you passionate about?
3. Do you like it when a girl makes the first move?
4. What’s the worst job you ever had?
5. How would your friends describe you?
6. What’s your favorite cuisine?
7. Are you always this charming?
8. What happens on a regular “guys’ night out” with your friends?
9. What are you thinking about right now?
10. What is the one thing most people get wrong about you when they first meet you?
11. What do you think about or do when you’re alone?
12. Do you like it here? (if you just met in a bar or club)
13. What makes you happy?
14. What’s your dream car?
17 Relationship Questions To Ask A Guy
Let’s be honest:
Guys aren’t that great when it comes to opening up.
That’s doubly true when it comes to relationship questions.
This is why it’s up to you to be the first one to ask one of these questions.
Just take it easy: don’t ask too many of them in a row, otherwise, you’ll sound like you’re part of the Spanish Inquisition.
1. What was the longest relationship you ever had?
2. Do you stay friends with your exes?
3. Could you ever forgive cheating?
4. Have you ever cheated on your girlfriend?
5. What do you think about open relationships?
6. Why did you break up with your last girlfriend?
7. How would you describe your ideal relationship?
8. What is a relationship deal-breaker for you?
9. Why did your last relationship end?
10. Do you believe long-distance relationships can work?
11. What physical qualities of mine do you find most attractive?
12. What non-physical qualities of mine do you find most attractive?
13. What is your biggest weakness in a relationship?
14. What is your biggest strength in a relationship?
15. What is one behavior you never tolerate in a relationship?
16. What do you remember the most about our first date?
17. What do you think a relationship needs to be successful?
15 Deep Questions To Ask A Guy
Now, you definitely don’t want to ask any guy these questions.
These are very deep questions best reserved for a guy you want a relationship and a future with.
I personally recommend questions #6, #7, and #9 as some of the best deep questions to ask a guy you like.
1. How close are you to your family?
2. Are you religious?
3. Who is the most important person in your life?
4. How many children would you like to have? Boys or girls?
5. What are you most insecure about?
6. What are your highest moral values?
7. What do you think a wasted life looks like?
8. Who or what has been the biggest influence on you?
9. What would you do if you had only one year left to live?
10. Have you ever given to any charities? Which ones?
11. What is your earliest memory?
12. Do you make decisions with your heart or your head?
13. What is the one secret you haven’t told anyone else before?
14. Do you believe everything happens for a reason?
15. Who inspires you?
13 Romantic Questions To Ask A Guy
Is he a romantic or not? Use the following questions to find out.
If his idea of a romantic date is Netflix and chill, you might want to cut the date short.
Now, if he’s not exactly Prince Charming, don’t despair.
Contrary to popular belief, men can and are often willing to change for the women they love.
These questions will just allow you to test the waters.
1. What’s your idea of a romantic date?
2. What’s the most romantic thing you ever did?
3. How many times have you been in love?
4. What does love mean to you?
5. Do you believe in love at first sight?
6. Where’s your favorite place to be kissed?
7. What is your favorite way of showing affection?
8. What is your favorite way of receiving affection?
9. Do you believe in soul mates?
10. Valentine’s day – corny or not?
11. What is your idea of a perfect woman?
12. Do you like cuddling?
13. What is the longest time you’ve spent with your girlfriend?
19 Dirty Questions To Ask A Guy
Ok, let’s get kinky.
We both know that sex is extremely important in a relationship, right?
And we both know that these dirty, sexual questions do tend to bring out the best answers.
Not to mention the fact that you’ll find out whether you guys are sexually compatible or not.
Now, some of these are great to ask in person…others are best sent as a text.
Use your own judgment and feel free to add your own questions.
1. What is your biggest turn on?
2. What’s your kinkiest sexual fantasy?
3. Where is the weirdest place you had sex?
4. What’s your favorite sex position?
5. Did you ever use props in the bedroom? Which ones?
6. What’s your idea of good foreplay?
7. Did you ever become horny while texting?
8. What would you do to me if I was with you right now?
9. Do you like role play? Which roles are your favorite?
10. What’s something new you would like to try out in the bedroom?
11. What is your idea of a perfect blowjob?
12. Anal sex: yes, or no? Why?
13. What’s the dirtiest thing you’ve ever done with someone?
14. If you could only have one type of sex for the rest of your life, which one would you choose: oral, anal, or regular?
15. How long was the longest time you had sex without stopping?
16. Do you like rough sex or are you more gentle?
17. Have you ever had sex in public? Where?
18. Did you ever try BDSM? How did you like it?
19. Do you like experimenting with different positions?
16 Silly Questions To Ask A Guy
Guys love women who don’t take themselves too seriously.
If you ask any of the questions below, you’ll make both of you laugh and he’ll be instantly more attracted to you. (laughter is the best aphrodisiac)
1. What is your silliest pet peeve?
2. Are you a nice drunk or a mean drunk?
3. Would you like to be famous? Why?
4. What’s your favorite snack?
5. Would you ever visit a nude beach?
6. Do you like winter or summer better? Why?
7. What is something you’ve done you’ll NEVER do again?
8. What dumb accomplishment are you most proud of?
9. What’s the one thing you procrastinate on the most?
10. If you could write to your ten-year-old self, what would you tell him?
11. If you could have chosen your own name, what would you have chosen?
12. What is the longest you’ve gone without sleep?
13. What is the most useful thing you can teach me in 5 minutes?
14. What technology do you hope will be invented in your lifetime?
15. Do you sing in the shower? If so, what song?
16. What do you think about tattoos?
14 Questions To Ask A Guy Over Text
Some questions are better asked in person, while others are better asked over text.
When you ask him a question over text, he’ll have more time to think so you might get a more thoughtful answer.
1. What’s the weirdest text you ever received from a girl?
2. Can you describe yourself in a sentence?
3. What’s the best photo you’ve taken?
4. What’s the worse text you’ve accidentally sent?
5. What is the one gift you would like to get, but never do?
6. What’s your funniest online dating experience?
7. What’s the most ridiculous thing you’ve seen online recently?
8. Be honest…how many selfies do you have on your phone?
9. What are your biggest turn-offs in a relationship?
10. If you could have chosen your name, which one would you have chosen and why?
11. What is your favorite kind of art?
12. If you had an extra $100 to spend on yourself each week, what would you do?
13. What’s the most out-of-character decision you ever made?
14. Where and when do you get your best ideas?
15 Random Questions To Ask A Guy
Lastly, here are some fun questions that are just kind of…random.
If you hit an awkward pause in a conversation and can’t think of anything else to say, just throw one of these questions at him.
1. What’s your favorite book? Why?
2. Where is the most interesting place you’ve been?
3. What do you hope never changes?
4. What’s your favorite movie? Why?
5. Which of your scars has the best story behind it?
6. If you could have one superpower, which one would it be?
7. What do you think should be taught in school that isn’t already?
8. What is your signature dish?
9. What makes you feel alive?
10. What song defines your life?
11. Pets: yes or no? Why?
12. If you could be one of the first settlers on Mars, would you? Why?
13. Are you the only child in the family?
14. Do you like winter or summer better? Why?
15. What is your zodiac sign?
So there you have it – over 200 questions you can ask a guy to find out more about him and keep the conversation going.
Whew, that was a lot, wasn’t it?
I suggest you bookmark this page and write down a couple of questions you can ask your guy the next time you see him.
Then come back and get a few more.
Oh yeah, be prepared to be asked the same question you asked him. So you probably don’t want to ask a guy anything you’re not comfortable answering.
P.S. If you liked this article, you’ll love 1000 Questions For Couples from Michael Webb.
He’s an international relationships expert who was featured on Oprah and countless other shows.
In this book, he reveals the most important questions you can ask a guy to get him to fall in love with you and be yours forever.