Questions to Ask a Guy [Best Dirty, Funny, Interesting, Awkward, Flirty]


Here is an ultimate list of Questions to ask a guy in 2019.

Best part?

This list has various kinds of new questions like dirty, weird, flirty, interesting, funny, sweet, cute and deep much more.

Here we go:

Good true questions to ask a guy

1). One thing that you will never do again?

2). Would you prefer to be twice as smart or twice as happy?

3). What happened the last time you cried?

4). When was the last time you were very nervous about doing something?

5). What would surprise your parents about you?

6). What is your worst habit?

7). What super power would you like to have for a day?

8). What fictional character do you have a crush on?

9). One good thing that you truly like about me?

10). Do you have a strange habit?

11). Who knows you the best?

12). What did you do after school?

13). The last book that you read and absolutely loved?

14). The best TV show in the world?

15). So far, which has been your best year and why?

16). If you could go back in time, what would you change and why?

17). An experience that disappointed you deeply?

18). 2). Would you rather ask for forgiveness or permission?

19). Love or unlimited money?

20). If you came to know that you would die in a week, what all would you do?

21). Vacationing at a beach or a vacation in Europe?

22). If you had been a child prodigy, in which area would you have highlighted?

23). What is the one thing that you truly dislike about me?

24). With a celebrity life, would you change?

25). If you were a singer, what would you call your first album?

26). If there were only one condiment in the world, what would you like it to be?

27). How many people would you like to invite on a Friday night?

28). A strange thing that makes you break a relationship right away?

29). What fictional character reminds you of yourself?

30). Do you believe in Karma?

31). Your favourite TV program as a child?

32). Something strange that attracts you to a person?

33). Something that you are superstitious about?

34). Do you think that it is important to be aware of the news?

35). The best gift that you have ever received?

36). If you were told that you could gift someone with something and the budget is unlimited, what would you gift and to whom?

37). The kindest thing that anyone can say about you?

38). An enormous house in the suburbs or a smaller one with an excellent view?

Funny questions to ask a guy

1). Would you give one of your fingers in exchange for having free Wifi wherever you go for the rest of your life?

2). The first thing you would do if you had one day in the body of a woman?

3). What would you like throwing several times against a brick wall?

4). Tell me something that women should never do?

5) .Who would you hate to see naked?

6). When staying in a witness protection program, what would your nickname be?

7). What would you be willing to do for a million euros?

8). Why do you think they use sterilized needles to give a lethal injection?

9). If all rights are reserved, then what about the left?

10). How often do you bathe?

11). Are you one of those people who pretend to know everything online but still rely on Google?

12). Do you like stuffed animals?

13). Has anyone ever congratulated you after sex?

14). Do you ever wonder about the sex life of a cartoon?

15). Have you ever suffered an injury due to sex?

16). Have you ever been walked on when you were naked?

17). What would your favorite joke be?

18). If you could date a man for a day, who would he be?

19). Have you ever walked on someone naked?

20). What do you think is your worst physical attribute?

Dirty questions to ask a guy

1). How do you like to relax?

2). What are you wearing right now?

3). Do you admire yourself naked in the mirror when you’re about to bathe?

4). Have you had wet dreams ever?

5). Which song is ideal according to you to have sex to?

6). What was the craziest porn movie you watched?

7). Do you collect something like a trophy from the people you have sex with?

8). Something that is your fetish when it comes to sex?

9). Something that you have a phobia about when it comes to sex?

10). A phrase or a word that you often say when you have sex?

11). Do you sleep after sex?

12). Do you smoke after sex?

13). Do you ever go to a sex shop for shopping?

14). What is your favourite colour for underwear?

15). What sexual activity do you think you excel at?

16). What is the maximum amount of time you’ve had sex without stopping?

17). Have you ever participated in a threesome with someone of the same sex?

18). Have you ever participated in a threesome with a friend?

19). Craziest place you’ve had sex?

20). A place where you like to be kissed?

21). Would you like to make love in front of other people?

22). Have you ever practiced cyber sex?

22). Before we started out, did you ever fantasize about me or look at me when I was not looking? *You have always wanted to know how badly he wanted to connect with you, right?*If I were to wear a sexy outfit, which character would you want me to dress as?

23). What do you think should be our next step to make our sex life more exciting? *If your sex life is starting to get predictable, this is a great way to get your boyfriend to talk about the new things that he would like to try in bed without feeling uncomfortable.*

24). If you were with me now, if you could do anything for me at this time, what would you do?

25). If we were just friends and I got drunk with you, would you take advantage of me? *There is a good chance that just this question will make him sexually excited.*

26). You like me when I’m shy and sexy; or daring and sexy? *Some guys like their girl is dominating in bed and is in control, while most boys love it when they’re kissing a girl who is more timid and shy in bed*

27). Tell about the sexiest dream you’ve ever had about me. *Conversations like these make for fun sexual conversations while spending time with the other. It is also a great way to get your guy to talk about their sexual fantasies while using his dream as an excuse.*

28). If we were having sex on a holiday and you realize that someone is watching us from the next room, would you stop having sex or continue having sex? *Discover how wild and mischievous your boyfriend is when he is hot.*

29). If I ever surprised you when you were masturbating while thinking about me, would you be embarrassed by it? *Let’s face it, just because you are not having sex with your boyfriend, he will not stop masturbating. Instead of making a fuss about it or confronting him about it, talk about this in a light-hearted atmosphere.

30). Before we met, what was the sexiest thing that you ever did to someone else? *Most of the guys walk on tiptoes about their past, even if their girlfriend is very curious about it. Use this question to know how sexually adventurous your boyfriend is.*

31). If you could have a threesome with another girl and me, who would be you choose? *This question will help him to see that you are a true Wildcat and are not so shy and timid as you pretend to be on the outside.*

32). What kind of vacation would you prefer: A romantic mountain where we can be locked in our room all day or a destination or beach party where we can grind and make out while having fun and dancing in the nightclubs?

33). Tell me a secret sexual fantasy of yours that you want to try with me.

34). Do you think of any girl who has a little crush on you right now? *This question will boost his ego and help him to open up to you about his own personal life beyond your relationship.*

35). If you ever play truth or dare with another couple, do you think you would do something evil in them?

36). What do you think is the sexiest part of my body? *Once you know this, all you have to do is use that part of your body to wake your boy up and when the lights are off.*

37). Who do you prefer, a girl with a beautiful face and a medium body, or a child with a normal face and a stunning body?

38). If you had to kiss a girl anywhere in the body except the face, which part would you first kiss?

39). If you accidentally saw a naked girl and she did not know that you’re looking, you would look away, or you would continue to see her?

40). Do you like talking dirty during sex? *Most men and women who enjoy talking dirty are too embarrassed to reveal this secret to anyone. And the easiest way to get him to open up is to ask him about it when you do not feel the pressure of being judged about it.

Awkward questions to ask a guy

Here for you now are some awkward and uncomfortable questions to ask a guy. (Devil laugh)

1). Do you like me?

2). Are you gay?

3). Do you really want us to have sex?

4). What do you feel for me?

5). Why do you want me to stay with you?

6). Are you going to call me tomorrow?

7). Are you a virgin?

8). Are you rich?

9). How much do you earn?

10). Have you ever had a sexually transmitted disease?

11). Do you love me?

12). Have you ever kissed another man?

13). Are you bisexual?

14). Would you hold me please?

15). Have you had your first kiss yet?

16). Do you masturbate?

17). How many women have you been with?

18). Which of my friends do you find the most attractive?

19). Would you like to have kids with me?

20). Why did you break up with your ex?Excuse me if these questions seem obscene but they are awkward and uncomfortable. Hence, they feature here.

Interesting questions to ask a guy

Now we have for you some interesting questions to ask a guy.

1). What movie deserves a sequel?

2). What is your favorite cereal?

3). Something that you always wanted as a kid but never had?

4). What is the nicest thing anyone has ever done for you?

5). If you could resurrect a famous tomb, who would you choose?

6). If you were at home on a rainy Sunday afternoon, which movie would you like to see?

7). What historical figure would you like to have a chat with?

8).What is the most inspiring movie you ever saw?

9). If you could get rid of an invention, what would it be?

10). If you could buy an object to complete your home, what would you buy?

11). Is there anything hanging in your room that motivates you?

12). What colour is your toothbrush?

13). Any movie that made you hot?

14). Have you ever had homosexual fantasies?

15). Have you ever had a voyeurism experience?

16). What kind of person do you consider yourself to be in bed?

17). Do you like having sex drugged or drunk?

18). Do you enjoy reading erotic stories?

19). Have you ever had sex in the water?

20). What is the first thing you look at in the opposite sex?

Flirty questions to ask a guy

Some flirty questions to ask a guy for all those women who are in the mood for some light and fun flirting. 😉

1). At what age did you fall in love for the first time?

2). What is the weirdest place you’ve ever had sex?

3). What is your favorite place to have sex?

4). Have you ever stripped in from of other people?

5). Have you ever left your home without underwear?

6). Have you ever clicked someone without clothes?

7). Something sexual that you would never do?

8). Do you have nude photos or porn videos in your computer?

9). Have you ever looked at someone in the street an gotten excited by it?

10). Have you ever seen some guy in the street with an erection?

11). For you, what is the definition of a perfect day?

12). What does friendship mean for you?

13). What was your first impression of me?

14). Just before kissing a girl for the first time, what did you think?

15). What is your favorite memory with me?

16). If you can ask me for three wishes, what would they be?

17). What were the first words that you and I ever exchanged?

18). How do you describe me in front of other people?

19). Who is the person that you most admire in your life?

20). Who helped you with your first date?

Best questions to ask a guy

Here for you now is a list of some of the best questions to ask a guy.

1). Do you have a place where you enjoy going to think?

2). What profession have you always admired?

3). What is your first love?

4). Would you like to get married someday?

5). Where would you like to go on a honeymoon?

6). What most excites you in a woman?

7). What country would you like to live in?

8). Do you believe that there is life on other planets?

9). What is your worst nightmare?

10). What is your most recurring dream?

11). What according to you, is the definition of a perfect date?

12). Do you ever rehearse what you have to say before making a call to someone?

13). Do you have a feeling about how you are going to die?

14). What are you most thankful for in life?

15). What is the greatest achievement of your life?

16). What is your most precious memory?

17). What is your most terrible memory?

18). What does friendship mean to you?

18). When was the last time you cried in front of someone else?

20). What role does love play in your life?

Good truth or dare questions to ask a guy

Some good truth and dare questions to ask a guy.

1). Name ten body parts of your partner that you like to kiss.

2). What was the most embarrassing moment of your life?

3). Have you ever been humiliated?

4). Describe the quality or feature that you would like to change about yourself.

5). Have you ever fallen in live with the friend of your partner?

6). What is the evilest thing you have ever done in your life?

7). If there was no one here right now, would you make love to me?

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8). What is the worst rumour or gossip you said or repeated and realized at the end that it was something false?

9). What is your wildest fantasy?

10). Have you ever peed in a pool?

11). Have you ever kissed someone of the same sex?

12). If you had to choose personally someone you know for a threesome, who would it be?

13). From the people who are playing this game, who do you think has the best body?

14). Have you ever masturbated?

15). At what age did you start masturbating?

16). Has anyone ever caught you masturbating?

17). Have you ever masturbated in a public place? Where?

18). Have you ever masturbated in from of anyone? Who?

19). How often do you masturbate?

20). Have you ever masturbated while thinking of someone other than your partner?

Embarrassing questions to ask a guy

Some embarrassing questions to ask a guy.

1). Have you ever had sex in your parent’s house?

2). Have you ever been flatulent in front of your girlfriend?

3). Have you ever stolen something from the supermarket?

4). Have you ever fallen in love with a girl minor in age?

5). Have you ever used cream or chocolate to spread over the body of someone?

6). Have you ever fooled around with a friend, sexually speaking?

7). Has your mom ever caught you watching porn?

8). Have you ever been caught having sex by anyone?

9). What is your biggest sexual fantasy and who do you want to fulfil it with?

10). How would you introduce your boyfriend to your dad?

11). Have you ever masturbated with some friend or cousin of yours?

12). What is the craziest thing you have done, sexually speaking?

13). Do you sing in the shower?

14). What is your preference in underwear?

15). Are you too much of a guy for any girl?

16). Have you ever kissed another man?

17). Are you afraid to be alone at home?

18). Do you cry a lot?

19). Do you hide your emotions in public?

20). Are you still in touch with the first woman you made love to?

Questions to Ask a Guy on a First Date

Here is the list of questions to ask a guy on a first date.

1). What are the things that you like and dislike?

2). What kind of movies do you like?

3). What are the places you like to visit again and again?

4). With whom do you feel most connected to in your family?

5). What kind of food you like the most?

Such kind of questions to ask a guy can work as a reminder for you to order wisely from the next date with him.

6). Tell me something about your family.

7). Do you like music? What is your favorite genre of music?

8). Which is that sportsperson who has always been your idol?

9). Who is your most favorite celebrity?

10). Do you like the job that you have right now?

These questions to ask a guy are simply to know his mindset about the job he is doing right now.

11). What time you like the most? Is it the day time or the night time?

12). If you ever have to buy a house then which location would you chooses for it?

13). Which is your favorite superhero and why?

14). Have you ever been seriously allergic to some kind of usual things?

15). Which one is your dream car?

These are just random questions to ask a guy to carry on the conversation with him so that you guys have at least something to talk.

16). Do you like watching movies? Which one is your favorite movie?

17). What would you like to choose between tea and coffee?

18). What kind of job would you like to do someday?

19). Which is your most favorite holiday destination?

20). Where do you want to see yourself in the upcoming time span of five years?

Such kind of questions to ask a guy are to know that what are his future plans and prospective about himself.

21). What would you do in a situation where your blind date is a completely insane girl?

22). Who are your favorite five people in this world and why?

23). which one is the most annoying person in your life with whom you are living forcefully?

24). Do you feel dominated by a girl who is way taller than you?

25). Who is the person that comes in your mind when you wake up in the morning?

Such questions to ask a guy are just to know that who counts the most in his life.

Questions to Ask a Guy You Want to Date

1). What are the five things or person in your life that makes your life worth living?

2). How do you think a relationship imposes limits in your life?

3). Have you ever been into an open relationship? How was the experience?

4). What are the insecurities you can never escape when you are in a relationship?

5). What is your first preference, a romantic date with your girl or a chill time with your close friends?

These types of questions to ask a guy would let you know his preference in his life that whether he wants to choose friends or his girl.

6). Have you ever harmed anyone out of your anger? What was the reason of this anger?

7). What was the longest duration for which you didn’t shower?

8). What is more important for you, winning an argument with your partner or losing the argument but winning her heart?

9). What is your biggest turn on point?

10). How much the cast and creed of a person matters for you?

Such kinds of questions to ask a guy are perfect to know his mindset about the rest of the people.

11). Have you ever talked to yourself while looking in the mirror?

12). How many girls have you dated before me?

13). What is the ultimate idea of yours to party hard?

14). What was the biggest amount that you have ever spent on a girl?

15). What is the biggest perk and biggest low of being in a relationship?

If you want to know that what he actually thinks about relationships then such questions to ask a guy are just perfect.

16). Is it okay for you that your wife is not a virgin?

17). What is that one game in which no one can defeat you?

18). What is your ultimate place to hide away from all the problems in the world?

19). What is the biggest fear or insecurity that you have in your life?

20). At what limit you can cheat someone until you get caught?

These types of questions to ask a guy are perfect to know him as a person and to know about his ethics of life.

21). Have you ever caught by your then current girlfriend cheating over her?

22). What do you think about a girl who is in an open relationship?

23). Whom do you trust the most in this world and why?

24). Describe yourself in just one word.

25). What is the best idea for you to celebrate your birthday?

Such questions to ask a guy can be really helpful for you to plan his birthday just the way he likes.

Important Questions to Ask a Guy before Marriage

Here I am presenting a list of most important questions to ask a  guy before marriage.

1). What was the longest duration for which you dated a girl before me?

2). What should a person do to get over his/her ex?

3). How does it feel like to be ditched by a girl according to you?

4). How many girlfriends you have had in the past? What was the reason of breaking up with each of them?

5). If you have to relocate because of your job and work then would you consider having a long distance relationship with me?

Such questions to ask a guy are really important because it can decide a lot about your marriage.

6). Do you like children? At what age you expect to have kids?

7). Have you ever been into a relationship where you got engaged but could not marry? What were the reasons of not marrying her?

8). What is the one thing that you learned about love from all your past relationships?

9). How serious you are about me?

10). What are your views about the long lasting marriages and their strengths?

Such questions to ask a guy is really important from the perspective that you are deciding to marry him anytime soon.

11). Are you happy with the earnings you are having right now?

12). Have you ever blamed your work or job for one of your break ups?

13). What is the importance of your family members in your life?

14). With whom do you find yourself the closest in all your family members?

15). Are you comfortable in letting me meet your family members?

These types of questions to ask a guy are really important as they determine a lot about his seriousness for you.

16.are you comfortable enough in having a partner who is more educated and well settled than you?

17). How looks and appearance plays a role for you to pick a girl for you out in a crowd?

18). Are you a person who can spend a lot on branded things?

19). Would you leave your girl because she cannot have children?

20). What is the role of your friends in making the decisions of your life?

Now this matters a lot. Such questions to ask a guy can reveal that how much space his friends have in his life.

21). If life puts you in a platform where you need to pick between your friends and your partner then whom do you choose and why?

22). If you will ever have a pet then what it would be?

23). How do you see a live in relationship?

24). How much money matters in your life?

25). If any of your friend is demanding a dowry from his bride then what would you do in this situation?

Such questions to ask a guy are must. They will tell you about the thinking of this guy about marriages and relationships.

Top 20 Questions to Ask a Guy You Really Like

1). In what age you got kissed for the first time?

2). Have you ever get attracted by some cougar?

3). What it is for you to visit a strip club with your pals?

4). Would you ever consider visiting a nude beach?

5). What is your ultimate idea of having the best night of your life with your partner?

Such questions to ask a guy can be a real turning point as it can greatly define the bond that you two are going to share.

6). What are your views about gay or lesbian relationships and marriages?

7). After a dispute between your mom and wife whom would you support and why?

8). How do you think you can instantly turn on a woman?

9). What do you like the most about a woman?

10). Which is that one habit that you can never give away for anything?

Such types of questions to ask a guy are just to know that what kind of habits are these he is obsessed with.

11). If you are going to have a rebirth then what do you want to become in the next birth?

12). If you could live with an x rated star then who it would be?

13). What is the main flaw of being a guy?

14). If you could marry a Disney princess then with whom would you like to get married?

15). What kind of books do you find the most engaging and interesting ones?

These questions to ask a guy are important as the taste of books can reveal a lot about the person.

16). If you have to name a person in just a fraction of second then who it will be?

17). What kind of a person you are? Are you more a thinker type of person or more of a doer without thinking much?

18). If you have to take three names with a certain alphabet (given by you) then what are things you would like to name?

19). What is the name of your music playlist?

20). What is the biggest disadvantage of growing up according to you?

These questions to ask a guy are just the random type questions.

21). Have you ever made your parents embarrassed in public as a kid?

22). If you have to arrange 1 million dollar in a day then how would you do it?

23). How would you relate yourself with the story of a movie?

24). What is the most amazing thing that has ever happened with you?

25). Would you rather be rich or be hated by everyone for entire life?


1). What three things do you appreciate most in a person?

2). If you could learn to do something new, what would you choose?

3).Which is the last book that you read?

4).If you could be an animal, what would you be?

5). How is your car’s trunk? 

6). Are you one of those who would sacrifice the life of one person to save a hundred?

7). What is it that you look for in a woman or according to you, who is the ideal woman for you?

8). Do you think you have any shortcomings? If yes, what are they? List a couple of them.

9). What would be your slogan?

10). What are the best and worst quality of your gender and that of the opposite?

11). What is the strangest object in your room?

So, you’ve reached the end of this article. Hope you got some real insight into the psyche of your boyfriend or your guy and know now what questions to ask a guy, should the opportunity present itself.

Keep visiting, will update latest questions to ask a guy soon. Hope you enjoyed this questions to ask a guy collection.

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Nagama Ansari
Nagama Ansari is a well-known blogger and digital marketer, working in the industry from several year, and has written more than 1000+ well-researched information guides and product testing review articles..