Tricky questions for a guy: 100 provocative questions

Are you easy to catch on to a question? Can you answer 100 misleading provocative questions? Tricky questions to the guy from this article will show how easy it is to confuse or catch him at his word. We tried to put together in this article a list of well-thought-out, most interesting tricky questions for guys about finances, work, family, friends, love, and relationships.

It is difficult to answer these questions with an unequivocal “yes” or “no” so as not to fall into the trap. For example, one of them: “Will you take your mother-in-law on vacation with your family”? How do you like this question? The rest of the list will also make you break your head.

So take a look at the questions below, which we updated in 2019, and choose the right ones for your boyfriend. Feel free to ask him to diversify your communication.

Why tricky questions are interesting to a guy

  1. Questions like these can make a conversation with a guy hilarious, making it more interesting than usual. This is a kind of master class on polishing knowledge about men. So we definitely recommend that girls have a list of these questions for their boyfriend in their arsenal of communication.
  2. The answers to these questions help to understand the difference between male and female nature. After all, guys avoid flaunting their inner world, and also rarely share their personal lives with others. That’s why girls need a tricky approach – thoughtful questions. Thanks to them, they will be able to penetrate the male “heart” and get an idea of ​​the character of their chosen one. (A list of questions you can ask a guy to get to know him better will also help).
  3. Tricky – these are questions with a trick, which are difficult to answer unambiguously. So the guy will have to use his brains to answer them. This will help the girl see his real, unfeigned character.
  4. Guys think they are smart enough not to fall for provocative questions. However, they fall for these tricks. Common sense and experience will not help here. When it comes to tricky tricks, some questions are funny, others are puns, and the answer to others sets a trap. Therefore, it would seem that the answers are logical or in accordance with common sense, but the thought that comes to mind is quite often wrong.

Men, like women, also use social networks. Therefore, they need strong words and phrases for status in them. We recommend reading men’s statuses for guys for all occasions.

Trick Guy Questions

  1. Can you lie without saying a word?
  2. If not now, then when?
  3. Do you persist in what you must yield?
  4. Is male crying a sign of weakness or strength?
  5. Would you break the law to save the one you love?
  6. Do you like what you have?
  7. When all is said and done, will you keep talking or will you start doing?
  8. If your brother spoke to you the way you speak to others, how long would your friendship with him last? (We recommend reading quotes and statuses about brothers with meaning in order to appreciate them even more)
  9. Time or money?
  10. Is it better to listen to the brain or the heart?
  11. Should there be a hierarchy in the family?
  12. Do you find older women attractive?
  13. Could marry an ugly woman, but rich?
  14. What are you looking for in a girl?
  15. Is it better for a girl to use a cool or cheeky social media status to get a guy’s attention? (We recommend reading 155 cool statuses for girls on Instagram and VK that get a lot of likes).

Provocative questions for a guy

  1. Are you deceiving others? How often, in what case?
  2. In a relationship, who should be in charge: a man or a woman?
  3. What would you do if you could be invisible or a woman for a whole day?
  4. What is the one thing you will definitely try to save if the house suddenly goes on fire?
  5. Which of your female friends do you most often compare yourself to?
  6. Having the opportunity to commit any crime with impunity, what will you do?
  7. What is better for a man: to be smart and ugly or mute, but beautiful?
  8. With the ability to lock up anyone in a psychiatric hospital, who would they lock up?
  9. What is most important for a girl to have: attractiveness, intelligence or beauty? And which one do you prefer?
  10. There are different opinions about how often a man and a woman should take a bath. What do you think?
  11. How often should a man and woman change their underwear or socks?
  12. Can you stand bad breath, sweat or dirty clothes? Should we talk about it if this happens?
  13. Does it annoy you if a person “burps” or “gases”?
  14. Have you ever had a mental disorder?
  15. Does this suit me…?
  16. Will you buy me…?
  17. Does a man like to receive gifts?
  18. Who is more important to you: mom or girlfriend? (We recommend reading 104 mom quotes that will help answer this question).
  19. What do you like most about a girl’s appearance? What do you think is the sexiest thing about a woman?
  20. Have you ever dreamed or fantasized about me?

Tricky financial questions for a guy

  1. Should the money earned by the spouses go into a common “boiler” or should each have their own cash desk?
  2. Should a wife always ask her husband for permission to buy some things?
  3. If a spouse saves a decent amount, for example, on purchases via the Internet, can she consider this money her own?
  4. Should a wife, especially if she does not work, always give her husband an account of the money spent?
  5. In marriage, when buying real estate, who is it better to register it for – for a husband or wife?
  6. Can you trust me with your money?
  7. Would you risk investing in some stocks or assets today?
  8. Should spouses hide the amount of their salary from each other?
  9. Is a wife obligated to save?
  10. What would you like to do if you had a lot of money?
  11. Will you give your wife a salary?
  12. Can you honestly tell your wife what salary you get?

Tricky questions for a guy about work and friends

  1. What kind of person do you consider your boss and how do you treat him?
  2. When you get married, how much time will you devote to your friends, work?
  3. For the sake of your family, will you be able to refuse frequent communication or meetings with friends?
  4. Can you leave your job for the sake of your family?
  5. Would you support your wife’s desire to go to work?
  6. Will you agree if the wife wants to change a well-paid job for her hobby, which does not bring income?
  7. Do you like my friends? (We recommend reading 90 friendship quotes to appreciate it even more)
  8. Can you give up your friends for the girl you love?
  9. Could your wife refuse a romantic dinner for a beer with a friend whom I saw a long time ago?

Relationship trick questions

  1. What does a girl expect from a guy every month?
  2. What is your attitude towards women’s emancipation?
  3. Can you deceive your beloved, knowing that deception is unlikely to be recognized?
  4. I have big breasts, beautiful bust? I am fat? (Learn that a girl should never tell a guy she likes?)
  5. Is it considered treason if your chosen one dances with young people in clubs in your absence?
  6. If you meet an ex-girlfriend who offers you to renew the relationship, what will you do?
  7. Will you continue your relationship with me if I fundamentally do not talk about my past?
  8. Is it okay to open each other’s email without asking?
  9. When will you propose to me and we will get married?
  10. What is your attitude to my style of clothing and how I dress? Do you want me to look different?
  11. Do you want to be alone without me? What causes you such a desire: my behavior, words or something else?
  12. Who should be the first to stop sorting things out with each other in case of disagreement?
  13. What is your attitude to compliments to a woman , how often should they be said?
  14. Is it always necessary to sort things out “to the end”? Whose word should be the last in the dispute?
  15. How would you react to a message from your girlfriend that you need to postpone the wedding? Could this affect your relationship?
  16. What will you do if you are not allowed to date or marry your girlfriend? And if the ban will be up to the deprivation of the paternal inheritance?
  17. Let the girl look through your address book or sms?
  18. Can you tell the girl you like about her shortcomings?
  19. Could you change religion to marry a girl?
  20. Ever bought lingerie for a girl?

Tricky questions for a guy about family/marriage

  1. Who should take the first step towards reconciliation after a family quarrel has arisen?
  2. If your wife does not want to have children, how will you react? Could this be a marriage problem?
  3. How long does a wife need to be on maternity leave?
  4. How do you feel about separation in marriage? Would you let your wife go to a resort alone?
  5. What is your attitude towards living after marriage with your parents or for your mother-in-law to live with you?
  6. Will you be jealous if I closely communicate or be friends with men, for example, work colleagues?
  7. If you have to care for one of the parents, what will you do: hire a person to care for them; you will take care of your parents yourself; Or will you entrust “care” to a nursing home?
  8. Will you agree to adopt adopted children if you don’t have your own?
  9. If some behavior or words of the wife will cause constant dissatisfaction, or irritation, is it worth trying then to save the marriage or not?
  10. How will you react when you find out that someone hit or hurt your child?
  11. Who should go to parent-teacher meetings at school?
  12. Having your own family, can you deny your parents something?
  13. What will you do if the wife cools down to sexual relations?
  14. Would you let your wife change religion?
  15. Who will you love more: the child’s wife or mother?
  16. Would you enter into a prenuptial agreement at the request of the bride?
  17. Can you call your mother-in-law and father-in-law mom and dad?
  18. Will you agree that the bride should leave her last name at the time of marriage?
  19. What annoys you about my parents, family, relatives?
  20. Do I look sexy or not?
  21. What two things do you especially like about me? What’s the only thing about me you can’t stand?
  22. Could you describe me in three words, if so, which ones?
  23. Prefer to be rough, romantic or sensual?
  24. What’s the weirdest thing you fantasized about?
  25. Do you prefer to give or receive?

Tips and Cautions

  1. In the initial courtship period, be careful about asking tricky questions that you have prepared for a guy. Since it is not known what can anger or embarrass him.
  2. Think about the possible consequences: resentment, embarrassment, anger.
  3. It is important to remember: the guy’s reaction to these questions will depend on his nature and temperament.
  4. Don’t try to ask all these questions in a few weeks of courtship.
  5. Don’t fundamentally try to figure out the answer to a question that the guy refuses to discuss.
  6. It is better to ask questions not by testing, but by flirtatious flirting. This will help the guy to be more liberated.


Communication is by far the best way to get to know a person of the opposite sex. One of these possibilities is tricky questions to a guy. It’s kind of a veiled way of getting to know his character.

At the same time, thinking about how to pick up difficult questions for a guy, think about why you want to ask him? Are you asking just for fun, to confuse or is it a flirtatious game?

Some questions on the list may seem uncomfortable, others are tricky or funny. But without them, there will be no complete picture of the way of thinking and character of the guy. These questions can be a fun conversation starter or a fun puzzle to spice up your conversation.