Tricky questions for a guy: 100 provocative questions for a man

Why are tricky questions interesting to a guy?

Questions like these can add some fun to a conversation with a guy, making it more interesting than usual. This is a kind of master class in polishing knowledge about men. So we definitely recommend that girls have a list of these questions for their boyfriend in their communication arsenal.
The answers to these questions help to understand the difference between male nature 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 sneaky 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 that you can ask a guy to get to know him better will also help with this).
Tricky questions are tricky questions that are difficult to answer unambiguously. This means that the guy will have to use his brains to answer them. This will help the girl see his real, unfeigned character.
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 a play on words, 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 incorrect.

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

A few words to think about:

When you use these questions to get to know a guy, you are trying to establish a connection with him.

Conversations are not meant to impress people. Instead, they create a bridge where the two of you can meet halfway and move beyond formal communication.

Remember that the deeper the connection, the stronger your relationship with that person.

Now it's time to ask yourself how well you really know the person and evaluate your relationship with them. We hope you enjoyed these questions to get to know a guy better.

Trick questions for a guy

Can you lie without saying a word?
If not now, then when?
Do you persist in what you should give in to?
Is male crying a sign of weakness or strength?
Would you break the law to save someone you love?
Do you like what you have?
When all is said and done, will you continue talking or will you start doing?
If your brother talked to you the way you talk to others, how long would your friendship with him last? (We recommend reading meaningful quotes and statuses about brothers to appreciate them even more)
Time or money?
Is it better to listen to the brain or the heart?
Should there be a hierarchy in a family?
Do you find older women attractive?
Could you marry an ugly woman, but a rich one?
What do you look for in a girl?
Is it better for a girl to use a cool or sassy 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

Are you deceiving others? How often, in what case?
In a relationship, who should have primacy: a man or a woman?
What would you do if you had the opportunity to be invisible or a woman for a whole day?
What is one thing you will try to save if the house suddenly ends up on fire?
Which of your friends' girlfriends do you compare yourself to most often? (We recommend reading 20 Tricky and Provocative Questions to Ask in a Group of Friends).
Given the opportunity to commit any crime with impunity, what will you do?
What is better for a man: to be smart and ugly or dumb but beautiful?
Given the ability to lock anyone in a mental hospital, who would you lock?
What is most important for a girl to have: attractiveness, intelligence or beauty? Which one do you prefer?
There are different opinions on how often men and women should take a bath. What do you think?
How often should a man and woman change their underwear or socks?
Can you tolerate bad breath, sweat or dirty clothes? Should we talk about this if this happens?
Does it irritate you when a person burps or passes gas?
Have you ever had mental disorders?
Does this suit me...?
Will you buy me...?
Does a man like receiving gifts?
Who is more important to you: mom or girlfriend? (We recommend reading 104 quotes about mom that will help answer this question).
What do you like most about a girl's appearance? What do you consider the sexiest thing in a woman?
Have you ever dreamed or fantasized about me?

When meeting

Regardless of age or gender, when meeting people, they behave reservedly and shyly. When under nervous tension, women talk too much, and men prefer to remain silent. The guys need to talk. It's better to do this with simple questions. For messages, choose topics of sports, travel, hobbies, and views on life in general.

For dating, making friendships, close relationships by correspondence, the following questions are suitable:

Do you have free time to chat with a beautiful (interesting, original) girl?
Have you looked at my profile, did you like my photos?
Can you help a good person you don’t know selflessly?
Can you tell us about your work (hobbies, friends, family)?
Who's your sign?
You recently had a BD, as noted?
Do you like surprises?
What sports do you do?
Do you want to take an interesting test about who you were in a past life?
How long have you been to the cinema (theater, concert, football)?

The beginning of a relationship does not oblige the girl to anything; ask the guy questions on any topic. At the moment of recognizing the interlocutor, not only the answer is important, but also the manner of communication, tone, and speed of SMS arrival. Also pay attention to whether the man asks you questions. If not, then there is no point in counting on a serious relationship, the interlocutor is not interested in you or is married.

On a note! If a man has become even more constrained and tense after a series of messages, try complimenting him in a humorous way. But don't make fun of his silence.

Tricky questions for a guy about finances

Should the money earned by spouses go into a common “pot” or should everyone have their own cash register?
Should a wife always ask her husband's permission to buy certain things?
If a spouse saves a decent amount, for example, on online purchases, can she consider this money her own?
Should a wife, especially if she does not work, always give her husband an account of the money spent?
In a marriage, when buying real estate, who is better to register it in the name of the husband or wife?
Can you trust me with your money?
Would you risk investing money in some stocks or assets today?
Should spouses hide the amount of their salaries from each other?
Is the wife obliged to save?
What would you like to do if you had a lot of money?
Will you give your wife her salary?
Can you honestly tell your wife what salary you receive?

In addition to tricky questions, girls and guys are also interested in more frank topics. We advise you to read: What intimate questions do girls and guys want to know each other’s opinion?

Can any topics be discussed?

At the very beginning of the conversation, we said that the guy could be asked questions on any topic from the list of decent ones. And what is indecent, you will understand for yourself when you think about what question you would absolutely not want to answer. Each person has his own sore subject, try not to bring up those layers that he does not want to stir up. If you are constantly met with his excessive secrecy, perhaps he never became yours.

Try to avoid topics that are unpleasant to him

Tricky questions for a guy about work and friends

What kind of person do you consider your boss to be and how do you feel about him?
When you get married, how much time will you devote to your friends and work?
For the sake of your family, can you give up frequent communication or meetings with friends?
Can you leave your job for the sake of your family?
Would you support your wife’s desire to leave to earn money?
Would you agree if a wife wants to exchange a well-paid job for her hobby, which does not generate income?
Do you like my friends? (We recommend reading 90 quotes about friendship to appreciate it even more)
Can you give up your friends for the girl you love?
Would you be able to refuse your wife a romantic dinner for the sake of beer with a friend you saw a long time ago?

Trick questions about relationships

What does a girl expect from a guy every month?
What is your attitude towards women's emancipation?
Can you deceive your beloved, knowing that the deception is unlikely to be recognized?
Do I have large breasts, a beautiful bust? I am fat? (Learn what a girl should never say to a guy she likes?)
Is it considered treason if your chosen one dances with young men in clubs in your absence?
If you meet an ex-girlfriend who asks you to reconnect, what will you do?
Will you continue your relationship with me if I don’t talk about my past on principle?
Is it acceptable to open each other's email without asking?
When will you propose to me and we will get married? (Read: How to propose marriage to a girl?)
What do you think about my clothing style and the way I dress? Do you want me to look different?
Do you want to be alone without me? What makes you want this: my behavior, words or something else?
In case of disagreement, who should be the first to stop sorting things out with each other?
What is your attitude towards complimenting a woman, how often should you say them?
Is it always necessary to sort things out “to the end”? Whose word should be the last in the dispute?
How do you react to a message from your girlfriend that you need to postpone your wedding? Could this affect your relationship?
What will you do if you are banned from dating or marrying your girlfriend? What if the ban goes as far as deprivation of the father’s inheritance?
Will you let a girl look through your address book or SMS?
Can you tell the girl you like about her shortcomings?
Could you change your religion to marry a girl?
Ever bought lingerie for a girl?

Tricky questions for a guy about family/marriage

Who should take the first step towards reconciliation after a family quarrel?
If your wife doesn't want to have children, how will you react? Could this be a problem for a marriage?
How long does a wife need to be on maternity leave?
How do you feel about separation in marriage? Would you let your wife go to the resort alone?
What is your attitude towards living with your parents after marriage or having your mother-in-law live with you?
Will you be jealous if I communicate closely or be friends with men, for example, work colleagues?
If you have to care for one of your parents, what will you do: hire someone to care for them; you will look after your parents yourself; or will you entrust the “care” to a nursing home?
Would you agree to adopt foster children if you don’t have any of your own?
If some behavior or words of the wife cause constant dissatisfaction or irritation, is it worth trying to save the marriage or not?
How will you react when you find out that someone hit or hurt your child?
Who should go to parent-teacher conferences at school?
Having your own family, can you refuse your parents anything?
What will you do if your wife cools down to sexual relations?
Would you allow your wife to change religion?
Who will you love more: your child’s wife or your mother?
Would you enter into a prenuptial agreement at the request of the bride?
Can you call your mother-in-law and father-in-law mom and dad?
Do you agree that the bride should leave her last name when getting married?
What irritates you about my parents, family, relatives?
Do I look seductive or not?
What two things do you especially like about me? What's the one thing about me you can't stand?
Could you describe me in three words, if so what?
Do you prefer to be rough, romantic or sensual?
What's the most unusual thing you've fantasized about?
Do you prefer to give or receive?

Tips and Cautions

During the initial period of courtship, be careful when asking the tricky questions that you have prepared for the guy. Since it is unknown what could anger or confuse him.
Think about the possible consequences: hurt, embarrassment, anger.
It is important to remember: a guy’s reaction to these questions will depend on his nature and temperament.
Don't try to ask all these questions in a few weeks of courtship.
Don't try to fundamentally figure out the answer to a question that the guy refuses to discuss.
It is better to ask questions not in a testing way, but in a flirtatious way. This will help the guy be more relaxed.

For additional reading, we advise you to find out how a girl can interest a guy and keep him near her?

Conclusion

Communication is by far the best way to get to know someone of the opposite sex. One of these opportunities is asking tricky questions to a guy. This is a kind of veiled way to find out his character.

At the same time, when thinking about how to choose difficult questions for a guy, think about why you want to ask him? Are you asking just for fun, to embarrass, or is this a flirty game?

Obviously, some of the questions on the list may seem awkward, others are tricky or funny. But without them there will be no complete idea of the guy’s way of thinking and character. These questions can be a fun conversation starter or an interesting puzzle to add spice to your conversation.

Watch the video to see how difficult it is for guys to answer tricky and difficult questions.

Girls, draw your own conclusions

The trickiest questions can only be asked to strong, self-confident and adequate men. Unfortunately, not all guys are relaxed, so before asking something like that, you need to gain trust and loosen up your interlocutor. Particular attention should be paid to the environment so that it is conducive to a frank conversation.

If a young man is tired and cannot boast of a good mood, tricky questions can only lead to rudeness. Also, you should not put pressure on him with your erudition and sharp mind if this belittles his mental abilities. You can talk about general things and concepts with a guy you don’t know well; personal and intimate questions are asked only in an established relationship.

Author's rating

Author of the article

Elena Milkova

28 years old, psychologist, sexologist. I consider myself an expert in dating and relationship development.

Articles written

Tags: Helping girls, Dirty

List of dirty questions for a guy
What questions can you ask guys and what questions shouldn’t you?
What to write to a girl when meeting VKontakte: examples