Every couple has a curiosity to know details about their partner. And it is fine if you ask questions that do not trigger any conflicts. But most of the couples jump into asking some tricky questions that may look common but can ensue controversy. Even if you try to make your questions appear less contentious, you are still trying to lead into an argumentative path. Also, couples ask most of these controversial relationship questions when they have met each other over six or seven times. And have developed a good bond to open up.

But still, it is better to be safe than diving into deep water. So, you’ll need to avoid asking these controversial relationship questions when you are in the initial stages of a relationship.

Is there any right time to ask controversial relationship questions?

Ironically, there isn’t any right time to ask any of these controversial relationship questions. However, you can alter the directness and intensity of the questions by making use of subtle words. Toning down your expressions and adding mild sarcasm can mitigate the damage if it were to cause any. But if you feel the instant urge to ask such type of questions on your very first date then be prepared for the backfire that may cause differences in your opinions.

1. What is your opinion about an open marriage?

People like colorful life and hence, they look for entertainment and fun everywhere. That is also one of the reasons why couples wish to have an entertaining married life.

So, either out of curiosity or to suit their fancies, they ask such disputable questions. Although in many countries people have an open marriage discreetly. But in the eyes of the law, it is still considered unacceptable.

2. How many girls or guys have you dated so far?

I don’t know, but I believe almost all couples ask this question to each other at least once in their life. I agree it is out of curiosity, but is there any point? What is the purpose of this question?

Do you want to judge why your partner dumped his Ex? Or do you want to draw inferences, the chances of you getting dumped by your partner? It is one of the controversial relationship questions that may knock down the foundation of your flourishing relationship. So, my suggestion- avoid asking it.

3. How many social media profiles do you own?

Yes, there are men out there who make two or three profiles minimum to either stalk women or troll them. And statistics have confirmed this information. A majority of men prefer having multiple social media profiles for different reasons.

Some have legitimate reasons, while some misuse their fake profiles. But there is no point in asking this question to your partner. That’s because it will give him a sign that you aren’t sure about his genuineness.

4. Do you stalk your ex on social media?

Harsh, isn’t it? But couples do ask this question. Purpose? They want to see if their partner is still interested in their ex or not. First of all, even if you ask this question, nobody is going to give you a genuine reply.

The answer is never going to be satisfactory. So, even if you want to know, then better check your partner’s cell phone. That is the only option. You have got to become a detective, to get the answer. And in this process, you can end up going the separate ways. So? The risk is high, and you may not even get an acceptable answer.

5. What are your views on the extra-marital affair?

Nobody will give you a decent reply upon asking this question. That’s because this question is one of the most controversial relationship questions that couples wish to ask, but they somewhere believe that it will hurt the sentiments of their partner.

The question gives a hint, that if you don’t love your partner enough, then they will seek love outside the relationship. That will put trust and a sense of belonging at stake. Result? Either it will lead to a breakup or divorce.

6. Have you dated two or more women simultaneously?

Of course, it is a reality. In today’s tech-friendly world, it isn’t hard to date one or more women. Several apps and websites give you access to date millions of men and women across the globe. Then why date just one? That is how millennials think.

But if you ask this question, the only safe reply you would receive is a NO, even though your partner has dated multiple women at a time.

Think in this way, if in the future, your relationship grows fonder and stronger, then your partner won’t cheat on you. Keep your expectations minimum and have faith in your relationship. The one who values true love will never cheat on you.

7. What would you prefer, a week without money or a week without coition?

Whoops! Puzzling, isn’t it? If you ask this question on your date, your partner will go through a dilemma. It is a very tricky question. But the motive behind the question is clear. You want to see which material blessing holds more importance to your partner.

But it is wrong; everyone seeks material pleasure. And money is the cruel reality of life. You cannot feed yourself if you don’t have money. And the other is a physical need.

So, you must avoid asking this controversial relationship question. If you learn how to strike a balance between what is necessary and what is unnecessary, you will lead a happy life.

8. Do you think fling is bad?

What do you think? Is fling bad? I think it is not if you are clear with your partner that you are not seeking any commitment, and it is only a casual relationship. But asking this question on a date can put your partner in shock.

Your partner may start having second thoughts about you. Also, you may lose a potentially good partner if he gets cold feet.

9. What if I tell you that I had a crush on your best friend before dating you?

Whether you had a crush or not, it is better you keep this little secret to yourself. Why open up and ruin the moment? That will also destroy their friendship. It will give rise to jealousy.

Never say anything that will jeopardize your bonding with your partner. This is one such controversial relationship question that will wreak havoc in your relationship for sure.

10. Did you cheat on any of your exes?

Ok, if you want to be sure of whether your partner won’t cheat on you, then seek commitment from him. Do not ask a question that will give him a hint that you do not trust him completely.

It is not that brutal question, but you are indirectly questioning his integrity and loyalty. Even if he has cheated on his Ex, do you think he will give you an honest answer?

11. Do you like experimenting in relationships?

All right, the definition of experimenting may be different for every couple. But to be specific, I am talking about the boisterous group fun. If you ask your partner whether they like trying new things in relationships to have fun, then you may be showing the dark side of yourself.

While some men will take it lightly some may question your commitment. You must avoid such controversial relationship questions in the initial dating period.

12. If I tell you that I want to visit Amsterdam alone, will you have any problem?

We all know what Amsterdam is famous for. So, if you ask your partner, does he sees any problem in you visiting Amsterdam alone, may cause a bit of confusion. Why would anybody like to visit such a fun place alone?

The obvious answer will be to enjoy an exciting week. But why without your partner? So, do you see the problem here? Your partner may lose confidence in you. He will start believing that you may look for some time alone to have some high-spirited fun without him.

13. What if I go on a vacation with a group of boys, will you be ok? One of the most ridiculous controversial relationship questions

This question gives a hint that you want to test your partner’s patience. No man who is caring and a bit possessive will be happy to see his girl with a group of other guys. Even if they are her best friends.

It is natural to feel jealous and protective of your girlfriend. So, my suggestion is, do not ask such type of questions that may enrage your man.

14. What if I ask you that I need a month’s break (for no reason), is that ok with you?

If you have had no fights, and everything is going smooth, then why would you ask for a break? This question gives rise to suspicion. Such controversial relationship questions destroy the essence of a beautiful relationship.

If you want to maintain some distance, then tell your partner without hesitation. Why create doubts and leave your man brooding about what wrong he did? Instead, give him a valid reason and take a break.

15. Did you have any secret love encounters in life? These types of controversial relationship questions may irk your partner

To give you an example, let’s say that you run into your school crush at a mall after a long time, and you discover that your schoolmate also has a crush on you. So, you fulfill your fantasies with her (with consent) and promise never to see each other again.

And if you ask your partner this type of controversial question, then you are not going to get a breathtaking reply. That’s because nobody likes revealing their deep-dark secrets. At least not to their future partner.

16. Have you ever lived with a stranger for fun?

Anyone who answers this question is eccentric. But in a good way. People like exploring themselves. Everybody wears a mask, and nobody likes revealing their true self. But when you are with a stranger, and you feel that person cannot harm you, then you may disclose in and out about yourself; and enjoy their company.

But if you ask this question to your partner, then you will never receive any impressive response. People will always give you diplomatic replies. That’s because they are scared of being judged.

17. Do you like the idea of swapping your partner? One of the riskiest controversial relationship questions ever

It may sound fun, but it is not. When you ask such questions, you are feeding your man’s brain with unwanted ideas. Such erratic ideas are not helpful. If you wish to open up to share your fantasies, then state them in clear words.

Do not beat about the bush. Also, accept the fact that if your partner is way too serious about the relationship, then this question may hurt his sentiments. You may lose a loving and caring partner.

18. What if I become disabled, will you keep loving me?

It will be unfortunate if you ever meet with an accident and your relationship suffers a setback. But whether your partner will keep loving you or not depends on three factors- bank balance, true feelings, and empathy.

If your partner truly loves you, he will take care of you. But nobody in life will ever give you a commitment in such situations. Thinking of such unfortunate situations itself gives heebie-jeebies.

19. A big no to ask these types of controversial relationship questions- Will you ever choose money over me?

If you become hard on your man, he will undoubtedly choose money over you. So, before you ask this question, ask yourself how do you treat your partner. Furthermore, let’s not forget that money plays a pivotal role in everyone’s life.

So, if your partner doesn’t love you back, then he will choose money over you regardless of how you treat your partner. So, never try to compare yourself with money. Money is important no matter what. That is the reason such controversial relationship questions destroy everything before anything good commences.

20. Is it ok if I leave you alone to enjoy my ‘me time’ for a week? It may sound a bit weird to ask such controversial relationship questions

Partners think that you can enjoy your me-time any time of the day. Then why do you need a week’s break to enjoy without them? This question gives a sign that you want to decide how you can break up with them.

To look for solutions, you need some time alone; hence you want to take a break. So, it is a very tricky question. And maybe your partner may keep an eye on you to see what would be your next move.

21. What if you come to know that your friend has a crush on me?

Mostly these questions are asked by women. They like inducing envy in their men. But the problem is when you try to infuse negativity in someone’s head, you are trying to dig a hole for yourself.

What is the purpose of this question? Would you like your man to fight with his friend for you? Always remember, if your man loves his friends more than you, then you will lose him forever.

22. If we get married, and things get onerous, will you divorce me? Try to avoid such controversial relationship questions

Firstly, if you get hard on your partner, then he will divorce you for sure. Both partners need to be of sound mind when making a decision about their life. Marriage is a journey; things are bound to get difficult.

So, if you aren’t sure your partner will be supportive, then do not get married. Asking this question will not solve your doubts.

23. Do you have any backups (in terms of another woman or man) in life?

You should ask this question to yourself first. Do you have a backup? If yes, then everyone has a backup. Most couples have a backup plan ready before they get hitched. Backups do not necessarily mean you have an affair.

It simply means, that if things don’t work out with your current partner, you know where to go and whom to approach (to seek solace). It could be your friend, neighbor, or schoolmate.

24. Will you forgive me if I cheat on you? This is one of the highly preposterous controversial relationship questions

It is not a wrong question, but it is a controversial relationship question. But before you ask your partner, you must contemplate. Will you forgive your partner if they cheat on you?

25. Will you give me another chance to start afresh if you come to know I got laid after getting drunk?

No one likes a cheating partner. If you got laid because you were inebriated, that doesn’t mean you aren’t a cheater. You are a cozener and if you cry foul, it means you know how to deceive others.

Let’s get your intention straight. Do you think you can cheat on your partner? If yes, then you must also have the courage to forgive your partner if he cheats on you.


These questions are controversial if you ask them on the first date itself. Once you get along and have dated for a couple of weeks, you develop a good understanding, your wavelengths may match, and maybe post this comfort level establishment you can ask these controversial relationship questions.

There is nothing wrong with seeking clarity in the relationship. The questions may look controversial if you happen to ask them bluntly. However, if you twist them or use an indirect approach to ask these questions they won’t sound controversial.

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