If You Really Want To Know Your Lover, Ask These 25 Controversial Relationship Questions

You’ll want to stick to safe conversation subjects during the first few dates with a new person. However, as a relationship grows, the urge will strike to dig deeper into what makes someone tick. 

After all, how will you ever really know your lover unless you delve into controversial relationship topics? 

You can ease into delicate conversations by suggesting that you debate some hypothetical relationship scenarios for fun and see where it takes you.

What Are the Most Important Questions to Ask in a Relationship?

For your relationship to succeed, you need to be compatible with your partner.

You don’t have to share every opinion or point of view, but you should agree on the bulk of issues that define your lives. Otherwise, you’re setting yourself up for conflict instead of joy and intimacy.

Ask questions like these to find out where your lover stands:

  • Do you see yourself wanting children?
  • What would you consider cheating in a relationship?
  • Is religion important to you?
  • What are your political views?
  • What are your lifestyle preferences?
  • How would you describe your attitude toward money?

25 Controversial Relationship Questions to Really Know Each Other

Questions are only controversial if you and your lover have opposing views. 

Of course, you won’t know if you’re in opposition unless you ask, but you might have to brace yourself for some unexpected answers.

1. Do you think you can fall in love with more than one person at once?

People’s views on romantic love fall into one of two camps. The first experiences love as an exclusive feeling, while the second is open to the possibility of encountering another person worthy of love.

2. Do you love me enough to die for me?

You probably imagine some heroic scenario where your lover gives you the only spot on a lifeboat. In reality, this question can only honestly be answered in the heat of the moment when heroism is possible. 

Otherwise, your partner might feel obligated to commit to the ultimate sacrifice for the sake of pleasing you.

3. If we weren’t together anymore, would you envy who I was dating?

Realistically, the circumstances that end your relationship would dictate future feelings about this. After a bad breakup, your current partner might be glad to be rid of you and just pity your new paramour. 

Outside of that nasty scenario, someone who really loves you would dislike the thought of you with anyone else.

4. What kind of parent do you think you’d be?

You can explore this topic to get a feel for your partner’s perspective on parenthood. Many people fear the responsibilities of parenthood, even people who want kids. This question opens the door to people who don’t want kids, informing you about what raising children alongside this person would be like.

controversial relationship questions

5. What would you think of me if you learned I cheated in a previous relationship?

Generally, people have a low opinion of people who cheat on their partners. No one is going to answer that it’s OK to cheat. Many people choose not to discuss their past relationships due to the uncomfortable feelings the topic might trigger. This question can threaten trust.

6. Would you break up with me if you started making more money?

An income disparity can create insecurity in a relationship. You might think someone dates you because of the monetary advantages. 

Fear of being reduced to a paycheck could prompt you to ask this question, but is it possible to answer honestly? At worst, the question invites a money fight. At best, you might hear a lie.

7. What do you think about when we make love?

Answering this question could be difficult. Do you keep a journal of what crosses your mind when you’re getting busy? Do people even think about much in the throes of passion? 

A question like this puts a person in a difficult situation. Concern about saying the wrong thing and hurting your feelings would tend to produce safe responses like “I think about you!”

8. Am I the top priority in your life?

Presumably, you are a big priority as a romantic partner or spouse. The trouble here comes from the fact that people can have competing priorities. 

People tend to view their children as their top priorities. Other close family members can qualify as equally important. Your partner’s actions should show you how big of a priority you are.

9. What do you find attractive about me?

Knowing what someone sees in you is good information to know. This conversation can go beyond physical features. 

Personality traits and principles attract people as well. This question could launch a conversation that helps both of you deepen your understanding of your romantic chemistry.

10. Do you think that you can do better than me?

When you say this, your insecurity is showing. Maybe your partner will pick up on the fact that you need some reassurance and shower you with gratitude and praise. 

Any answer will help you gauge how much value your partner places on the relationship. The controversial aspect of this question comes from the strong possibility your partner won’t be honest.

11. What things about my personality bother you the most?

We all can be blind to our shortcomings. An honest discussion about areas where either of you can improve could help your relationship flourish. 

On the other hand, handling criticism is difficult, and criticism from someone you care about can be the hardest of all. Unless both of you are ready to be good sports, this might be one of those fun debate topics for couples to stay away from.

12. Am I giving you what you need from a lover?

Feedback can help a couple develop an intimate relationship. Talking about fulfilling each other’s physical desires could increase your level of intimacy. 

When you ask this question, you might expect your partner to reciprocate and ask if you need anything more. If this doesn’t happen, then you might have evidence that your lover doesn’t spend much time thinking about your needs.

13. If I wanted an open relationship, would you break up with me?

Be sure to broach this topic once you’ve established that you want to talk about controversial subjects. Asking it out of nowhere would leave most people with the impression that you want an open relationship.

 Whether your partner says yes or no will inform you about the relationship’s direction.


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14. Could you get over it if you found out I kissed someone else?

Even when people accept that others have the right to do what they want, jealousy can be extreme. Most people want to be in relationships that make them feel special. 

Being affectionate with someone else strips them of that feeling. Most people would not know how to answer because the truth only comes out once you cross that bridge.

15. Do you think it’s OK to exchange sexy texts with other people?

Many people enjoy being flirty with their phones because it’s not the same thing as physical touching. Others would see this behavior as crossing a line because it could develop into physical affection. 

A minority of people might be comfortable with it if they are not looking for a long-term, committed relationship.

16. If I didn’t satisfy you in bed, would you leave me?

Talking about this topic tells you how strong sexual relations are to your partner. You could discover that your partner sees this as just one aspect of a relationship built upon other essential elements of compatibility.

17. Could your friends convince you to dump me?

People value their friends’ opinions, and their influence can be strong when they dislike who you’re dating. Whatever the outcome of the conversation, you’ll gain insight into how your lover makes decisions. Some people follow their hearts, but others place more weight on what others think.

18. How many people have you had sex with?

controversial relationship questions

Watch out if you choose to enter this territory. Having many partners or very few partners could alter your perception of the person. 

Most people choose to keep this information private because they want to focus on their current relationships and leave the past in the past.

19. Do you think it’s normal for people to take breaks from their relationships?

On-again-off-again romances are not unheard of. Talking about this could help you know if you could rebuild a relationship should you break up for some reason. 

The answer might also be important to you if you’re thinking about moving away for school, military, or a job.

20. Do you think of me when you masturbate?

A question of this nature delves deep into the other person’s privacy. Sexual fantasies are often just that: fantasies without expecting them to become a reality. 

Self-pleasuring is, by definition, very personal. If you’re lucky, your partner will answer, “Yes, I think of you!” But who knows if it’s true?

21. Do you believe it’s OK to dump someone for gaining weight?

Relationship counselors have had to tackle this subject over and over. For most people, some weight gain is inevitable as the years go by. 

The truth is that some people find excessive weight gain a turn-off. It could be a deal-breaker, and you might want to know your partner’s view on the matter.

22. Are you still in love with your ex?

Not all breakups are a mutual decision. Your new love interest might still possess a longing for a previous partner. 

Whether that person confesses that to you is another question. If they do admit to still loving their ex, you may need to step back from the relationship until your new person deals with these feelings.

23. Would you break up with me if you disliked my parents?

They say if you want to know what somebody will be like in the future, look at their parents. 

Things might be rosy until an encounter with parents sends the relationship to the fight club. Entering a long-term relationship with someone whose parents are toxic can be difficult.

24. Would you break up with me if I got a great job in another city?

Moving with your partner due to a new job is a huge step. You give up your home and perhaps have to start over with your career. Some relationships survive this, and some don’t. 

Among relationship scenario questions, this one is very plausible. You just might want to discuss this hypothetically to measure each other’s level of commitment.

25. Would you care for me if I got super sick or badly disabled?

People who’ve never had to be a caregiver might be quick to say that, of course, they would stand by a partner. 

Unfortunately, lovers or spouses sometimes abandon their sick partners because the strain is too great. For this reason, “in sickness and in health” is in marriage vows, and it’s a primary responsibility of marriage.

Dating and relationships function as a prolonged job interview. You’re always looking for confirmation that you should be together or trying to unearth a deal-breaker. 

Don’t ask controversial relationship questions to start a fight. See them as an opportunity to learn more about your lover and discover how compatible you actually are.            

There are plenty of things we are curious about when entering a relationship. Here are some of the controversial relationship questions you can ask to your partner.