TOUGH RELATIONSHIP QUESTIONS: 91+ Questions to Ask in 2023

Sometimes you have to ask the tough relationship questions (even if you don’t want to hear the answers) to address the issues and emerge stronger. Tough relationship questions can thus foster trust, openness, and communication, resulting in a happier, healthier relationship.

The problem is that couples frequently avoid discussing tough relationship questions. They become comfortable or fear the “consequences” or any change that may result. But keep in mind that change is a good thing.

Are you two just drifting along? Have you grown too accustomed to your surroundings? Are there underlying issues that, if they aren’t already causing issues, could break you down the road? Have certain things gone unspoken? What are the most important things?

Asking tough relationship questions isn’t about inventing problems that don’t exist. It’s about “checking in,” knowing where you truly are and ensuring that any issues or challenges are dealt with before they arise.

It doesn’t have to be tough to ask difficult relationship questions. If you improve your relationship’s openness and communication, it no longer appears that way. So, my friends, give it a shot…

When Should You Ask Tough Relationship Questions?

Choose your moment to ask tough relationship questions. Bring it up when both of you are calm, willing, and in a relaxed, loving space. Because you will not get the answers, you seek! It also won’t work if you bombard your partner with these “bad boys” as soon as they get home from a tough day at work!

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Instead, wait until you’re both ready. Remember, the purpose of these tough relationship questions is to help and strengthen your relationship and communication. So there’s nothing to be afraid of! They are here to assist you.

Most issues can be resolved if adequately addressed – and that’s precisely what you’re doing with these challenging relationship questions!

Tough Relationship Questions

So, now that we’ve covered all of that let’s get started on these tough relationship questions. Use these questions as inspiration and ideas for challenging relationship questions you may need to ask or would benefit from asking.

Scroll through, take it all in, jot down any questions you have, and use it to expand on your ideas.

91 Tough Relationship Questions

So, in no particular order, here are our tough relationship questions:

• Are you content in your relationship?
• What can I do to make you happy? What qualities do you think makes me a good partner?
• Are you satisfied with where we are now? Do you believe the relationship has progressed too quickly, too slowly, or just about right? How at ease do you feel with everything?
• What am I doing that makes you unhappy? What could I do better?
• Do you believe you and I are truly compatible? In what ways, if at all?
• What do you think we’re doing now, and do you think we’re on the same page about how / where we’re going?
• In what ways do you believe we bring out the best and worst in one another?
• Do you think we’re connecting well in all of our various ways? Are you content with the physical and emotional intimacy we share?
• How do you think our relationship has changed (for the better or for, the worse) since we first met?
• How do you think we’ve changed (for the better or, the worse) as individuals since we first met?
• Do you believe your emotions are as strong now, if not stronger, than they have always been? Why and why not?
• How well do you believe we handle conflict and communicate about complex issues?
• And how well do we both deal with our emotions as individuals?

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• What do you believe causes the most problems and conflicts in our relationship? Is this something that can be resolved properly and permanently? If so, how do you think we should go about it? What are some things we should or could try?
• Is there anything you think we promised to work on but didn’t?
• What have we accomplished that you are proud of us for? And what do you think that demonstrates?
• Is there anything you’re still holding on to from a previous conflict? Or is there anything you can’t seem to let go of or get over? Let’s talk about the things that are bothering you so we can get rid of them!
• How easy is it for you to forgive the mistakes I/we may make in our relationships? And are there any things you consider unforgivable? What are your limits? What were you unable to overcome, or do you believe a couple should not be able to overcome? (Because it’s simply excessive!)
• What do you consider to be a healthy and unhealthy relationship?
• How have your previous relationships influenced the way you are in your current relationship?
• Is there anything you think I should change but don’t think I will or can? And do you think these will stymie our relationship in the future?
• What is the most crucial relationship lesson you’ve learned since you’ve been with me?
• Is there anything about being in a relationship that scares you? Do you have any general relationship apprehensions, concerns, or fears? What is your perspective on love and relationships, and what does it mean to you?

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• Where do you see us going in the next two, five, or ten years? Alternatively, where would you like to see us? And how likely do you believe this will occur?
• How serious are you about this relationship? What are you willing to do, or not willing to do, to make it work?
• Is the relationship satisfying to me physically, emotionally, rationally, spiritually, and financially? Do I want to keep going?
• What would be the worst-case scenario if things didn’t work out between us? Is it worth putting everything on the line for this person?
• Can we resolve conflict maturely and calmly? Or do we simply lash out at each other?
• Do we plan to buy a house together or rent? Are we putting money aside for retirement together or separately?
• What does it mean to be obsessed with your partner even when you’re not together?
• How long do I want to be in this relationship?
• What do I anticipate from my partner?
• What happens when one person wishes to have children, but the other does not?
• How do we make financial plans for the future?
• What if one person wants to leave home, but the other does not want to leave their family behind?
• Do you have any plans for how long you’ll be together before making major decisions such as marriage, children, career, health, and wealth?
• What do you believe will happen if something goes wrong in your relationship, such as one of us becoming ill or losing our job?
• What if one of us cheats or becomes abusive to the other?

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• Do we have a plan for dealing with financial insecurity, or do we just hope everything works out?
• What does it mean that we fight so much?
• What about when we disagree on issues such as religion or politics?
• Do I believe they will change?
• Is it true that we have chemistry? Or is it just a crush?
• Do we share enough interests? Do we share the same goals in life?
• Do you believe we have the same desires at the same time? And how important is timing to you?
• What are our plans for raising our children? What are the values we want them to have?
• Do you have any reservations, fears, or reservations about us and our relationship? And how long have you been feeling this way? Also, where do you think they’re coming from, and how credible do you think they are?
• What would you change about our relationship if you could?
• What do you find most appealing about me? There are big things and little things. (As you can see, difficult relationship questions can also be positive.) It can also refer to something you don’t tell the other person enough of).
• Are there any topics you’d like to discuss? But which do you find difficult to raise?
• Or anything else you’d like to talk to me about but find it challenging to do so? (For example, because of relationship anxiety, excessive worry, or toxic behavior.)
• What do you consider to be some of our best and worst moments?

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• Do you believe we fully comprehend each other? Let’s go deeper into this — how do you understand me, and what do you think I don’t fully “get” about you and your personality?
• Do you think we’ll be able to read each other well? For example, if one person is depressed, the other can tell without having to say anything. And if not, what’s the point? Is it because they aren’t paying attention or because the other person is still closed off? Let’s go over everything.
• What makes you feel close and connected to me? What makes you feel close and connected to me?
• Do you believe I pay enough attention to the things that matter to you? Alternatively, ask enough questions about yourself and your life.
• Do you believe the relationship is ever one-sided, that we’re both putting in the same effort and feeling the same way? Do you ever feel as if your or my needs are not being met? Or that one of us doesn’t feel as strongly as the other?
• What is your preferred method of giving and receiving love? What is your primary love language? (You both must understand this one.)
• How about attachment styles? Do you believe we have similar or dissimilar attachment styles, and do you think this has any bearing on our relationship or how we interact with each other?
• How do you feel about our relationship with each other’s friends and family? How well do you believe we complement each other’s lives? Is this working, or could it be made better?

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• Do you believe we spend enough time together? Or, on the other hand, spending too much time together? Is the relationship clingy or suffocating?
• Do you think you can still do everything you want, apart from me? Have we struck the proper balance?
• Have you lost sight of yourself since being with me? Or have you noticed a shift in how / who I am?
• How far have you/we had to go in this relationship? Is that a standard/healthy/acceptable amount? Let’s talk about it.
• Do you believe we trust each other, and how strongly do you think our trust is? How well was our trust rebuilt if it was ever broken? And what can we do to keep building on and strengthening our trust so that we both feel delighted and secure?
• Do you ever get the impression that we take each other for granted? If so, when and how? (You could also do an appreciation exercise with this to recognize how fortunate you both are right then and there.)
• Do you ever experience jealousy? In what kinds of circumstances? And how do you handle it? Is there anything else I can do to assist you? (After all, you’re a group!)
• Do you believe we’ve witnessed each other at our best and worst? And what era were we living in?
• Would you change anything about our relationship if you could go back in time and change anything? If so, what is it, and why is it so? And what do you want us to take away from it?
• Do you have any further questions for me? (The challenging relationship questions you choose to ask your partner should elicit more / any responses from them as well.)

Questions You Should Ask Your Partner

Now that we’ve gone over the top tough relationship questions based on what happens most frequently in relationships. However, this is only a guideline – a list of the kinds of questions you MIGHT want to ask.

Consider your relationship and make sure the questions you choose are specific to the two of you when deciding what tough relationship questions to ask.

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• Have any incidents been swept under the rug and not properly addressed?
• Is there anything that seems to come up again and again?
• Have you ever had a conversation about a topic that didn’t seem to get resolved? (Perhaps the right questions were not asked in this case, and the full willingness to listen and act was not present.)
• Is there anything you’d like to discuss or learn more about but are too afraid to ask?
• How is your communication style? Do you frequently discuss the “big stuff” or not? And how much closer could you get to it if you could talk about these things?
• How do you think you and your partner could improve your relationship? In which region? So, what kinds of discussions could you have to encourage and support this?

Conclusion

So we have tough relationship questions, as well as how to establish the kind of questions you may need to ask in your relationship to strengthen it further. Simply be brave. Have faith in yourself. And be completely open in your communication. You can get through almost anything if you are open, willing, and willing to put in the effort!

Frequently Asked Questions