50 Tough Relationship Questions

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Sometimes, you have to ask the tough questions (even if you don’t necessarily want to hear the answers), to address the things you need to, and come out of it stronger. Tough relationship questions can therefore build trust, encourage openness, improve communication and overall, create a happier, healthier relationship. 

The thing is, couples can often shy away from tough relationship questions. They get comfortable, or fear the “consequences” or any change that could come of it. But remember – change is a good thing.

Are the two of you just drifting along? Have you become too comfortable? Are there underlying issues there that – if are not already causing problems – could only break you later down the line? Have certain things been left unsaid? Things which are important?

See, asking tough relationship questions is not about creating problems that aren’t there. It’s about “checking in”, knowing where you’re truly at and ensuring that you squash any issues or challenges before they come.

Asking tough relationship questions doesn’t have to be a big deal. In fact, if you improve the openness and communication in your relationship, it doesn’t seem that way at all. So give it a go my friends, give it a go…

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Important Questions To Ask Your Partner

Now we’re about to run through the top 50 tough relationship questions, based on what’s most common in relationships.

However, this is just a guideline – a list of the kind of things you MIGHT want to ask more than anything. 

When considering what tough relationship questions you NEED to ask, look at your relationship and make sure the questions you choose are specific to the two of you…

  • Are there any things that have happened, that have been brushed under the carpet and not properly addressed?
  • Are there any “issues” that seem to crop up, time and time again?
  • Have you had conversations about a topic before, but it hasn’t seemed to have got resolved? (In this case, perhaps the right questions haven’t been asked and the full willingness to listen and take action, just wasn’t quite there.)
  • Is there anything you kind of want to talk about, or find out about, but you’re too afraid to ask?
  • What is your communication like? Do you often talk about the “big stuff” or not? And how much closer could it bring you, if you were able to talk about these kind of things? 
  • How do you think the two of you could strengthen your relationship? In which area? And so what kind of conversations could you have, to better encourage and support this?

These are just a few things you may like to consider, to start to get you thinking.

Like I said, the very best tough questions to ask your partner, will be the most specific and relevant to the two of you, and your relationship.

So choose “wisely!” Have the conversations that the two of you need the most. Because that, my friends, is what’s going to make the biggest (POSITIVE!) difference. Okay?

Tough Relationship Questions

When’s The Best Time To Ask Tough Relationship Questions? 

When it comes to asking tough relationship questions, pick your timing. Bring the conversations up when you’re both calm, willing and in a relaxed, loving space. 

(Don’t ask in the middle of an argument, anyway – that’s one thing for sure. As you just won’t get the answers you want to hear! Nor will it work well if you bombard your partner with these “bad boys” as soon as they’ve got back from a tough day at work!)

Instead, do it when you’re both ready. Remember – these questions are to help and strength your relationship and communication. So they’re nothing to fear! They’re here to help you.

Most issues can actually be worked through, providing they’re properly addressed – and that’s exactly what you guys are doing with these tough relationship questions!

Just take it seriously… These aren’t funny relationship questions. This isn’t a joke.

They’re serious relationship questions and are potentially make-or-break ones if you DON’T take them seriously! So try to go about it the best way possible, and it will all be okay…

Tough Relationship Questions

So now we’ve got an understanding about all of that, let’s get stuck in with these tough relationship questions, shall we?

Use these questions as ideas and inspiration for the tough relationship questions you may need to ask, or would benefit from asking.

Scroll through, take it all in, jot down any questions you like, and use it to expand on further – thinking of your own.

50 Tough Relationship Questions

In no particular order now then, here’s our 50 tough relationship questions…

1) Are you happy in this relationship?

2) How do I make you happy? What do you think makes me a good partner?

3) What things do I do, which don’t make you happy? How could I improve?

4) Where do you think we currently are, and do you think we’re on the same page with how / where we are?

5) Are you happy with where we currently are? Do you think the relationship has moved too fast, too slow, or just about right? How comfortable do you feel with all of this?

6) Do you think that you and I are truly compatible? And if so, in what ways?

7) In what ways do you think we bring out the best and worst in each other?

8) Do you think we’re connecting well, in all the different ways? Are you happy with both the physical and emotional intimacy that we share?

Do you and your boyfriend want the same things?

Let’s Keep Them Coming…

9) How do you think our relationship has changed (for better and for worse), since we first got together?

10) How do you think we, as individuals, have changed (for better and for worse), since we first got together?

11) Do you think your feelings are just as strong now, if not stronger, than they have always been? Why / why not?

12) How well do you think we deal with conflict, and communicate with each other about difficult things? And how well are we able to let things go in our relationship?

PSST, remember – it’s better to pick your battles wisely. Learn how to do this, and fully embed these new, healthy habits in your mind. [Click Here For Mastery!]

13) How well do we both, as individuals, deal with our emotions? 

14) What do you think causes the biggest issues and conflicts for us, in our relationship? And is this something that can be properly and permanently resolved? If so, how do you think we may best go about this? What things should we or could we try?

15) Are there any things you think we’ve said we’d work on but which we haven’t?

16) Is there anything that you’re holding onto, even to some degree, from a past conflict? Or anything that you can’t quite seem to fully let go of or get over?

Let’s talk about the things that are on the back of your mind so we can remove them completely! The last thing you want to realise is that he’s kind of forcing himself to love you now. You both deserve better than that! So…

RECOMMENDATION: Try This “Forgiving Others” Hypnosis if this is an issue in your relationship.

Tough Relationship Questions

17) How easy do you find it to forgive the mistakes I / we may make in relationships? And are there any things that you think are unforgivable? What’s your boundaries? What couldn’t you get past, or do you think a couple shouldn’t really get past? (Because it’s just too much!)

This is a pretty deep question to ask your boyfriend but these ones are needed!

18) What does a healthy and unhealthy relationship look like to you?

19) How have your past relationships influenced the way you are in our relationship today? These can be both romantic relationships, or the experiences you’ve had with friends / family.

20) Are there any things that you think or I should change, but you think won’t or can’t? And do you think these could get in the way of our relationship moving forward?

21) What things have we gotten through, which you’re proud of us for? And what do you think that shows us?

22) What’s the biggest relationship lesson you’ve learnt since being with me?

23) Is there anything you find scary about being in a relationship? Do you have any general relationship anxieties, worries or fears? How do you look at love and relationships, and what does it meant to you?

24) Where do you see us going in the next 2 – 5 – 10 years time? What are your key relationship milestones / expectations? Where would you like to see us? And how likely do you think it is that this will genuinely happen?

Things to talk to your partner about

You’re Doing Well…

25) How committed are you to this relationship? What would you, or wouldn’t you be willing to do to make it work?

26) Do you think we want the same things, at the same time? And is timing a concern for you at all?

27) Do you have any doubts, fears or concerns about us and our relationship? And how long have you felt this way? Plus (where relevant) where do you think they’re coming from and how valid really are they?

28) If you could change anything about our relationship, what would it be?

29) What do you love the most about me? Big things and little things. (Tough relationship questions can be positive ones, too you see. It can also be talking about the things you don’t tell the other person enough!)

30) Are there any things you wish we could talk about? But which you personally find hard to raise?

31) Or any things that you want to talk to me about, but which I make it difficult to do? (Because of relationship anxiety, excessive worry or toxic behaviour for example.)

32) What do you think have been some of our best and worst times to date?

Tough Relationship Questions

33) Do you think we fully understand each other? Let’s explore this further – how do you understand me, and what things do you think I perhaps don’t fully “get” about you, and the way in which you are?

34) Do you think we can read each other well? (You can actually go one step further and try this out by asking some hypothetical couples questions too!)

For example, when one person is feeling down – the other can tell, without them even needing to say. And if not – why not? Are they not paying enough attention or is the other person still closed off? Let’s talk all of this through.

(Note: you don’t need to be mind-readers, but you should care enough to be aware of these kind of things! Plus – the better you understand each other, the stronger you become.)

35) Do you think I pay enough interest to the things that are important to you? Or ask enough questions about you and what’s going on in your life?

36) Do you think the relationship ever feels one-sided, and that we’re both putting in the same effort and feel the same way? Do you ever feel that you or I aren’t getting our needs met? Or that one of us doesn’t feel as strongly?

37) What makes you feel close to me, and connected?

38) How do you like to give and receive love? What is your love language? And do I meet your needs when it comes to making you feel loved in our relationship? (It’s important you both understand this one and ask the more, intimate questions in a relationship.)

39) How about attachment styles? Do you think we have the same or different attachment styles and do you think this has an impact on our relationship at all, or the way that we are with each other?

Tough Relationship Questions

We’re Into The Final Set…

40) How do you feel about the relationship we have with each other’s friends and family? How well do you think we fit into each other lives? Is this working, or could it be improved on in any way?

41) Do you think we spend enough quality time together? Or, on the flip side, too much time together? Is the relationship too clingy or smothering?

42) Do you also feel like you can still do everything you want, aside from me? Have we got the balance right?

43) Have you lost yourself in any way, since being with me? Or noticed a change in how / who I am?

44) How much have you / we had to compromise in this relationship? And is that normal / healthy / an acceptable amount? Let’s discuss.

Tough Relationship Questions

45) Do you think we trust each other, and how strong is our trust? If our trust was ever broken – how well was it re-built? And what can we do to continue building on our trust and strengthening it, so we both feel completely happy and secure?

46) Do you ever feel like we take each other for granted? If so, how and when? (With this you could also do an Appreciation Exercise to recognise, there and then, how lucky you both are.)

47) Do you ever struggle with jealousy? In what kind of situations? And how do you deal with it? Is there also anything I could do to help with this? (After all, you are a team!)

[You can substitute many other words into this question to better understand any area. For example, if one of you is controlling, or insecure, or gets overwhelmed. There’s plenty of areas you can talk about here… There’s also plenty of ways to work on each of these things.]

48) Do you think we have seen each other at our best and worst? And what times were these?

49) If you could go back in time and change anything that’s happened in our relationship so far – would you change anything? If so, what and why? And what would you like us to learn from it from here?

50) … Do you have any questions you’d like to ask me? (The questions you choose to ask your partner should also prompt more / any from them too, you see.)

That’s All For This One

So there we have it – 50+ tough relationship questions, plus how to establish the kind of questions you may need to ask in your relationship, to further strengthen it.

Want to build on this further? Increase your confidence in how your partner feels?

Then there’s also this post with 50 Questions To Test Your Partner’s Love, or for more quick-fire tough relationship questions, try these 100 Essential Yes or No Questions For Couples.

Just be brave. Have confidence. And really open up your communication.

Remember – you can get through almost anything, as long as there’s openness, willingness and you put the work in!

Hope this helps. All the best.


Tough Relationship Questions
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Ella Stearn
Ell is a Breakup, Dating & Relationship Specialist & Coach, with over 3 million annual readers, globally. As the Creator of Forgetting Fairytales, her mission is to help you learn to love yourself, find the right person to give your love to, then make it a love that truly lasts.

3 thoughts on “50 Tough Relationship Questions”

  1. After being married for 25 years, I found this article especially insightful and helpful. Hubby and I have fallen into a rut, of sorts, and some of these questions really helped us re-center and I feel more secure in my relationship now. Some of them were tough to ask. I’ve made a list of others that I want us to discuss. Great article!

    • Thank you for commenting Jenn. I’m so glad you found it valuable and that you’re continuing to ask the tough questions that will only help and support your relationship. It’s perfectly normal to fall into a rut at times… 25 years is amazing! But I really hope these questions continue to help to bring you closer and feel more aligned again. Wishing you both all the very best. Love, Ell x

  2. My partner and I have been together for a few years now but there are still some things we haven’t talked about. I’m excited to bring these up and see where the conversation takes us. I know it will only help to strengthen our relationship, so thank you.


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