12 Challenging Questions to Ask in a Romantic Relationship

12 Challenging Questions to Ask in a Romantic Relationship

What are the fundamental questions to ask yourself if you want to know whether you are in a healthy, dynamic and resilient relationship? What are the most important questions to get to know someone?

I want to share with you the 12 questions I’ve seen work that draw out key conversations that catalyze insight into finding these answers. 

This insight is derived from  {THE AND} Project in which my team and I at The Skin Deep hosted over a thousand conversations between people over the last 8 years in the endeavor of building a library of human connection. These are deep questions to ask that I’ve seen work time and time again, regardless of sexual expression, polyamorous or monogamous, queer or not, new or long term. 

These 12 challenging relationship questions I recommend you ask yourself and your partner to see if you're getting the most from it and if you're giving the most to it. 

Throughout I will link to conversations we have hosted in {THE AND} so you can see how other couples processed these get to know you questions, as well as other inspiring resources. 

1. What are three memories you treasure most with the other person? 

Ultimately romantic partners are people you walk the path of life with, and as you walk that path no matter how short or long, you create memories - you share an experience. 

Are you consciously aware that you are creating and building memories?

At the end of the day in this game of life, no one gets out alive. So what are the memories you're creating together? And how much do you treasure them?


2. What was your first impression of the other person and how has that changed over time?

Oftentimes, we fall in love with that first impression, that first story we created of who the other person is. And the rest of the relationship is an effort and a challenge to that original story that drew you in. 

It's almost like that first impression is the anchor of which we then pull and press against as we embark and change over time. 

That first story that attracts us is lasting, for better or for worse. 

So what is your first story of who this other person is and how is that changing for you over time as you're with them?

Here’s an example that illuminates a shifting worth noting that may sound familiar to you. In the beginning of a relationship, your partner tells you an anecdote, something about them. 

Six months later, they tell you that same thing again. 

And you might think “well, I've already heard that, you're just repeating it.”

Yes, indeed, you have, but the meaning of the anecdote has changed because your understanding of the person has too. 

The first time you heard the story, you knew this person for three months. You understood them to some degree. 

A year or two later, you hear that same story again, however details of the anecdote present themselves that weren’t there before because your understanding of your partner has deepened. 

So your first impression of someone is the thing that locks you in, but your relation to that impression can change over time. Are you cognizant of that? 

Are you riding the wave of change in perception of the person you are with? Are you constantly rediscovering them anew? 

I’ve noticed that in vibrant romantic relationships, participants are conscious of the ever changing person they are with by being present to the constant discovering of the other. 

3. What are you hesitant to tell them about? 

Let’s face it. There's always something you are hesitant to talk about. Or to ask your partner

And that is most likely what you should talk about. 

Because where there is tension, where there is hesitation, is most likely the greatest fodder for growth. 

If you're really going to build a long lasting, strong, deep romance, you've got to get good at  leaning into the conflict. You've got to lean into the places that are uncomfortable because that is where the greatest opportunities for growth exist. 

And I have noticed that if you do not, then at some point, something happens that requires you to face it and it becomes much more difficult to handle. 

It’s like stretching. If you stretch every day, lean into the pain a bit, you are less likely to pull a hamstring and be out for a week. 


4. What’s the pain in them you wish you could heal? 

A key part about being in a relationship is that you see the other from different angles that they don't see for themselves. 

And even though you are not them, you're integrating with them to such a level that their pain is your pain. Your pain is their pain. 

Even though you wish you could, you can't heal them. Only they can heal themselves.

What you can do however is support them in the healing process.  

Are you able to do that? Are you able to communicate that you are there for them as they walk their journey in their own healing? 

Can you create the space and patience for their journey even if it's not the pace or the method that you would pursue yourself? 

And the fifth question is the flip side of that.


5. What’s the pain in you, you wish they could heal? 

Sometimes we find ourselves in a relationship because we are hoping the other person can give us what we aren’t able to give to ourselves. 

We consciously or unconsciously find a partner that can fill a void, that can do something we cannot, that offers something we feel we cannot.

They can't heal you. Only you can heal yourself. But they can support you in your healing. 

How are you supporting them in their support of you? Are you articulating the pain you experience? Are you hiding it? Are you open to being helped? Are you leaning into the discomfort that sometimes healing requires? 

A relationship is a profound engagement of two souls who are sharing their journeys as they strive to evolve through their relation with the other. 

So what expectations do you place on the other that cannot be met? And how much responsibility do you take in fully participating in this journey?


6. What’s one experience you wish you never had as a couple and why? 

Maybe you can be in a place where you understand that even though that was a painful experience you wish you never had, you appreciate the gifts that came from it. 

This indicates a very resilient relationship that is making the most of what it is going through. 

Are you choosing to face even the most challenging obstacles together and reaping the lessons from it? 

Harnessing conflict into growth and pain into deepening, is a clear harbinger of resilience in a relationship.  


7. When was the last time you considered leaving the relationship and why didn’t you?

This often happens in long term relationships but also for some in the early stages of one as you consider whether you want to commit or not.

It is the opportunity costs of what other possibilities exist for you against why you are staying in the current situation. 

The longer you are in the relationship or the more conflict you have, the more this question may come up for you. Or for those newer relationships, your awareness that committing may close other opportunities sparks this question. So it is a real check in. 

How heavy is the consideration for you to leave and why are you staying in it? 

Are you staying in it because there are so many positive things, and even though there may be challenges, it is a catalyst for growth for you to evolve independently as well as together as a couple?  

Or are you staying in the relationship because you're scared to leave it? You’re scared to be alone or fear that there is nothing better out there for you? 

This is a profound gut check, a question we don’t like to ask.

But if you find yourself leaning into ‘I know this is challenging but I'm getting so much out of it and I'm growing.’ A good reason to stay. 

If on the other hand, you feel that yes, you've considered leaving many times and you're just scared to go. Then maybe indeed it's time to leave. 


8. What is your greatest challenge together and how are you addressing it?

Every relationship has its challenges. No doubt about it. 

If you don't have challenges it’s because you're not growing. You're not changing. You may be avoiding conflict. You may be staying in the comfort zone. But we don’t grow in comfort, we grow in discomfort. 

So what is your greatest challenge? And more importantly, how are you addressing it? 

The courage to face challenges and handle them in a constructive manner is the key to a healthy relationship. It’s not the avoidance of conflict that makes us resilient, it's the ability to handle it constructively that speaks volumes to the resilience and dynamism of a relationship. 


9. What are you learning from them? 

What are they teaching you? How are they changing you? 

A Relationship is an opportunity for a soul to evolve through the sharing and the reflection in the engagement with another soul.

So what are you learning? And if you're not learning anything, then either there's not enough juice in the relationship. Or you're not cognizant of what you're learning. 

Are you paying attention to the lessons your partner is offering you? 


10. When do they inspire you most? 

What do they do that lights you up? How do they ignite the desire in you to be a better version of yourself? 

What do they do that reminds you just how amazing and unique they are?

Are you noticing these things? More importantly, do you let them know when they are? 

Regularity breeds comfort which may lead to a lack of gratitude and acknowledgement. 

Paying attention to what is incredible about your partner feeds the practice of gratitude. 

Acknowledging them for being who they are and how that inspires you gives the present a sense of eternity.


11. What are you most excited about for your future together?

As you recall the first two questions to ask your partner were about the past; the first time you met, and the memories you have created together. 

Now let's talk about the future here; what are the memories you will create together? 

What is pulling you both forward? What are you most excited about building together?

What does the horizon look like? 

A compelling story for the future is reason enough to continue on the path of a relationship. So let’s make sure there is one. 


12. Why do you love them?  

This question encapsulates all the previous eleven questions. If there is something you missed, you could voice it here. 

Another nuanced albeit different version of this question is, What Do you Love them For? 

What’s most important here is articulating it to yourself and to them. 

Furthermore, how often do we really get the chance to let the other person know what their love feels like? 

And how often do you articulate it to yourself; to remind yourself of the divinity of the other and the relationship you have with them? 

Being fully present in a relationship, when it's great and especially when it's hard, is the greatest gift you can give yourself because a relationship amplifies your life experience. 

Walk the path together fully present, reminding yourself of the lessons you learn through your common challenges, and the offering of growth will be ever present. 

I hope these 12 questions to explore your  love support you in that effort.

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