• Sarah Yoo

8 Uncomfortable Questions To Ask Your Partner To Take Your Relationship To The Next Level

Do you and your partner want to deepen your connection in your relationship?

According to a psychotherapist, Laura Dabney, nothing can progress in relationships unless it is built on a solid emotional foundation.

Asking the right questions is extremely crucial as it invites you both to be open and vulnerable with each other, which strengthens the emotional intimacy of your relationship.

So here are some uncomfortable questions you can ask your partner that will help to take your relationship to the next level.

Before you have this conversation with your partner though, I want to encourage you to remember two things:

1. Go into the conversation with an open heart and no judgments.

Shaming or judgment cannot exist in your conversations! Accept and welcome the things that are shared as they are and do your best to not take them personally!

2. Listen to Understand, not to respond

Don't react to their words by defending yourself. Listen to really understand them. Don't interrupt them. Just listen. Then, share your observations when they have finished.

Now that we got that out of the way, let's get into it!


1. What are you worried about in our relationship?

Have you had thoughts about us breaking up? If so, what are they?

You are opening up a safe space for you to both share thoughts you might have had but have been too scared to bring up. 

It's important to reassure each other by communicating that things that are shared in this conversation won't be taken personally and will be received with an open heart.

"I know that this is an uncomfortable topic - I just want you to know that whatever thoughts or feelings you've experienced is perfectly okay and I won't take it personally."

2. What are some things that I do or habits that I have that annoy you?

Most of us don't want to be honest about what we don't like about our partners because we don't want to hurt their feelings.

But it's worse to get annoyed or bothered every time your partner does something yet you don't communicate it to them.

HOW you communicate this is important.

Don't demand a change - no one has the right to demand a change in anyone. Remember that people are doing you a favor if they decide to make positive changes to benefit you in some way.

Instead, make a gentle and detached request and communicate it with a tone of appreciation.

"Hey, can I ask a favor? I noticed that the clothes are often left on the floor at the end of the day and although I enjoy helping, I would love it if you could help me by putting them in the laundry basket. It would make my night so much easier. Thanks for listening."
"Is there anything that I've done in the past that you'd prefer to be done differently?"

Following up your request with a question like above, opens up the space for them to share anything that might be on their mind. It helps to neutralize the pressure as you are acknowledging that it's not one-sided.


3. How do you want our relationship to be different from your parent's relationship?

How do you want it to be similar? 

Our fundamental understanding of romantic relationships has been created based on our perception of our parent's relationships.

We mostly learned about

- what it means to be a female/male in a relationship

- what love and intimacy looks like

- how to deal with conflicts

- how to treat our partners

- what we deserve to receive in love

by watching our parents.

So, a great way for you to understand your partner, even more, is by getting a deeper insight into what they saw and experienced growing up.

Get curious about your partner's upbringing:

  • What kind of relationship did their parents have?

  • How did they treat each other?

  • How did they overcome difficulties?

  • What values were important to them?

4. What kind of relationship did/do you have to the parent of the opposite sex (Female - with their dad. Male - with their mum)  How does this show up in our wants and needs in a relationship?

I've seen a pattern where our needs and wants from our relationships can be predicted from what we desired the most from the parent of the opposite sex.

For example, a former client's father was physically available but not emotionally available for my client. She grew up always wanting more of her father's emotional support. She later learned that this was also what she desired the most from her partner - she wanted to feel heard, safe and trust that her partner will always be there for her when she is emotionally struggling.

A deeper understanding of your partner's greatest needs and desires from a relationship means that whenever and wherever possible, you will be able to provide this for them.

This is not to say that you are solely responsible to meet their needs.

No one is responsible for anyone else but themselves.

But as a partner, it's important to put our best foot forward and do what we can to help and meet our needs of our partners to help them feel supported and loved.


5. How do you feel about your finances? 

Have a real conversation about money. Not just how much you make but talk about the relationship we each have to money.

Questions like below can help you kick-start this conversation:

  • Do you have resistance around earning or spending money? Why?

  • Do you feel uncomfortable asking for money? Receiving money? Why?

  • Do you have expectations on how we each contribute money as a couple?

  • What financial goal do you have?

Examine where these issues might come from for both of you and help each other develop a better relationship to money so you can prosper individually and as a unit.

6. Do you want to get married and/or have children? If so, what does that look like for you? 

Create a safe space for you to both share your future desires that require the contribution from your partner. Encourage them to be honest with themselves and therefore with you.

Even if it feels uncomfortable, keep asking specific questions to get really clear on what it looks like if your desires on marriage and children don't line up. 

Example of continuing to ask specific q's on one topic:

  • Do you want children?

  • If so, when? How many?

  • If not, what does this mean?

  • Is it a deal breaker for you if one of us want children but the others don't?

  • Are you saying you are okay with me not wanting children in hopes that I will change my mind in the future?


7. How comfortable are you in communicating your sexual wants and dislikes? 

This is a great warm-up question before the REAL questions:

  • What do you like/dislike in our sex life?

  • What do you want more of?

  • Is there anything that you've been wanting to try but have been uncomfortable to bring up?

8. What's something that you want to see more from me, that you find attractive?

Chances are, there are some things that you partner would love to see more from you that will increase his/her physical attraction to you.

Maybe he would love to see you in a bright red dress and matching lipstick one night.

Maybe he finds it irresistible when you spontaneously come for a passionate kiss at random times.

Maybe she finds it super hot when you get dressed up in a dress shirt and plan a romantic dinner date.

Maybe she loves it when you give her a loving kiss in front of her friends.

Remember, this isn't coming from an energy of "you must change to make me happy"

It's more about the gesture of wanting to do things that your partner likes.

It's more about maintaining that excitement and fire in your relationship, no matter how long you have been dating.