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30 Questions to Help If You Have Doubts About Your Relationship


“Your mind will answer most questions if you learn to relax and wait for the answer.” ~William S. Burroughs

One of the best life lessons I learned was from my beloved grandmother. She taught me to never be afraid to ask questions.

She would often look at me with her warm, almond-colored eyes and say, “The best way to learn, to gain clarity is to ask questions. Never take anything at face value.”

Even as an adult today, the truth of her wisdom continues to prove itself.

The beauty of constant questioning is that it is often the fastest path to enlightenment. It leads you to search for answers. It encourages you to be more proactive in your life.

When I was in college, I could only afford to visit my family during summer and Christmas breaks. While I was at home, I particularly enjoyed spending time with one dear friend. We had known each other since junior high school, and I considered her the younger sister I never had.

During my sophomore year in school, she contacted me and revealed she had romantic feelings for me. She wanted us to start dating.

I was completely caught off guard. I had no idea she felt this way. Sensing my conflict, she asked that I think about it, and said we would talk when I saw her that summer.

For the remainder of that semester, I agonized over what I should do. One night, my grandmother’s wisdom began echoing in my mind. What did I want?

Alone in my dorm room, I took a deep breath and asked myself very important questions that I needed to answer, but had been avoiding. Did I share the same feelings she had for me? Did I want us to begin dating?

By being still and questioning myself, I gained access to my inner voice, which I had been drowning out in my panic.

It revealed that while I did love her, I wasn’t in love with her. Pursuing a relationship primarily out of fear of losing her would have been unfair to both of us, and it would have caused us to not live in truth.

That summer was difficult. When I told her how I truly felt, she was understandably hurt. However, our friendship survived because we both realized we cared enough to be brutally honest with each other, and that is rare.

To this day, I sometimes wonder what would have happened if I didn’t heed grandmother’s wisdom, and had reacted out of fear instead of stopping to question my true feelings.

If you are having doubts about a relationship, please let me assure you the answers you seek are within you. You just may be allowing fear to muffle your inner voice.

The following are 30 questions that can help you achieve more clarity about your relationship—what’s working, what’s not, and why. Please keep in mind there are no wrong or right answers, just insightful ones:

1. Do you completely trust each other?

2. Do you believe in soul mates, and if so, do you believe you are each other’s?

3. When was the last time you said, “I love you?” If it’s been a while, why?

4. Are you satisfied with the intimacy you share?

5. How often do you laugh together?

6. Do you feel you have made personal sacrifices for your relationship, and have they been reciprocated?

7. When you think of your partner, do you smile?

8. Do you feel threatened when others find your partner attractive, and why?

9. Do you believe your partner is your biggest advocate?

10. How do you feel about your partner’s views on finances?

11. Do you enjoy spending time with your partner’s relatives? Friends?

12. Do either of you dredge up resentments in arguments, and why have you struggled to let them go?

13. How do you feel when your partner arrives home after being away?

14. Is your partner your best friend?

15. Is there a secret you are keeping that if your partner knew, you feel you would lose them?

16. Do you feel that your partner accepts you?

17. When did you realize you had fallen in love, and how do you feel when you think about it?

18. Have you seen each other at your best and worst?

19. Would you ever consider having an affair? Why? Why not?

20. Are you excited about your future together?

21. Do you feel your relationship is a true partnership?

22. When was your last romantic outing?

23. Does it bother you if your partner has friends of the opposite sex, and why?

24. Do you accept each other’s belief systems?

25. When was the last time you talked about your future together, and were you on the same page?

26. Do you feel as if you can communicate without saying a word?

27. What is your happiest memory of your time together? Your worst? Are there more happy memories than unhappy ones?

28. What is a relationship deal breaker for you, and have you overlooked one in this relationship?

29. How do you feel about the last, in-depth conversation you and your partner had?

30. Do you show your love for each other often, and if not, why?

If you are seeking clarity about your relationship, the best source of insight is from within. You just need to be unafraid to ask for the answers you seek. Then trust those answers and yourself.

Wishing you much love and success!

Photo by Björn Söderqvist

Avatar of Terez Williamson

About Terez Williamson

Terez Williamson is the founder of Smartly Smitten, where he shares relationship advice centered around self-love and respect. He is also the author of the ebook Minimalism and Relationships: Consume Less, Love More. You can follow Terez on twitter at terez07.

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  • Adrianna

    Great post! It helped me realize a lot of things. Thank you!

  • Lisa

    This is great, and so helpful! (I especially appreciate that it was written by a man. :))
    With every question answered, I had an immediate and bright response. Thank you.

  • Aditya Krishnan

    Great! thanks

  • http://www.smartlysmitten.blogspot.Com/ Terez

    Lisa, I’m so glad you found these questions helpful. Thank you for your kind words! :)

  • http://www.smartlysmitten.blogspot.Com/ Terez

    Glad you enjoyed it Aditya!

  • http://www.smartlysmitten.blogspot.Com/ Terez

    You are most welcome Adrianna. Thanks for taking your time to read it!

  • Jessica W. Noujeim

    This was such a useful and enlightening read, Terez. I will be saving it and have passed it on to many friends. Please continue to share your insights with us!

  • http://www.smartlysmitten.blogspot.Com/ Terez

    Thanks Jessica!

  • lv2terp

    GREAT post, with wonderful wisdom, and wonderful questions to ask! :)

  • http://www.smartlysmitten.blogspot.Com/ Terez

    Thank you!

  • Marissa Walter

    I love this. A wonderful way to take stock of your relationship and help both people to grow. Thank you!

  • http://www.smartlysmitten.blogspot.Com/ Terez

    I’m really happy you found the article of value Marissa!

  • LaShanda Velez

    I really really liked this. Your questions allowed me to think about my past relationship & If I should consider going back. But based on how I answered the questions, I dont think he is the one for me… Will use these questions in the future if I ever date again.

  • Work In Progress

    It’s a great compliment to your partner to be choosing your relationship instead of needing it.

    It takes a lot of courage to ask the kinds of questions you pose. But when you let yourself think about these things, you feel a sense of peace and integrity even if you don’t like the answers.

    I’m glad your friend valued your friendship enough to maintain it even though it didn’t go in a romantic direction.

  • Cj Emanuel

    These are great questions to ask your Self at any time in your relationship. You don’t have to wait until doubts creep in. Thanks for sharing, brother.

  • http://www.smartlysmitten.blogspot.Com/ Terez

    LaShanda, when it comes to a past relationship which wasn’t the best for us, it’s often hard to let go because it was familiar. I applaud your courage in moving forward with your life. I’m especially thrilled if my article played some small part in helping. Thanks for reading and sharing!

  • http://www.smartlysmitten.blogspot.Com/ Terez

    I couldn’t agree more that when you gather your courage to face the truth of your circumstance, peace and direction inevitably follow. Thanks for your perspective WIP! :)

  • http://www.smartlysmitten.blogspot.Com/ Terez

    CJ, excellent point about not waiting until your relationship is in crisis before assessing its health! I really appreciate your comment. Thanks for reading man.

  • adi purplishchic

    I have been struggling to let my last relationship go. This article really helped with that. I thank you, even though a simple thank you is not enough.

  • ck

    These questions were interesting… Is it possible to have a successful relationship without necessarily being able to answer all of these questions in a way that is “deep” or the “obvious answer”, in your opinion? (i.e. I don’t believe in one soulmate and I don’t think my partner believes in soulmates at all, or we don’t say “I love you” all the time, but it doesn’t necessarily mean we don’t feel it…)

  • http://www.smartlysmitten.blogspot.Com/ Terez

    Hi CK! These questions are meant to inspire introspection. There are no right, wrong, or obvious answers – just ones meaningful to you and your unique circumstance.

  • http://www.smartlysmitten.blogspot.Com/ Terez

    Adi, the fact you found the article of benefit is thanks enough. I wish you all the best!

  • stonefree

    This is a great post, and I think it is useful for people at any stage in a relationship – starting one, in the middle or letting go. It seems you have inherited your grandmother’s wisdom, and I will definitely be checking out your website. Thank you for sharing!

  • http://www.smartlysmitten.blogspot.Com/ Terez

    Thank you for your kind compliment!

  • Jasmine

    I was moved when I read some of the questions, they were all positive answers and they made me smile, except some that I realised were completely to do with me and my own securities and have nothing to do with my boyfriend or the way he acts. I realise more that it is me that needs to work on myself and my anxiety and that we have a loving and beautiful relationship.

  • Kaveri s

    yes .. these questions are very helpful. When i answered those question i realized that i need to more confident about my relationship. I need to be loyal and truthful towards him..
    Thanks alot.

  • Brittany

    Thank you for writing this Terez. I’ve been deeply dependent on my relationship due to my lack of self love. Holding on for dear life to his light, hoping it will drag me out of my darkness. But if I love him like I truly feel I do, I wouldn’t do that to him… but now he is just as equally dependent on me. His father(best one I’ve ever known) died and his family completely fell apart. So here we are, equally dependent, equally weak and equally sad.. We justify staying together by knowing that great relationships are built not found. You don’t run away when things get tough, you stick through it and learn from it. So I’ve basically been driving myself mad… do I listen to my heart screaming at me to be alone, even if that means going back to my depressing mom’s house, or do I stick it out and work on our issues and grow? I have no idea. I can’t seem to find an answer. But I do know that it is fear that is keeping me from leaving and it’s also fear that’s making me stay. And I do know that pretty much every answer to those questions is not in favor of us staying. But god damn, that boy is an angel. Maybe really, I just want to leave in hopes of the big PUSH that comes from a break up. It’ll push us both to be better. But in order for that to work he’d have to think that I don’t want to be with him ever again. Do you see why I’m going crazy?

  • Kim

    I thought this was awesome. I’m at a crossroads in my relationship and #28, the deal breaker question, struck me. The deal breaker has happened on 3 separate occasions and I still stayed. Now my heart is telling me to go forward in my life and I’m listening. Thanks Terez

  • Janelle D

    I enjoyed this post very much. I’ve been wanting a deeper connection with my love lately and I think that reflecting on these questions will open the possibility for some interesting discussions. Thank you!



  • Jenna

    Do you believe your partner has to be your soul mate? I met another man who I believe is my soul mate while I am still dating my partner. Although we are just friends and I don’t really feel attracted to him this has caused me much anxiety because of societies perceptions of relationships and soul mates. This other guy is like a soul mate in the way we think about the world exactly the same. However, I still feel so at one with my partner and he makes me feel the happiest I have ever been, but I still have doubts sometimes. I think of my partner and I as like Yin and Yang, although we are different we balance each other out with the traits the other lacks to become a whole. I try to listen to my inner voice as you say and usually it tells me to stay with my partner, but meddling thoughts about this other potential soul mate man seem to always return which makes me feel guilty and anxious. What do you think?

  • Jessie

    Have you decided what to do yet? :/

  • christien

    I need some advice im with ma boyfriend i love him alot and he tells me the same thing but he have a girl at his job dat reallu likes him and they been texting alot and he been making excuses to go see her i wanna fight for him but do u think im wasting ma time cause i told him about it and he said he dont wanna lose either im lost please help

  • Iris

    Thank you for this list of questions…I needed them more than I knew. I was able to pull the answers from within and banish the doubt within myself. Love to you and your smart grandmother! She would be/must be so proud to have a grandson so in touch with himself and the divine possibilities within ourselves…

  • john

    can I ask my girlfriend to stop shine away from me when she’s checking Facebook or any messages is it okay to ask

  • Lisa

    I have been struggling with my “inner voice” for about a year now, and find myself living comfortably in an uncomfortable life. These questions helped me focus on what seems to be an inner conflict between my head and my heart. My conflict with my husband continues and lack of any resolution on my part is because I often think of him or my daughter before myself and what I deserve. Most of my answers to these questions were NO. Do you have additional resources to recommend for help once the realization is made that the relationship is a source of much unhappiness rather than love and happiness?

  • http://www.smartlysmitten.blogspot.Com/ Terez

    Hi Lisa. My best piece of advice for you (and hopefully your spouse) is to seek out counsel from a professional marriage counselor or therapist, who can help you further identity and confront the specific issues you face in your relationship. Good luck to you.

  • http://www.smartlysmitten.blogspot.Com/ Terez

    Hi John. You didn’t provide many details, but the best way to broach this subject with your girlfriend is at a moment when she isn’t distracted by Facebook or social media. Gently let her know you are feeling neglected – but do not place blame or make accusations. Doing so is counter-productive and will only make her defensive. Good luck!

  • http://www.smartlysmitten.blogspot.Com/ Terez

    Thank you for your kinds words Iris. Sending much love and light to you as well!

  • http://www.smartlysmitten.blogspot.Com/ Terez

    Hi Christien. You are in a difficult position, but the bottom line is: your boyfriend doesn’t seem ready to commit to one person. It seems you both are at different places in your life emotionally. It’s no one’s fault, this is something that just happens. However, don’t do yourself a disservice by clinging to a relationship that isn’t right for you. Though it’s difficult, let go. This way you are making room in your life for the kind of relationship you desire – and deserve. Good luck.

  • http://www.smartlysmitten.blogspot.Com/ Terez

    Hi Jenna, My apologies for such a late response – and I hope you found the resolution you needed. But just in case, the fact is, you will always find others you will be attracted to – that ‘s human nature. However, when those thoughts enter your mind. Sit down and review why you are with your current partner. What is it you love about them? What are their admirable qualities? Are you willing to let go of your present relationship to pursue another – and what will be the cost to you if you do this? These are important questions to ask .

  • http://www.smartlysmitten.blogspot.Com/ Terez

    I’m so glad you found the article helpful Talziano! All the best to you!

  • http://www.smartlysmitten.blogspot.Com/ Terez

    So glad you found the article of help Kim. Good luck to you!

  • http://www.smartlysmitten.blogspot.Com/ Terez

    Hi Brittany, I know it’s six months later, and I hope you found peace and a resolution to your situation. Just know that when we make decisions out of fear, we are often circumventing creating a better circumstance for ourselves. Bottom line co-dependency isn’t love. My advice to you is to seek out the services of a therapist who can help you identify why you are staying in a relationship that is doing the opposite of empowering and edifying you. Good luck.

  • http://www.smartlysmitten.blogspot.Com/ Terez

    So glad you found the article of help Kaveri. Good luck to you!

  • Bhumika Nice19

    I met a boy in my college, he’s a cool friend to hang out with. I sort of like him( I have, Doubt). I don’t know he likes me or not (he likes me as a friend, but as a lover, I’m not sure). I gave a hint to him that I like him ( he totally gets it), but if he agrees, should I peruse this relationship???

  • Alex

    My girlfriend is rude or bossy at all, but sometimes I doubt whether it’s really right. We’re fairly different and she doesn’t really enjoy my type of humor. We’ve been together a year and a half and for the last half a year part of me has longed for more in my life. I would compromise a lot for her but there’s only been two things I’ve really asked of her. They weren’t big but because I was so attached I put up with her oblivious and hurtful nature, even if those two things that took her so long to compromise are borderline deal breakers for me. I find myself being told off a lot and being frustrated when I really shouldn’t be. I know that I am part of the problem, but I can’t seem to fix it no matter how hard I try. If she can’t fill my emptiness or ever really do anything impressive or console me and I end up being bitter quite often, then I should clearly move on right? Our sex drives are vastly different which has stressed me a fair bit in past too. I think that maybe I would be better off on my own, but I’m just waiting for something to give me that final push. I’m so attached and I think that’s what’s holding me back. What do I do?

  • alex

    not rude*

  • laurose

    I am trying so hard to figure out what to do in my current relationship and even though I find myself saying “yes” to many of these questions I still don’t know what to do… This is so frustrating

  • Jen Haggerty

    These are questions I need to ask myself after a turbulent couple of weeks. I will revisit them in one month and if I feel the same, I will have my answer. Thank you

  • William Tyson

    Where do I find the answers to these questions?

  • amber lavigne

    used some questions :) helped me figure out things with my bf :)

  • shaghayegh

    me and my bf were best friends at first then became lovers ….thr r times i feel crazy for him and then thr comes times i feel not so special,he is a very very nice man and the best personality…i don’t know y is it like this,i’m afraid i might hurt him:(

  • Vivian Wyane

    Contact,for any kind of problem you think that there will not be a solution i promise you that you will be a living testimony just give a try to him okay
    he do it for me,and i have a strong believe that he will also do it for you…contact him now….(

  • Cass

    This is amazing.