30 Important Questions to Ask Before we Commit to a Relationship.

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This morning, I read an article that highlighted the reasons people find themselves; or perhaps lose themselves in relationships that are not a good fit.

I noticed myself nodding in recognition as I ticked off the kinds of issues that clients I have seen as a therapist for the past three decades have presented in our sessions. They range from not knowing the person in the mirror well enough to being disillusioned by the person on the other side of the bed.

While it would be easy to maintain my professional objectivity, what remains with me that is fodder for this post is how deeply and profoundly the concepts presented touch on my own journey.

Married at 28, with a history of multiple relationships prior, widowed at 40, following a 12 year “paradoxical marriage,” I have been ostensibly single for nearly 16 years, with the exception of a few short term relationships and friends with benefits interactions.

I could chalk it up to fear of loss and re-creating the worst dynamics of my marriage, analysis paralysis about what I did that contributed to some of the dysfunction in that decade plus two, regret and shame about some of my choices, raising my son as a single parent, experimenting with relationship paradigm options, re-inventing myself, busy-ness with life stuff, focusing on career building and at times, truly enjoying being single and now that my son is an adult, making choices that primarily affect only me.

I could second guess “If I knew then what I know now,” and beat myself up over all of the shoulda woulda coulda’s and believe me, I have.

I would much rather explore and examine, from the perspective of being on the other side of the experience, not just what I want, but what I don’t want, even though relationship experts generally encourage focus on the positive. I am a believer, based on my own personal and professional perspective that I need to clear the detritus of previous encounters in order to build anew.

So many people create new relationships on the wreckage of old interactions. As Joe Jackson sagely says “You can’t get what you want, til you know what you want.”

There are questions I didn’t ask myself in earlier years, both pre and post-marriage and conversations that I wish I had back then. Of course this seasoned woman has had time and life enough to make these queries. Perhaps they would be helpful for you as well.

What do I truly want in a relationship? 

Not what someone else thinks it should be. Not family, friends or society. I’ll live with myself 24/7 for the rest of my life and if I choose to blend my life with another’s, that is crucial. My vivid imagination conjures up images of a dynamic, ever-growing “third entity” that combines the sum of the parts of the two of us.

At this point in my life, I have accumulated experiences and life lessons that I desire to share with a partner. I consider myself a wealthy woman since my friends and family are my treasures. The other person has “been there, done that, got the t-shirt” too. Together, we share the wealth.

How do I define relationship?

My current definition involves two people who have a common and merged vision, who communicate it openly and who take steps daily to strengthen and support that bond. As a minister who has married over 300 couples since 1999, I have witnessed this dynamic with many of them. Although my parents came from “different sides of the track,” with divergent socio-economic background, love and that intention sustained their nearly 52 year marriage.

A huge dose of love, fun, affection in word and action, co-creating wonder, thinking of the other person and what will delight them, shared responsibility for maintaining a household,  flexibility, willingness to work through “stuff” when things get messy, taking time and space to breathe and respond, rather than react and attack, knowing that we have each other’s backs, open mindedness and openheartedness, creativity, play, spiritual practice, sexual nourishment, mutual support of each other’s dreams (even if they are not in lock step with each others’), are on my desire list.

What am I unwilling to accept? 

Control, abuse, addiction, emotional manipulation, my own co-dependent tendencies taking hold, selling my soul for love, financial irresponsibility, lying, expectation that I act as caregiver and primary emotional strength in the relationship and that I clean up the “messes,” literally or symbolically.

It’s my take that relationship breakdown has a better chance of occurring because we don’t ask certain questions from the get-go and instead, make assumptions that love is enough to sustain it. This isn’t necessarily so.

The questions to ask if you are face to face with a prospective partner and if asked of you, to be answered with naked honesty:

What models did you have for loving relationships when you were growing up?

What did you learn from them and what did you learn from those that weren’t healthy?

What did you learn about self love?

How was love expressed in your childhood?

If you were a survivor of abuse, how have you done your healing work?

If addiction was present in your family, how has it impacted on you?

How do you want your relationship to mirror that of your parents and how do you want it to differ?

If someone disagrees with you, how do you face it?

When things don’t go the way you want, how do you handle disappointment?

How do you express emotion, most especially anger?

What was the best thing that ever happened in your life?

What was the worst thing that ever happened in your life?

How do you deal with change?

What brings you joy and satisfaction?

What are your values—particularly social?

How do you take care of yourself physically, emotionally, mentally and spiritually?

What is your take on child raising when it comes to discipline and consequences?

How do you face loss?

When the inevitable dark nights of the soul occur, what sustains you until the morning comes?

What are your spiritual beliefs?  (For some who see themselves as atheist or agnostic, what enlightens and enlivens you and from where do you get your sustenance?)

Let’s talk about our sexual desires, experiences and needs.

I am a big believer in full disclosure; knowing that there is a difference between secrecy and privacy. Without necessarily disclosing the names of all previous lovers and interactions, it is important that a partner know if there are others still in your life. Safer sex practices are crucial as well.

If you were in a committed relationship that shifted, how has your heart healed and are you ready for a new one?

Do you remain friends with former partners? (By the way, I see that as a strength if the friendships are healthy and not fraught with jealousy and manipulation.)

How do you balance needs for “we time” and “me time,” so that you nourish yourself as well as the relationship?

How do you use your resources…saver, spender, sharer with money, time and energy?

Do you want a relationship, or do you need a relationship?

Who are you without one?

Of course, these are inquiries that take place over time and not all at once on a first date. The professional interviewer in me laughs at the Ally Mc Beal internal dialog absurdity of that scenario.



What’s the Most Important Question We Ask? ~ Jake Eagle

Read this Before any First Date.

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Author: Edie Weinstein

Editor: Catherine Monkman

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Edie Weinstein

Edie Weinstein (Bliss Mistress) is a work in progress who learns daily from all of her relationships, a colorfully creative journalist, dynamic motivational speaker, interfaith minister, licensed social worker, Bliss coach and PR Goddess. She is the author of The Bliss Mistress Guide To Transforming the Ordinary Into the Extraordinary. Connect with Edie at her website.

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anonymous Dec 17, 2015 7:11am

Just what I am needing right now! My husband took his own life 8 months ago, for a number of reasons. I have a 23 year old, and a 14 year-old son. I have recently started seeing someone that I think I could share my life with – he has been divorced for 7 years and has two daughters, 12 and 16. We are ready to take our relationship seriously, and told our respective children. His daughters were thrilled. I have since met them and my youngest son has spent the last school holiday with them. They got along very well. My eldest son has started pulling rank and telling me that I am not thinking about my youngest son, and that I am thinking selfishly of only myself. I have dealt with my late husbands death (I saw a grief councillor, and I spoke to all our friends and family and anyone who would listen, ad nauseum. I have dealt with it. My son refuses to go for councelling, and said that if i continue to see this person, I will lose him as a son. (His father used to use threatening behaviour with me, when I disagreed with him.) My younger son is happy with my prospective partner, and I am respectful and aware of the effects of having multiple partners coming through my front door, (and bed). How do I deal with my eldest son. He has been phoning my family and friends, and has got everyone jumping to conclusions and discussing my private life without knowing all the facts. I am 49 years old, and have always been very responsible, and I am not impulsive. I am going into this with my eyes wide open. Why cannot people understand that one can find happiness again, even if it has come so quickly? How do I make this easier for everyone, even though it really has nothing to do with any of them. How do I do it with diplomacy so as not to alienate anyone either???

anonymous Jun 10, 2015 11:54am

I don’t agree with the article. All it takes is for two people to be committed to loving each other (with faults) and growing together … one day at a time.

    anonymous Jul 10, 2015 11:24am

    Had I known some of what I was getting myself into prior to certain relationships, I would either have been better prepared or would have refrained from getting into them in the first place. Not all relationships are healthy to stay in even if love is present.

    anonymous Aug 4, 2015 11:16am

    I agree with you – Every relationship teaches us something, even the really bad ones. We just have to see it, learn from it, discover things about ourselves we didn't know before. Real love is a choice. Two people growing together and choosing to love one another through thick and thin. If both parties have differences that do not hurt the other, but simply define who they are, to love them because of that is what it's all about. I do not expect my significant other to answer these questions the way I would, if there is a similarity, great, if not, even better. I've been in a relationship that mirrored me, it was empty after the "fascination phase." The best relationship I've ever been in is the current, and we definitely don't agree on everything. But in his words "Why do people feel they have to agree to work it out?" Honestly, I love than my man chooses to be with me like this, acceptance for who I am is the best, and the answers to these questions I learn as we grown together. Besides, we've both done things in the past we aren't proud of, but that doesn't define who we are now, together.

anonymous May 24, 2015 4:43pm

Hi Lex:

Thanks for your comment. On a scale of 1-10, how much do you matter to yourself? Were you, like many people, taught to put others first, as if somehow that makes you more virtuous, loveable and just plain simply, a better person? I use the analogy of flying on the airplane and when we are told what to do if the oxygen mask comes down, we instinctively think we are to put it on someone else first. In reality, you can't put someone else's mask on if you are passed out from oxygen deprivation. You can't fill someone else's cup if yours is empty. Often we attempt to give from a place of depletion. I know that I did for many years.

What is your ideal you like? Is it in synch at all with his? Would it be a departure from your own vision for yourself. Perhaps you could make a list of the qualities and values you already possess and then another of what he wanted of/for you. Good for you for taking care of yourself. Pain is sometimes a part of letting go. Not the easiest part, of course.

Here is a recent article I wrote for Elephant Journal that may help you heal. http://www.elephantjournal.com/2015/05/a-letter-to-the-l...

Many blessings,


anonymous May 22, 2015 7:00am

i just broke off a 4 month relationship with the perfect guy. For the first time I listened to my intuition and went with my gut. He was recently divorced. My divorce 1 yr ago. Both long-term marriages.

I felt he was trying to mold he into his ideal. Too much too soon. Too fast for me. It felt suffocating but he thought not. I chose to end it now rather than let it go on longer.

I feel horrible about causing him pain. My new realization is why is it hard to put myself first?

anonymous Mar 23, 2015 12:43pm

This is a great article and very timely for me, as I have a first date on Saturday. 🙂 This is someone I've known since high school, but we've just reconnected. We ran into each other the other night and spent hours just talking, which lead to him asking me on an actual date. Being divorced for 3 years and having just ended a very dead relationship a few months back, I feel like there is nothing wrong with being very straightforward with what I am looking for and what I am unwilling to accept in a partner. All that to say, that I am still very excited at the possibility of where this could go. And I appreciate your list of questions. It's also made me put some thought into what my answers to those same questions would be. Thank you.

    anonymous Apr 1, 2015 5:46pm

    My pleasure. So, how did the date go? Enjoy the journey.

anonymous Mar 12, 2015 6:57pm

Very/very interesting,bcos learning make's the wise wiser & the fools more foolish.

    anonymous Apr 1, 2015 5:46pm

    That's one way to look at it. (: Glad it drew your attention.

anonymous Mar 9, 2015 4:51pm

Awesome! Just what I was looking 4! Thanx!

    anonymous Mar 10, 2015 6:41am

    My pleasure. Glad it reached you. Feel free to share if you feel it would resonate with others in your circles. Wondering how it resonates in your life.

anonymous Dec 29, 2014 7:24pm

Thank you, Tara. It does take time to get to know someone and when questions are asked and answered honestly and with the intent to learn more about each other, then the experience is even richer and more fulfilling.

anonymous Dec 24, 2014 1:14am

Really insightful. Most people will not likely to take the time to fully articulate their responses but none the less it really points to some important aspects of character and personality that dictate how a partner will "show up". Thanks for sharing.

    anonymous Dec 28, 2014 6:03pm

    My pleasure, Tara. If you want to know how someone sees the world, it helps to know the questions to ask.

anonymous Dec 23, 2014 1:12am

Honestly the most ridiculous list I've ever read. Sorry Edie, I get your good intentions. Truly.
But some things on your list can't be answered. It has to be felt, demonstrated, experienced. One's heart reveals itself in actions.
Nonetheless, if people find this helpful, then that is great.
I'd encourage them to listen to their heart and truly connect with the other person. They will get the answers they seek.

anonymous Dec 23, 2014 1:11am

Honestly the most ridiculous list I’ve ever read. Sorry Edie, I get your good intentions. Truly.

But some things on your list can’t be answered. It has to be felt, demonstrated, experienced. One’s heart reveals itself in actions.

Nonetheless, if people find this helpful, then that is great.

I’d encourage them to listen to their heart and truly connect with the other person. They will get the answers they seek.

    anonymous Dec 28, 2014 6:02pm

    What would you suggest asking? These are questions I wish I had asked prior to getting deeply involved. These are questions that clients wish they had asked of partners as well. As I mentioned, they are not intended to be asked all at once. I am open to hearing your ideas, Renee. Feel free to share.

    People don't always reveal their truth before damage can be done. People sometimes settle for less than what they desire, because they don't know what to ask. As much as I tap into intuition, some answers come as a result of open hearted dialog.

anonymous Dec 12, 2014 5:13pm

Thanks Edie for a thought-provoking article. I too have decided to leave my marriage cause it was killing my soul alive. Now im in the horrible process of divorce trying to stay sane and minimize the damage to my two little kids. I don’t really hate my ex husband, but the hurt I feel is so deep it physically hurts. I left my home, family, job, friends and country for him and put aside my career for his and to have my children, and i never complained. But now, when the time came to split the property…, he ridicules me for being a housewife, for being provided by him, and needing spousal maintenance until i get to a place where i can work in my profession… AND He’s doing that by comparing me to his new girlfriend… I’m not playing the victim. I know the lessons i had to learn by going through the marriage and the divorce now are only for my own betterment. I know this too shall pass. Your question “when the emotional dark night comes, what sustains you till dawn?” Was a good one for me. Im trying to connect with my higher power and find acceptance, courage and peace through spiritual work from Al-Anon, Jeff Brown (im a fan 🙂 watched Karmageddon and read Soulshaping) and many more. I guess im feeling the unavoidable pain that exists between knowing and living certain truths. Any word of encouragement from you guys would mean a lot to me. Thanks again.

    anonymous Dec 12, 2014 8:29pm


    Bless you for taking care of yourself and your children in so many ways. You are nourishing the wounds so that they will heal. When I hear stories like yours, I feel anger that anyone feels they have the right to demean another person. Bullying at its worst.): AND I also know that unless someone admits that their behavior was inappropriate, they are likely to repeat it. His new partner is not going to be immune, sadly. Wishing you your heart's desire.

anonymous Dec 12, 2014 5:07pm

Great list Edie. Very comprehensive! I think a lot of these questions can be answered somewhat indirectly through looking at a person's behaviour right?

Ie… "how do you deal with change"… it's a hard question to verbally answer, but much easier when looking at someone's life, and seeing the patterns they routinely take part in. PLus, people lie all the time.

After all, words can be really cheap, right? It's not until we can truly see the actions and patterns of the other person, that we can really understand and appreciate them for who they are.

But great list of important questions to consider!

    anonymous Dec 12, 2014 8:25pm

    Thank you. Sometimes actions speak louder than words. If we can get conversation started early on, then it might be a barometer for where the relationship can go.

anonymous Dec 6, 2014 3:07pm

I wanted to do that work Jeff Brown but my ex partner did not want to grow! Said he was too old. He was both content and afraid!

    anonymous Dec 6, 2014 6:41pm

    We can't force growth on anyone…they gotta wanna. No one is too old too grow, though. If we don't grow, we stagnate. Fear can inhibit growth. I guess that's why he's your ex-partner. Wishing a healthy, happy relationship for you.

      anonymous Dec 7, 2014 2:09am

      Yes I understand that Edie…it was frustrating and as you state I think there was some fear in there! But I had to move on as the situation/relationship was 'killing' me! xx

anonymous Dec 6, 2014 3:03pm

Thank you, Jeff. I have found that in any relationship whether it is with a partner, friend or family member, I am in ongoing inquiry. I have faced my shadow and it isn't always pretty. It takes courage to face it together.

anonymous Dec 6, 2014 2:39pm

Another question to ask is, "Are you willing to go to counseling if we get stuck?" I am amazed at how miserable couples make themselves before they reach out for help, often only when it is too late to do much damage control. Relationships are not secret things, but a communal efforts. How you relate together is how you relate to others as well.

    anonymous Dec 6, 2014 6:39pm

    Yes. Going to therapy doesn't mean the relationship is broken. Sometimes an impartial listener catches dynamics that the couple misses. I have had clients who have said in response to observations I have made: :"Hmmm, we never thought of it that way." Oh yes, often the way a person treats family members and friends is a reflection of the way he or she may treat a partner.

anonymous Dec 6, 2014 2:32pm

Edie and/or Jeff. I have been living separately from my ex-partner for 2 weeks after separating and still living together for 2 months. I feel like I did all (most?) of my grieving/healing while still in the relationship. So my question is –
I have been spending time and enjoying someone of the opposite sex's company. I am not looking to move it along too soon to being a serious/committed relationship but was wondering how do you know that it is the 'right' time to allow that to happen/want that to happen taking into account everything in this article?

    anonymous Dec 6, 2014 6:36pm

    Grief is not a one and done experience. It happens over time. Sometimes people do grieve pre-emptively as a relationship is shifting and changing. Do you have a feeling of comfort and ease with this new person? Can you be yourself fully? Are you needing to tiptoe around or put on façade? Is he someone who would fit into your life and you into his? Can you grow together and can you each be patient while that is happening? AND have fun as you explore~

      anonymous Dec 7, 2014 2:07am

      Thanks for replying Edie. I dont feel like I am putting any facades up and I am not sure what is happening or where it is headed. I just wanted some clarification/validation that I am able to let it evolve!! Cheers xxx

anonymous Dec 6, 2014 12:46pm

Great informative article. You can ask all of these questions, but the relationship will only be authentic if the partner is truthful. Ive been involved with a man for 3 years to discover he has been very deceitful and told me what I wanted to hear.

    anonymous Dec 6, 2014 6:32pm

    Thank you, Laine. You're right. People sometimes hide who they are for fear of loss. Over time we learn to hone our Spidey Sense that tells us if someone is deceiving us.

    anonymous Feb 5, 2015 3:54am

    u are right……….honesty is Nonrepresentational

anonymous Dec 6, 2014 10:14am

fantastic inquiry. i would add 'How much work are you willing to do on yourself and on relationship when the shit hits the fan? Do you believe that connections that bring up too much shadow are worth fighting for, or are you of the view that the emerging shadow is a sign that there is work for us to do together, as part of our individual and relational transformation'?

    anonymous Dec 6, 2014 6:30pm

    Thank you, Jeff. Shadow work is an important part of any relationship, since we each contain shadow and light. It is when we hide our stuff that it will emerge and bite us in the butt and take the relationship down with it. Relationships are not 50/50. They are 100/100 with each person bringing all of who they are to the table.

      anonymous Dec 19, 2014 11:45am

      "Relationships are not 50/50. They are 100/100 with each person bringing all of who they are to the table."

      That's flippn' awesome!

      PS You got a comment from Jeff Brown on this, to me that's huge!

anonymous Dec 5, 2014 7:51am

I invite you to join in a conversation here~ Feel free to add your own questions that feel essential for you.

Thank you,


    anonymous Jan 3, 2015 8:48pm

    Excellent article and questions!!
    To the person ‘Jeff’ that replied!! Great questions!!!! I agree…they should be added!!


anonymous Dec 4, 2014 7:16pm

This is a brilliant list. We explored many of these and countless other questions before we ever met in person. It created a beautiful foundation for a relationship, a relationship that continues to be filled with explorations into questions that delve ever more deeply into the core of who we are and why we’re here. Our answers, too, evolve as the questions do! ♥ Mali & Joe

    anonymous Dec 5, 2014 9:02am

    And as a result, not only are you growing your relationship, but are such glowing examples for your clients and readers. Blessings on it all~

anonymous Dec 4, 2014 7:11pm

Awesome article !

anonymous Dec 4, 2014 7:10pm

Awesome Article!

    anonymous Dec 5, 2014 9:00am

    Thank you~ Feel free to share with your friends as way of keeping the conversation flowing.

Vivek Sarma R Mar 22, 2018 7:08am

Amazing article ! Thank you for sharing your thoughts

Temahlubik Hlubikaazi Dlamini Jan 9, 2017 8:54am

Thank you so much for the article, it is thought provoking and has been helpful to me, now i know the adjustments i have to make.

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