Nancy Ruth Deen | Breakup Coach For Anxiously Attached Women

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8 Powerful Questions to Ask Yourself After a Breakup (And Why)

Today I want to walk you through some of my favourite journal questions. These are questions that will lead to deeper insight into your own personal healing journey, and help you move through the grieving process with compassion. After all, you deserve that.

I was inspired to write this article as a lot of people reach out hoping that as a breakup coach, I can answer their questions with definite answers to their situation. I can completely understand this because I’d be lying if I said I haven’t done the exact same.

Questions like:

  • “Will we get back together?”

  • “Was my ex cheating on me?”

  • “Are all men/women like this?”

  • “Should I just move on or hold out for my ex to come back?”

In my experience, those questions stem from being uncomfortable with uncertainty, but they don’t actually lead to healing. At best, they lead to temporary relief in the moment.

What I’ve learned as a coach, and having gone through my own series of confusing breakups, is that the better the question—the deeper the insight and healing.

So today, let’s put away our need for yes-or-no questions and let’s get reflective.

Feel free to grab your journal and write these down to do tonight. And comment below which question led to the most insight for you.


  1. “What “pattern” do I see in my last relationship? Where has this pattern shown up in other relationships and parts of my life?

    • Do you find most of your exes unfaithful?

    • Do you find they’re always the one leaving you first?

    • Do you find you date people who take your generosity for granted?

    • Do you find your exes treat you like dirt?

    Get to know what pattern is showing up for you so you can start gaining awareness. In my experience, this is the FIRST step towards healing and taking control during your breakup. When we can pinpoint the pattern, we can begin to release it.

  2. “What have I been struggling to let go of when it comes to my ex/last relationship?” Believe it or not, many people I speak with think their ex has to do X or Y in order for them to let go of how they feel. (Sound familiar?) This isn’t the case. You don’t need them to apologize, change, or do something for you to be a peace with yourself.

    By identifying and CHOOSING (yes, making the choice!) what you want to let go of, you put the power back in your hands and can make this decision without them needing to do anything. This question will actually help you become aware of what you do in fact want to release, instead of focusing on where they’re not doing their part in the breakup.

  3. “Where have I been neglecting my own self-compassion?”

    Most of my clients are way too hard on themselves, and I can certainly relate to this. We live in a world where we are constantly being asked to “fix” ourselves as if we were born broken. It’s horrifying. As a result, we are not gentle on ourselves during an extremely emotional time. Worse yet, most of us don’t have proper role models to teach us about how to deal with our emotions and breakups (hence why I started coaching people through their breakups!)

    Have you been:

    • judging yourself for how long it’s taking to get over your ex?

    • blaming yourself for everything that went wrong in the relationship?

    • replaying a conversation you wish you could take back?

    • angry that your life isn’t where you thought it would be by now?

    • beating yourself up emotionally for how “horrible” you were towards the end of the relationship?

    Be kind to yourself. Talk to yourself the way a loving parent would talk to their child going through hardship. You don’t need “tough love” right now—you need self-love.

    Pro tip: Write down up to 10 ways you notice yourself punishing yourself, or going down a self-deprecating rabbit hole mentally. Write these all down on individual sticky notes, and then tear them up and throw them in the trash. It’ll feel so good to decide to let go of them in this way.

  4. “Where can I take responsibility for what happened in my relationship?” Taking responsibility is not the same as blaming yourself or accepting full responsibility for the downfall in the relationship. It’s about accepting your side of things, without judgment. I know how tough and triggering it can be to answer this question.

    When I was going through my last relationship, I always believed my ex was trying to tell me that I was less than him. I could see this everywhere: my career, education, and lifestyle just wasn’t up to par with his standards. During my breakup, I realized that he wasn’t the first person to plant this idea in my head; I had a whole history of feeling this way, and he just happened to be the person who revealed my own thinking to me. Years later, I’m engaged, and I see that old story (remember question #1) differently. I see this words and actions as genuine support, and I feel grateful that I chose to take responsibility for how I saw things so that I could course correct to find someone who saw my value. I invite you to consider this question every day if you need to. Don’t stress if today isn’t the day to answer it. Give yourself kudos for continuing to read through these questions and planting the seed.

  5. “Who do I want to be in my next relationship?” Many times, we don’t consciously think about who we want to be; we just observe how our partner or exes were and where you stood in that. Today, I invite you to expand your mind to think about who you want to be, because that’s how you’ll naturally attract a great match. It was only in 2017 that I started to decide how I wanted to show up in my relationships, which ultimately led me to finding my match in early 2018. Yes, you can shift your mind without changing who you are. This is all about becoming aware of the life you want to live, and what you’re no longer willing to settle for. And, when you compare who you want to be with what you were “handed” in your last relationship, your ex doesn’t seem all that desirable.

  6. “Do I struggle to receive love?” Chances are, you’re a giving, loving, generous partner—but you've managed to attract someone who takes more than they give.

    I find that the majority of my clients don’t realize that underneath their unbalanced give-and-take relationship is a feeling of unworthiness. Unworthy of love.

    I used to do so much for my ex—so much it’s almost embarrassing. I’d clean his apartment, make food even though I didn’t like to cook that much (and he NEVER cooked), and I’d just settle for anything he wanted to do because deep down, I thought if I wasn’t always giving, then I wasn’t worth staying with. This happened at such an unconscious level, but this was a belief I held.

    This was a painful realization for me, but one of the most powerful ones that changed my life almost immediately. As a result of this unconscious belief, I attracted men into my life who rarely bought me gifts or showed me their love, and I felt like I was always adjusting to what they wanted. I didn’t know myself in the relationship. I was scared of being myself. Stepping into your authenticity means knowing you are deserving of love, and that you don’t need to work hard to gain love from a partner. I talk more about this in the next question.

    I work with my clients on identifying and letting go of these beliefs so if you want to know more and do a private session based on your unique relationship, inquire about booking a session with me here.

    Do you struggle to receive love? Write down what comes up for you when I say that.

  7. “I’m deserving and worthy of love because…”: I love this question because your unconscious default narrative might be that you DON’T believe you deserve love, so with this question I want you to write 20 (YES! That many) reasons why you DO deserve love. I promise you that your list should be about 100 reasons, but because we are just getting our feet wet with this question, let’s start with 20. Feel free to keep going, and recite this to yourself daily in the mirror. Stick it to your wall and relish in all the good feels.

  8. “The healthy things I’m doing to support myself during my breakup are”: With this question I want you to acknowledge what you’re doing that’s leading you towards healing. This not only helps you actually consciously uncover what’s working for you personally, but it helps you see more of what you want to keep doing.

    Sometimes it’s easy to get caught up in the “I’m f***king up so much during my breakup and texting my ex even though I know they’re bad for me!” that you forget that while you’re doing that, you’re also doing a lot of loving and healthy things, like reading this article literally showing you how introspective, thoughtful, and dedicated you are to your own healing.

    This question is meant to give credit where credit is deserved—and you, my friend, deserve a ton of it.

I hope you’ll take some time tonight to answer each of these questions. Set the mood by lighting candles, grabbing a journal, and doing some deep breathing before. Let the monkey mind relax while you go deeper with yourself.

Feel like you need your whole breakup situation analyzed? Order an in-depth breakup analysis HERE.

Hey there, I’m Nancy! I’m a Conscious Breakup Coach dedicated to giving you conscious breakup advice during, well—one of the hardest times of your life. Let me know if this blog resonated for you by leaving a comment!

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