There’s nothing like the first. The first family. The first friend. The first kiss. The first job. The first baby. The first heartbreak.

The first time or experience or relationship lays the groove of a blueprint for how we navigate later, similar experiences. Our first experience of a family that occurs in our family of origin creates a groove in psyche called “family”, much like the groove in a vinyl album. When the needle of a later experience sets down on the groove of “family”, you will automatically think about your family of origin, and the overarching feeling of what it was like to be in your family will color your expectations of current or future family. Likewise, our first experience of marriage is often our parents’ marriage; what we learned, saw, and absorbed there affects our expectations, hopes, and fears around our own marriage possibly more than any other factor.

And so it is with first love, which, quite often, is also first heartbreak. Our first experience of love affects our future expectations of love, which, as you can imagine, affects how much anxiety is activated around a real, present, available partner. For if our first heartbreak was not only wrought with pain but also with shame, we can understand that this underlying belief of “not enough” would weave its way into later relationships. Herein we find one of the root causes of relationship anxiety.

When I ask a coaching client about early pain, they usually don’t talk immediately about first heartbreak. But when I press further and specifically ask about it, the painful story will come spilling out. And on the heels of the pain is the story about themselves regarding the break up, which almost always includes some rendition of the running subtext song called, “What’s wrong with me?”

My first heartbreak occurred in 7th grade. Up until that point I only had had positive experiences with boys, most of whom were my good friends. I felt liked, loved, and, in some innocent way, wanted. All of that changed when I attended a new school in 7th grade. I suddenly felt like the odd one out. I didn’t feel attractive anymore, and I felt inadequate compared to the popular girls who always seemed to know exactly what to wear, say, and how to act. Towards the end of the year, when I learned that a cute boy liked me, I decided I liked him, too. We spent a week talking every day at school and talking every night on the phone. For five days, from Monday through Friday, I was in heaven. But on the sixth day, as quickly as it had started, it ended. My friend and I were supposed to go to his house to swim, but that morning the friend of my “boyfriend” (if you can call it that) called me to tell me that he didn’t want to see me anymore. I was blindsided. Just the night before we had talked late into the night, all sweetness and ease. I didn’t understand. And I was heartbroken.

Looking back, I can see that mostly what I felt was shame. Since I wasn’t given a reason (I’m sure he didn’t even know himself), I was left to assume the worst: I must have done something wrong. Maybe I wasn’t pretty enough. Maybe I wasn’t funny enough. At the time, all I knew was that something that had felt good and affirming was taken away from me, and I was left to navigate the shattered aftermath alone.

One of my most vivid memories of the days following this heartbreak was sitting on a barstool at my grandmother’s house, talking to her across the counter while she was cooking. My grandmother loved me unconditionally, but she had no idea how to be with big feelings, and when I shared that I was feeling sad about the break up she said something dismissive like, “Oh, honey, there will be plenty of other boys. You’re too young to be this sad about one boy.” Well, that obviously wasn’t helpful. Number one, she was telling me that I shouldn’t be feeling as deeply as I was feeling. And number two, she was telling me not think about and instead focus on other boys. Since I didn’t have anyone to help me through the grief, it did what unattended grief does: it morphed into self-doubt and anxiety.

I don’t remember consciously thinking, “I’m not worthy”, but I know that’s what I felt. This feeling of inadequacy and unworthiness was compounded exponentially the next weekend when I wasn’t invited to a classmate’s birthday party and I heard later that my best friend was roller-skating with “the boy” the entire time. He apparently liked her now! Again, I don’t remember the exact stories I told myself in that moment, but I remember feeling absolutely worthless: left out, unloved, unwanted, and small.

This is how the stories we tell about ourselves are created.

It’s not necessarily the pain of the first heartbreak that leaves the scars; it’s the stories we tell ourselves that etch the grooves of self-doubt and low self-worth, which we then project onto our partners as a protective mechanism in the form of “you’re not enough” (not social, good-looking, witty, educated, etc enough) or onto ourselves through intrusive thoughts (“What if I’m gay?” “What if I hurt a child?” “What if I’m incapable of love?”). If we convince ourselves that we or our partners are sufficiently lacking in some vital way, we can walk away from the risk of love, which includes the risk of heartbreak. It’s all about protecting these unspeakably tender hearts that not only believe that they can’t handle pain because we were never taught how to handle it but also believe that we’re not worthy of love and that when our partners see our true selves they will leave.

If you had had someone in your early life to sit with you while you cried – about heartbreak or anything else – you wouldn’t fear your pain now. If you had had someone who could have guided you with wisdom through the pain of heartbreak, encouraging you to feel it fully while also helping you skirt away from telling yourself a story about your self-worth, you would love yourself more and you wouldn’t fear love quite so much. When I think about guiding my sons through the inevitable emotional landmines of early love and the heartbreak they’re likely to experience, I  imagine saying something like, “It’s so painful when a relationship ends not by your choice or when someone doesn’t return your affections. When this happens, it’s easy to tell ourselves a story about why the person left, but the truth is that we really don’t know. Some people aren’t ready for real love. Sometimes it’s too early or the big feelings are too scary. For whatever reason, this relationship was not meant to be at this time. Tell me what it feels like inside. Tell me what stories you might want to tell yourself about yourself. Let me be with you through the pain”

The more we can feel the raw pain directly, the less we need to go into our heads to try to make sense of it. Sometimes there’s no making sense; there’s only loving ourselves through the pain of life, which sometimes means the pain of loss.

What are your stories of heartbreak? What can you imagine saying to the young you who told a story that the first breakup was because you were unworthy in some way? Do you see the connection between early heartbreak and relationship anxiety? When we can attend to the old pain and address the stories with wisdom, we heal at the root. And the more we do this deep healing work, the more we can open ourselves to love in all forms, with all beings, in all ways.



  1. My first two relationships were both long distance. Even though I broke up with him, at the time I believed that he didn’t want to be with me anymore because I was far away and I wasn’t the idea he had of me. This led me to believe that I wasn’t enough and that someone would only love me if I was with them. My second boyfriend broke up with me because the distance was too painful. Again this confirmed my belief that I would only be loved if I was always there.
    I hope I can figure out what I’d tell my young self, except for the fact that things are going to be okay.

  2. My greatest heartbreak came from friends. When I was in my early twenties and at my first job, a woman I worked with befriended me. She and her husband cared for me and referred to themselves as my second parents. After six years of friendship, she all of a sudden cut me out of their lives without any explanation. I apologized through letters and tried to make sense of why she would completely shut me out when all seemed well days before. Nothing in return. This lack of closure led my mind down all sorts of self deprecating holes. For years after that, and even now, I shy away from getting this close to people, especially when they want to be part of my inner most circle. After losing these friends, I wonder if it hurt even more than ending a romantic relationship? I am still mourning in many ways almost 15 years later.

    • I know exactly what you mean. I had a very similar experience as Kathleen’s. With a childhood friend – we were like family for 8 years. And for reasons best known to her, she decided to distance herself and cut me out. She made this decision on her own without any explanation. This really shook me and left me feeling very confused, sad and in constant states of self doubt for years. I struggled with trust and intimacy cause a friendship that was so central to my childhood had fallen apart so. But there was an upside to this- this intense experience opened many doors for me (I realize this now in retrospect)- I began to take my questions inward and the answers came as i stumbled upon new books, websites and teachers. There was a beautiful phase of spiritual curiosity and discovery and gradually I began to make space for healthier friendships. I also wrote to this friend recently sharing my side of the experience and in an attempt to make peace with it once and for all. This was a great relief. Her response was disappointing though- she was not ready to acknowledge or receive this respectfully, despite all these years. But this didnt matter anymore, I was still relieved knowing I had done my part and I dont feel the heaviness of the experience. Hoping you find these insights helpful. Wishing you all the love and support through your experience.

  3. This subject is always kind of funny for me, because my boyfriend is my first real love, before him I only had “platonic” relationships. I would secretly like a guy for ages, and I’d imagine myself being with him, having a relationship and whatsoever, but I’d never EVER say a word to him about my feelings. This situation became a habit in my adolescense, and you could imagine how my OCD is grabbing onto this memories with all the “what if X liked you and you never knew?”, “what if he was the one?” and all that.

    When I was 21, I met this guy and I became really obsessive about it. One day I told him about my feelings, he didn’t like me as I did, so I felt really bad, like something was wrong with me, and I started asking myself what I did or said wrong, everything you say in the post. I think that was a heartbreak, even though we weren’t anything, it wasn’t about the guy or the fact that he didn’t like me, but the stories I told myself.

    Then, at age 22, I met my boyfriend and I completely understood why my previous stories didn’t work out, but the scars were there, and once I started feeling really confident with my relationship and in a safe place, anxiety started to show its face again.

    So, yeah. I’ve always linked my previous frustrated crushes with the anxiety that my real relationship causes me. And this post makes it clearer 🙂

  4. Sheryl, you’re such a great mama. Your boys are lucky to have you. I know that no mama is perfect but you’re a really good example of conscious parenting. My daughter is only two, and at two she deals with some big feelings that she can’t really explain yet. I’m trying to be there with her and help her through those big feelings (tantrums) the best I can. Part of this is trying to help her know what her feelings are. The other day she was having trouble getting a puzzle piece in and her temper was starting to flare and she came over to me and said “I’m getting a little sustrated” (her word for frustrated). Blew me away. Little ones can take in so much more than we think. I digress a bit from the first heartbreak, but I also think about parenting her through those future challenges such as heartbreak, starting now with her two-year-old challenges.

  5. This topic is so raw for me. My first heartbreak was the single hardest thing I’ve ever gone through. I was so infatuated, buzzing with love for a year of my first love. Pure, devotional “love”, and when he simply ended it through a text message, for no reason other than didn’t feel it anymore, I became shattered for truly, years. I was 17. In university we would meet up occasionally and the wound would re-open. I always believed if I did the right combination of things, just molded myself the right way, he would have am epiphany of his mistake. I ruminated and longed and wrote poems and obsessed for nearly 4 and a half years. Anyone and anything to do with him surged so many painful stings. I always thought, if someone asked me to travel across the world by foot if it meant I could be with him, I would. I would have done anything. I meant that.
    Through those years I went on first dates, some second dates, one unavailable man for a few months. But nothing beyond that. My standards became unbearably high and I would cut people off for things such as “too soft hands,” “weird interest”, just anything that made them not quite right. I didn’t see this as anything other than me being a super independent, “Not settling for anything!” Young girl. I see that now as a result of this heartbreak.

    Now, I am on this website because one of those men surprised me and fit the exact bill: same core values, desire for a family + commitment, same ethical viewpoints, humour, career path even. I knew I couldn’t let this one slip by. Now 8 months into the relationship, I have been at times consumed with the guilt and shame of having relationship anxiety and obsessed over his flaws and shortcomings when this is all I thought the heartbroken 17 year old wanted.

    I totally associated as you say, “love with longing” and the feeling of not getting what I so badly wanted. Now that there is this amazing man saying hello! I love you! Let’s do everything together, You’re safe here!” I am so so mad at myself that I can’t just relax and reciprocate to the same intensity I once had. Thank you for writing this, I wondered if that painstakingly long grief had anything to do with it.

    I felt like I had so much love left to give, with nowhere to put it, and it morphed and twisted into such a deep pain in my heart, one that I made a habit of finding some sick comfort in, as evidence that no other little loss or failed relationship would ever, ever be felt as deeply as that one did. Whew. It’s hard.

    • Yes, this is exactly what I’m talking about. Please know that as long as you’re angry at yourself for having relationship anxiety it won’t move through you. The biggest piece of this work is learning to remove the projections – both on yourself and your partner – so that you can tend to the raw and core pain that need your attention.

    • I feel this on such a deep level. My relationship of 6 years just ended. I am in the stage where I feel like I would do anything to be together again. But I know we are on separate pages in life, and for whatever reason, it’s not meant to be right now. I am absolutely shattered, and trying to figure out what to tell myself, and stop letting the “stories” about myself run the show. It’s so hard to sit with the uncertainty of the future right now, especially when for years that’s all I imagined my future being. I’m not sure what the next steps are, but I hope I find someone who can love me and be there for me in that same way.

  6. May I be, more like you, to my hurting self.

  7. Oh, my Goodness.. how I’m experiencing this relationship anxiety right now as those early scars created another life event to bring another healing opportunity.. Oh soooo painful again..

    Interestingly I was taken to my memories with my parents..

    Both confessed recently that they were thinking “It’s not worth investing too much time and emotional energy into me or to fix their marriage as I will grow up soon and leave anyway.. ” .. so instead they chose divorce and chasing after other partners.. neglecting me and my sister..

    Talking about feeling not worthy.. I felt totally worthless and unwanted , especially when the partners were around.. left out in the cold.. excluded.. like an unwanted gift put on the shelf.. waiting to be de-cluttered..

    I’ve been feeling exactly the same with my husband.. for 34 years.. despite of doing a tremendous amount of inner work in the last more than 2 decades..

    Now it is so clear, though.. must have been the deepest, most protected vulnerability and grief..

    So grateful the healing that is already taking place, the shifts that I feel and sense around how I am being with me in this..

    Like a baby, I need my inner Mama to affirm that the painful situation has nothing to do with my worthiness or deserving.. that I will never leave me nor forsake me.. that I AM HERE.. holding myself as the tears are flowing.. Bowing inner Namastes.. honouring the birthing of my True Nature self.. Alive, good-willed, powerful Queen.. full of grace and dignity..

    Thank you for this article.. so, so timely. <3

  8. Hello Sheryl,

    Thanks for this great post. I don’t think that it’s always true that if you have someone to acknowledge and help you through your pain in a constructive way you won’t suffer the relationship anxiety aftermath of one (or several) early break ups. I can remember my mother doing everything (or as close to everything as possible) right to shepard me through early heartbreak. I still have RA. My guess is that I am so sensitive that even with her support I felt those losses so profoundly that the effects were severe. I also don’t remember feeling that anything was wrong with me, I knew (probably thanks to my mother) that some people just aren’t meant for others at any given time. I am now realizing what a gift she gave me.

  9. When I was in 9th grade, I dated a boy for the whole school year. Total over-the-moon infatuation, loving feelings, no hardship, the typical teenage romance. And then one day, he also out-of-the-blue ended it, over AOL instant messenger (ha!). I was completely blindsided as well. 9 months of pure bliss and happiness and over the top romance just gone. Of course I was completely heartbroken. However, I feel like what happened next sealed the deal. The same day that my boyfriend broke up with me, my best guy friend broke up with his girlfriend of 2 years. A few days later, he calls me and says that he dumped her because he wanted a chance to be with me instead. How amazing I was, how loveable I was, etc. All of the things that my sad and rejected heart wanted to hear. Unfortunately instead of turning him down and letting myself grieve, I went head over heels into another relationship. It was wonderful, it was healing )or so I thought, it was just distracting me or replacing the heartbreak I had for my first boyfriend)…. but I thought was perfect. That was, until I found out 5 months later that he was cheating on me with his ex-girlfriend. So, overall, my first breakup and second relationship were a pretty terrible framework to start my dating life with.

    Long story short, I never let myself learn to grieve. Instead, I learned that when you are feeling heartbroken and rejection, there is an easy fix: just start a new, exciting relationship to heal yourself. And this continued for many years. Ultimately it has wrecked havoc in my mind now that I’m in a relationship that I want to stay in. All of a sudden the loving feelings faded, that exciting glow and infatuation was gone…. and the urge to run to something new was so strong. It’s been a work in progress but I am making progress. Thank you as always Sheryl for your wisdom!

  10. All of your posts are relevant to me, but this one speaks to me perhaps the most. Thank you for talking about an issue that I have never ever read about before, but is so healing and needed for me and so many others.

  11. Does it include heartbreak due to breakup with your best friend in college? Before my first relationship with my current boyfriend, the girl who was my best friend, broke up with me…I mean, the friendship faded.. with her speaking less to me…she called me clingy and look for other people as friends….Now I’m having relationship anxiety and wonder if this is the reason…

  12. My first heartbreak was in high school. I was in love with a boy who was my first male friend. I was so tortured over it and we never dated or were together, but I remember being quite obsessed with him. He was outgoing and playful and very very gay. He could have never loved me in a romantic way, but was ashamed of his sexuality and that came out in ways of “leading me on” because he knew that I had feelings for him. I remember feeling so unworthy and inadequate, feelings that feel familiar to me in breakups since. I’ve never thought of that experience as being one that could color how I experience other rejections, but I do see how making it about a perceived personality flaw or defect on my part gives me some sense of power and a way to make sense of the loss and pain. If I feel that it is because of some personal defect of mine, I can maybe change the situation and not feel the pain. Now, looking back, it’s so obvious that he could never love me in that way and the ways he lead me on aren’t because of my weakness that caused him to do that, but because of his own insecurity and pain.


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