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There are few experiences more powerful than the sense of “what might have been”. It’s the lingering sense that something truly meaningful, truly life changing slipped through our fingers to be lost forever. A connection that never grew, a potential relationship that never had the chance to become real. It’s not the sharp pain of heartbreak associated with breakups, but a slow, lingering wondering of what could have been if fear hadn’t got in the way. 

So many people will resonate with that feeling and know it all too well. Two people meet and there is something undeniable between them, chemistry, ease, compatibility and a mutual recognition that this could be something special if worked through. There is a magnetic pull that feels exciting and unsettling at the same time. Yet, despite this, one or both hold back. They retreat into safety, convincing themselves that it is “not the right time” or that “caution is better” or “it wouldn’t work anyway”. 

However, on a deeper level, it isn’t about timing, circumstance or location, it’s about fear and fear alone. Fear of rejection, fear of loss, fear of being seen and known, fear of opening up and being vulnerable and fear of history repeating itself. It’s the fear that past experiences will come back to haunt us and we should steer clear. 

Fear sabotages and it goes about it’s business in a quiet way. It doesn’t scream in our ears, it whispers quiet logic at us. It tells us to wait, to think about it, to be “realistic”. It parades itself as “wisdom”, but more often, it is self-protection. Our mind will start to build stories to consolidate this narrative and promote distance. “ they can’t be really feeling the same”, “It’s not practical due to (this or that), “ there is an age difference or they live too far away”, “ it’s not the right time”. Woven amongst these stories is usually an older pain coming up. A fear of abandonment, rejection or betrayal. This shapes what we all tell ourselves to avoid risk. 

In therapy, I see many people who struggle with relationships that have ended. Yet, I see an equal amount who have issues with the ones that never began. These ghostly “almost” relationships, still float around in our memories, mostly because there was never any closure, because there was no beginning. When something never really starts, there is no end to process, even though it feels that way. Yet, our minds will keep returning to them, filling in the gaps with imagination and fantasy. Do they still think of me? I wonder if they are replaying moments like I am? Above all, you shame yourself for letting them go.

There is a concept in psychology called the “counterfactual narrative”. A mental version of things we build up in our psyche of events that didn’t happen but could have. Our brains are wired to create stories like this because our brains dislike uncertainty and strive for resolution. Yet, the very thing that we are fixated on traps us in a thinking loop. We idealise events, comparing others to this imagined version we built up, a though of what could have been. The trouble is that fantasy often beats reality hands down.

Chemistry between two people is easy to attain. It’s exciting, addictive and instant and often attached to the “honeymoon period”. However, chemistry alone doesn’t create connection, courage and curiosity do. Love always includes risk. Exclude the risk and you exclude the love. It means stepping into the unknown with bravery and being curious about the path ahead. This also means rejection and disappointment are possible outcomes. Waiting until we feel “safe” or “ready” is another way of saying we are not willing to tolerate uncertainty. Emotional safety doesn’t come from avoidance, it comes ultimately through vulnerability. 

When we fixate on the one that got away, we are not usually longing for the person but the version of us that we might have become with them, more open, more trusting and more importantly, more alive. The fantasy represents hope. The possibility that being able to love would have been easier and that connection could have healed us. The painful truth is that this fantasy existed only in the mind. It was never truly tested by adversity, conflict or the daily grind of living together. That is why “what might have been” feels perfect. It never had the chance to be imperfect. A place where working through can build in a relationship. 

Over time, this experience may turn into regret. We tell ourselves what we could have done differently or berate ourselves for doing nothing. However, we can also learn from this regret. It can shine a light on the fear and show us where we stopped ourselves from showing up fully, where we chose comfort over courage. Instead of punishing ourselves, regret can give us all the information we need to do things differently next time.

Self-reflection might ask, “What was I protecting myself from?” and “What would I have risked by showing up more honestly?” “What does this tell me about my relationship with fear, intimacy and vulnerability?” The answers to these questions point us towards the inner work that needs to be done. Not necessarily to win back the person but to free ourselves from the patterns that created the hesitation.

Love in its truest sense doesn’t wait for us to feel unafraid. It wants us to act in spite of the fear and to risk disappointment and rejection in exchange for possibility. Meaningful relationships are not usually created by people who seek safety all the time. They are made by the people willing to feel uncomfortable, to tolerate uncertainty and to let themselves be vulnerable and seen, even if it feels dangerous to do so. 

When fear wins, we stay safe, but we stay alone or in the status quo. We protect ourselves from heartache but also from connection, even if that connection is staring us in the face. Later this need for safety shows up in “what might have been”. Healing begins when we stop running from the truth. When we can look back and say, “I was afraid, and I chose safety, that’s what I knew then.” Acceptance of this won’t erase the regret but softens it and allows us to grieve not only the loss of a special person but indeed, the version of us that couldn’t take that risk.

The ache of what might have been may never disappear entirely, but it can become something else, a reminder that love asks for risk, that vulnerability is strength, and that the greatest loss is not rejection but the chance we never took. Who knows, life is such that we may even get a second chance to do the right thing, if only we can allow ourselves.