7 Reasons Why You Might Have a Hard Time Letting Go of a Past Relationship

a therapy benefit you may not realize you have


Many of us are hard on ourselves when we think we’re struggling to let go. And that becomes more complicated because we often judge ourselves and our process.

As such, I’ve written this to help you to:

  • discern between struggling to let go and functionally reflecting

  • offer some insights as to why this struggle may happen

  • underscore the advantages deep reflection can actually have on your overall process

  • empower you to recognize that our minds work in purposeful ways that we can figure out

The healthier and more productive your reflection process is - the more genuine compassion you can develop for yourself. 

You may even notice experiencing a greater sense of empathy for the relationship and person you are in disconnection with.

Reflection paves the way for unique insight about the nuance of your feelings. 

You can build heightened awareness around your and your ex’s behavior. 

And you may likely achieve a better understanding of how and why the relationship started and ended the way it did. 

When successful, reflection can lead you to the peace of genuinely accepting life as it is today.  

This process is important. 
It’s necessary. 
It’s healthy. 
And above all, it’s completely normal.

Psychologically speaking, we need to do this in order to successfully grow forth.
To move forward in a healthy and functional way.
To be wiser about decisions we’ll face in the future. 

But challenges moving on can be as real and as timeless as love itself. And if we are judging ourselves about “not letting go,” we may be making ourselves feel more stuck than we need to.

Here’s 7 reasons why it might feel hard for you to let go:

1.  Even if it was traumatic, the past can actually feel safer than the present.

A story from our past can feel safer than the present because the old story is more familiar

For many of us, familiarity feels safe - even if it is uncomfortable.

And as uncomfortable as it might be, we tend to feel safer because we are “in the know.” 

The dilemma is the amount of mental and emotional energy to stay in the past - does not serve us today. It serves us about a time that is no longer.  

The present is a time that is new to us. 
The present offers much less information about what’s going to happen next.
And unpredictability can make us feel much less safe, much more scared, and much more inclined to go back to the story we already know.   

2.  The past holds memories of a time you believe you were happier.

Was it the relationship?
Was it the time in your life?
Was it both?
Other things?

If there’s a neurocognitive connection to a past relationship that you believe represents a time you thought you were happier - it’s important to look closely at the details.

Is it possible that you’re holding onto the nostalgia of those feelings? The time period? The person?

We need to be careful with how rosy our glasses become for the past. For many of us, parts of the past can be easy to romanticize. Especially when we are faced with new and neverending challenges in our immediate present.

Are you open to the possibility that you can feel that happiness again?

Do you believe happiness changes form all the time and it may require some reconsideration on our end? 

As we grow, so should the things that make us happy. As we heal, our understanding of ourselves and others should broaden and deepen. Our own internal unhappinesses should become more apparent. Recognizing that some parts of happiness are an inside job - is huge. 

3.  You are unresolved about the facts related to the past relationship and/or your perspective does not line up with your ex’s.

Breaking up is hard to do. 

But when you and your ex disagree about what the “reality” was - it’s even harder.

In some cases, it may be natural to want to defend your ideas; to attempt to get the other person to see things the way you do.  

When someone important to us doesn’t share our perspective, we tend to feel invalidated, unseen, and unimportant. In extreme cases - even gaslit.

It’s hard for many of us to reconcile that peace and love can exist in a space of disagreement - but it can. And if we aren’t open to finding that space, it can make it feel like we are stuck; on them or on the relationship.

Multiple perspectives being true at the same time (barring any form of lying and abuse) - is truly one of the greatest skills you can acquire for managing human relationships.

4.  The relationship might not have been as healthy as you think it was.

Warning: this can be super difficult to face directly. 

I remember an early career talk with one of my mentors. She shared about a client that had recently lost his wife and was feeling ready to date, but was concerned others would think it was “too soon.”  

I’ll never forget her perspective—the healthier the relationship, the easier it can sometimes be to move on.  

I believe this to sometimes be true. 

When a relationship is founded upon and/or comes to exist with genuine love, trust, and safety, - it makes sense that there’d be less hangup over dysfunctional communication when it ends.

There’s no doubt, no mistrust, no confusion; it just completes itself. Grief can happen in a much less complicated way.

But when a relationship is devoid of some (or all) of those things, it’s much easier to feel preoccupied. 

It becomes harder to genuinely move forward. 

There’s confusion, hurt, pain, and often deep attachment wounding.
(both triggered from childhood and from the relationship itself)

5.  You have a family history that includes people who also have a hard time letting go.

We learn how to cope. We learn from those we watch cope with difficult things.

It’s not uncommon for people who have a hard time letting go - to come from broken homes, unhappily divorced families, or even intact families that struggle to deal with conflict in effective ways. 

We learn how to deal with thoughts and feelings from the people we grew up with. From caregivers. From those we spend time with.

Without realizing it, you may have inherited a pattern of being unable to work your way through a past relationship. 

Or, you may have never learned how. It might never have come up. 

Perhaps it wasn’t modeled for you.

Maybe you observed your family harboring long-term feelings of resentment, bitterness, and/or a refusal to forgive and move forward.

It might help to consider if you may be responding automatically in predisposed ways that are surprisingly similar to even older stories from your past.

6.  You don’t know how to deal with something that is happening in your life today.

Spending a lot of time thinking about something from the past can be a great distraction from the challenges of today.  

This process is usually unconscious, meaning - we aren’t aware of it. 

Here’s an example:
You are in a new relationship and you are re-experiencing a similar type of struggle that you experienced in the old relationship.  This can cause a PTSD-like effect, whereby old thoughts and feelings become triggered. You’re now focused on how this experience impacted you in the past and are looking away from where and how it stands before you today.

Second example:
A current relationship presents new challenges and limitations that you feel scared of, unprepared to deal with, or hopeless about because you don’t recognize them as familiar. 

Third example:
You’re single and are feeling unsuccessful about “finding someone new” to be in a relationship with.  When this happens, you put the rosy past glasses on and choose to believe that no one will compare to the person you used to be with.  This distracts you from the opportunity to give and receive from future people and relationships. 

7.  Plain and simple—it can be very hard to say goodbye.

Love is love.  

But sometimes, it’s just not the right fit, time, or place. 

Or, it was – but it is no longer.

Love, connection, intimacy and sex are some of the most powerful constructs we know. 

But these elements don’t always mean that the relationship has the potential or the level of functionality that we need to sustain health and balance in our lives. 

Saying goodbye to a relationship, another person, unlived dreams for the future, and parts of ourselves is painful.  It’s a kind of death. 

If you’re having trouble letting go, ask yourself if you have truly taken the proper time to grieve, to cry, to brood, and to be just plain sad.  

Are you being compassionate?

Are you allowing it to be a process that can take as long as it needs to?

Are you able to explore safely on your own? With others?

Individual therapy can be an incredible opportunity for someone struggling with feeling like they just can't let go of something. Whether it’s a person, a time period, or any other part of their life they feel they’ve lost - therapy can help to make sense of it. Stuckness is not a permanent state. But to become unstuck, does require that we are able to recognize our thoughts and feelings on the matter. How our behaviors connect to it. And open ourselves up to exploring it from new angles. New angles offer new thoughts and feelings. And new thoughts and feelings lead to new, more empowered behavior choices.

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