Grieving the Loss of a Complicated Relationship
IN THIS LESSON
Dealing with Guilt and Regret
Grieving the loss of someone with whom you had a complicated relationship often brings feelings of guilt and regret. You may find yourself thinking about what you could have done differently, wishing you had said more—or less—or feeling conflicted about the past. These feelings are normal, but they can be heavy, keeping you stuck in a cycle of self-blame. Learning to navigate guilt and regret with self-compassion is an important part of healing.
If at any time these ideas and activities seem to be hurting more than they are helping, stop immediately and seek the support of a licensed counselor. These activities and lessons are designed to build healthy coping skills, but they do not replace therapeutic processing of a painful loss.
The Emotional Journey of Losing a Complicated Relationship
Understanding Guilt and Regret in Grief
Guilt and regret often come from the gap between what happened and what you wish had happened. When a relationship was strained, you may feel guilty for:
Not reconciling before they passed
Setting boundaries or cutting contact
Feeling relief after their passing
Harsh words said in the past
Not being able to “fix” them or the relationship
Regret may come from:
Missed opportunities for connection
Unspoken words or unresolved conflicts
Wishing the relationship had been different
Because you can no longer change the past, these emotions can feel particularly painful, making it easy to get trapped in “what ifs” and “if onlys.”
How to Work Through Guilt and Regret
Recognize What Was (and Wasn’t) in Your Control
Not every relationship can be healed. People are responsible for their own actions, and sometimes distance or estrangement was necessary for your well-being. Ask yourself:
Did I do the best I could with what I knew at the time?
Did I make choices that were necessary for my safety or mental health?
Was I responsible for fixing everything in the relationship?
Acknowledge the Complexity
Your relationship was not defined by a single moment. Instead of focusing on what you did or didn’t do, try to see the full picture—both the struggles and the efforts you made.Reframe the Narrative
Rather than telling yourself, “I should have done more,” try shifting your perspective:
“I made the best choices I could with the circumstances I had.”
“I wish things had been different, but I can still honor the lessons from this relationship.”
“I will use what I’ve learned to show up differently in the relationships I have now.”
Express What’s Left Unsaid
Even though they are gone, you can still process unresolved emotions:
Write a letter to them, expressing anything you need to say.
Speak aloud what you never got to tell them.
Create a ritual—light a candle, visit a meaningful place, or write their name in the sand.
Forgive Yourself
Self-forgiveness doesn’t mean excusing everything. It means recognizing that you are human, that relationships are complicated, and that healing is possible. Try writing down:
One thing you’re ready to release
A kind statement to yourself (e.g., “I am allowed to grieve and heal.”)
A reminder that you deserve peace
Shift from Regret to Meaning
Rather than staying stuck in what you wish had happened, think about how you can use this experience to grow:
Can you be more present in your relationships now?
Can you set healthier boundaries or express your feelings more openly?
Can you offer yourself the compassion you would give a friend?
A Final Thought
Guilt and regret are signs that you cared, even in a complicated relationship. But you do not need to carry them forever. Healing is not about rewriting the past—it’s about making peace with it and allowing yourself to move forward with compassion. You are allowed to find closure, even without all the answers.
Regret Release Ritual
To help you process the guilt and regret you may be experiencing after a complicated loss, try the "Regret Release Ritual" activity. Find a quiet space and write down on separate pieces of paper specific instances of guilt or regret you're holding onto – things you wish you had done differently, words left unsaid, or opportunities missed. Take your time with this, allowing yourself to fully acknowledge these feelings. Then, create a small, personal ritual to symbolize the release of these burdens. This could involve burning the papers (safely!), burying them, tearing them into tiny pieces and scattering them in the wind, or placing them in a designated "release" box. As you perform this ritual, repeat a phrase of self-compassion, such as "I did the best I could," "I forgive myself," or "I release this regret." This tangible act can help you begin to let go of the past and move towards self-forgiveness.
If, while writing down your regrets or performing the release ritual, you find yourself becoming overwhelmed by the intensity of your emotions, please stop. This activity is meant to be a tool for processing and healing, not a source of further distress. It's perfectly acceptable to put the materials away and revisit them when you feel more emotionally prepared. Perhaps try engaging in a gentler self-care practice, like listening to calming music, spending time in nature, or talking with a trusted friend or therapist. Remember, grief is a journey, and there is no right or wrong way to navigate it. Be kind to yourself, and allow yourself the time and space you need to process your emotions. If you consistently find that activities meant to explore your grief trigger intense emotional pain, it's highly recommended to seek support from a grief counselor. A professional can provide a safe and supportive space for you to explore these complex and often conflicting emotions and develop healthy coping mechanisms.
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