The Psychology of Regret: Why We Can’t Let Go of the Past

Regret is one of those emotions that almost everyone carries like an invisible backpack. It shows up in small ways—like wishing you had spoken up in a meeting—or in heavier forms, such as replaying a failed relationship or career choice over and over in your mind. Psychologists call regret a counterfactual emotion because it grows from imagining “what could have been” if only we had chosen differently. And while regret can be painful, understanding how it works in the human brain can help us learn how to move forward instead of getting trapped in endless “what ifs.”

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Why Regret Hits So Hard

At its core, regret is tied to one of the brain’s most powerful functions: memory. The prefrontal cortex, the part of the brain that handles decision-making and reflection, plays a central role. When something doesn’t turn out the way we hoped, this part of the brain replays the event, searching for mistakes. This process is called counterfactual thinking—mentally constructing alternate versions of reality.

The trouble is, the brain often treats those imagined alternatives as if they were almost as real as what actually happened. That’s why regret can feel so sharp. We don’t just remember what happened—we vividly picture the better outcome we missed, and the emotional pain that follows can be intense.

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The Stories We Tell Ourselves

To make this idea more relatable, let’s look at a few everyday situations.

Career crossroads:

Sarah turned down a job offer in her twenties because she thought it wasn’t “prestigious” enough. Years later, stuck in a stressful corporate role, she sometimes lies awake at night thinking, What if I had taken that job? Would I be happier now?

Relationships:

David broke off a relationship because he felt he wasn’t ready for commitment. A decade later, after watching his former partner build a family, he finds himself scrolling through her social media with a deep ache of regret.

Everyday moments:

Even simple choices can leave us with regret. Missing a friend’s wedding because of work obligations, or not saying “I love you” before it was too late, can replay endlessly in the mind.

In each of these cases, what hurts isn’t just the memory of the event—it’s the imagined life in which the person had made a different choice.

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Why We Can’t Let Go

So why is it so hard to let go of the past, even when we know nothing can change it? Psychologists suggest three main reasons:

1. Regret reinforces learning.

From an evolutionary perspective, regret is useful. It teaches us to avoid repeating mistakes. If touching a hot stove burned you once, regret helps you remember not to touch it again. But when applied to complex life choices, this “learning loop” can become overactive, trapping us in rumination.

2. We believe in personal control.

Humans have a strong need to feel that we control our destiny. That’s why regrets often focus on things we could have controlled—what we said, what we did, what we chose. When we feel we “should have known better,” the regret deepens.

3. Our culture glorifies perfection.

Modern society often pressures us to make the “right” choices in careers, relationships, and lifestyles. Social media intensifies this, offering constant reminders of paths we didn’t take. Comparing ourselves to others fuels regret like gasoline on fire.

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Moving Forward: Turning Regret Into Growth

The good news is, regret doesn’t have to be a prison. With the right mindset, it can be transformed into a guide. Here are a few approaches that psychologists and therapists recommend:

Practice self-compassion.

Instead of harshly criticizing yourself, recognize that regret is a universal emotion. Everyone makes choices with limited information. You did the best you could with what you knew at the time.

Reframe the story.

Ask yourself: what did I learn from this? How has this regret shaped who I am today? Turning the focus from loss to growth helps soften the sting.

Limit counterfactual thinking.

When you catch yourself imagining the “what ifs,” gently redirect your mind to the present moment. Mindfulness practices, like meditation or even simple breathing exercises, can help reduce rumination.

Take corrective action when possible.

Some regrets can be eased by making amends or trying again. Didn’t finish school? Maybe it’s not too late to take a class. Never apologized to a friend? A message today might still matter.

Focus on future choices.

The best antidote to regret is living intentionally in the present. Instead of wishing you had chosen differently yesterday, ask: What choice can I make today that my future self will thank me for?

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The Gift Hidden in Regret

While regret is painful, it’s also a sign that we care deeply about our lives and our choices. People who never feel regret often struggle to learn from mistakes or build empathy for others. Regret reminds us that our decisions matter, and that our lives are interconnected with those around us.

The real challenge is not erasing regret but transforming it. By seeing it as a teacher rather than a tormentor, we can use it to grow wiser, kinder, and more intentional.

In the end, regret may always whisper from the past—but it doesn’t have to drown out the voice of the present. And sometimes, learning to live with regret, instead of against it, is the most freeing choice of all.