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Category 3

The what-ifs: when replaying the past holds you back

What can I do when the what-ifs about something that happened keep holding me back?

Updated 6 October 2026 · 8 min read

The short answer

A what-if points at a feeling not yet felt, about a loss or a choice. Arguing with it keeps a person circling; meeting it with kindness opens the way to that feeling. In one small study of widowed people, self-blame, not regret, went with heavier grief. Kindness toward yourself is where acceptance and moving again begin.

Here is what I would tell you if the replaying comes with very heavy, lasting grief: take it to a therapist who works with grief. The same goes for any replaying that has stayed that heavy and gets in the way of daily life. If you are thinking about not being alive, please reach someone now. The help box near the end of this page says how.

A question about the past that keeps coming back

How it works

A what-if goes back to a moment and runs it again with a different ending. "If I had called sooner." "What if I had noticed." The mind goes back because what happened mattered, and because something in that moment has not been felt all the way through.

Here is the loop. A what-if compares what happened with how it should have gone, and it never arrives anywhere. Researchers call a repetitive, passive focus on distress rumination, and they split it in two. Brooding is a passive comparison of your situation with a standard not reached. Reflection is a purposeful turning inward to understand or solve a problem. In one community study, brooding went with more depression a year later, and reflection, tentatively, with less.

Looking back is not the trouble. A what-if is brooding: it circles the moment and never lands on the feeling inside it.

Why the what-ifs hold you back

Why it matters

A what-if comes first from caring: the mind goes back because someone or something mattered, a person, a plan, a job, a choice, and because the future you wanted from that moment did not arrive. Sometimes it also catches on something older, a habit of self-blame that was there before what happened. Then it becomes a loop: the same question, the same verdict, the same knot. Either way, it comes back because the feeling under it has not been met, and meeting that feeling without avoiding it is worth doing.

The loop has a cost. In a diary study of bereaved adults, days with more repetitive thinking about the loss were heavier days, and more so for people whose grief was more severe. A review of grief that stays intense linked avoiding the inner experience of a loss, and repetitive brooding about it, with grief that lasts longer.

Regret and self-blame are not the same, and after a death only one of them went with staying stuck. In one small study of widowed people, regret, wishing things had gone differently without blaming anyone, was not linked with grief or depression. Self-blame, holding yourself at fault, went with heavier grief at the start and a slower easing afterwards.

What turns a what-if from a loop into processing is self-compassion. Self-compassion here means what one theory paper means by it: kindness in place of harsh self-criticism, seeing your pain as part of shared human experience, and holding a painful thought in balanced awareness. In one study of people going through a divorce, those rated as more self-compassionate while talking about the separation had less intrusive, unwanted emotion about it, then and months later. In three studies outside grief, people who met a recalled regret with self-compassion reported more personal improvement, partly through acceptance.

Three places the what-ifs keep a person stuck

Where people get stuck

  1. Asking why. Ask what happened and how, not why. "Why" promises an answer the past cannot give. In experiments outside grief, abstract "why" thinking after a failure or a distressing film was followed by slower recovery of mood and more intrusive memories; concrete "what" and "how" thinking was not. Turning inward to understand is a different thing, and there is nothing wrong with it. The passive loop is the thing to step out of.
  2. Hearing a wish as a verdict. "I wish I had" and "it was my fault" can feel like the same thought. They are not. The study of widowed people above measured them apart, and only self-blame went with the course of grief. More on that in Guilt, shame and the inner critic.
  3. Fearing that kindness means not caring. Going easy on yourself can feel like letting the past off the hook. This fear is what keeps the loop running. In short experiments outside grief, people given a brief self-compassion prompt after a wrong they had done or a failed test reported more motivation to make amends, avoid repeating it or study for a retest than people given a self-esteem prompt or none.

When replaying is worth taking to someone

Any replaying that stays very heavy and gets in the way of daily life is worth taking to a doctor or a therapist.

Replaying that comes with grief that has stayed very heavy, blame of yourself that does not ease, or images that keep coming back is worth taking to a therapist who works with grief.

For grief that stays very heavy, grief-focused therapy exists and has helped many people in trials. For heavy repeated thinking about a loss, one small trial has tested therapist-guided treatment.

If you are thinking about not being alive, please reach someone now. The help box near the end of this page says how. For immediate danger, contact local emergency services.

A what-if deserves kindness, not an answer

In my view

A what-if is an invitation, not an accusation. The mind goes back over a loss, a choice or a moment because it mattered, and because something in that moment is still waiting to be felt. Most of the time, what is waiting is plain sorrow or disappointment at something real. Sometimes it is older than what happened: a habit of blaming yourself, of carrying it alone, of believing you should have known. A loss or a setback can bring that habit to the surface, and then it is an opportunity too.

Nobody has to win the argument with the past before they are allowed to accept themselves. Most what-ifs cannot be answered, and they do not need to be. They need to be felt, with kindness, until their grip loosens.

A wish is not a verdict. "I wish I had" deserves respect. "It was my fault", held for years, is a pattern, and a pattern can be met.

When a person meets a what-if with kindness, two things follow. They accept themselves, including what they did and did not do. And they find the energy for the next step that is theirs, out of care rather than guilt. That is a healthy adult: someone who can hold the past without being run by it.

Where the research on the what-ifs is thin

Where the research is thin, or disagrees

No study I found is about what-ifs after a loss; the link from each study here to what-ifs is mine. The grief studies measured links, not causes, and are about a death, not what-ifs about a breakup, a job or a choice; most of the self-compassion research was done outside grief. Whether moving from "why" to "how" makes a difference for bereaved people has not been tested.

Noticing what a what-if asks

One thing you might notice

If a what-if comes back, you might notice whether it asks why, or asks what happened and how. You might also notice whether it sounds like "I wish" or like "it was my fault". Either is information, not a verdict. If noticing makes it louder, you can stop.

What a session does with a what-if

How Feelings Buddy fits

Feelings Buddy is built for working through feelings with self-compassion, toward self-acceptance and self-motivation. A hard feeling is the obstacle, not the destination.

A session is an AI working from written instructions, so it can get them wrong. Its instructions say to:

  • meet a what-if with compassion, neither arguing with the harsh voice nor agreeing with it, and help the person find a kinder voice of their own.

Nothing in its instructions runs or imitates the therapist-guided treatment above.

There is no diagnosis, and a session carries nothing about risk into a later session. No one reads the conversation as it happens.

No study has tested Feelings Buddy. How a session works, step by step

Frequently asked questions

Is asking what and how, instead of why, a way to get unstuck?

Yes. It is the first step out of a what-if. "Why" circles. "What happened" and "how" land on something you can feel. In experiments with people who were not bereaved, abstract "why" thinking about a distressing event tended to prolong low mood, and concrete "what" and "how" thinking did not.

Is regret the same as blaming myself?

No, and the difference matters more than anything else in this article. Regret is wishing things had gone differently. Self-blame is holding yourself at fault. In one small study of widowed people, self-blame went with heavier grief and a slower easing of it, while regret was not linked with grief or depression. Regret deserves respect; self-blame deserves a second, kinder look.

Can I accept myself while the what-ifs are still there?

You can. Acceptance comes first, not last. A what-if does not have to be answered before you count yourself worth caring for. In three studies outside grief, people who met a recalled regret with self-compassion reported more personal improvement, partly through acceptance.

Is being gentle with a what-if the same as not taking it seriously?

No. Kindness is what makes it possible to take a what-if seriously. Harshness makes a person look away; kindness lets them look, own their part and act. In short experiments with students and online adults, people given a brief self-compassion prompt after a wrong they had done or a failed test reported more motivation to make amends, avoid repeating it or study for a retest.

When is replaying worth taking to a therapist?

When it comes with grief that has stayed very heavy, blame of yourself that does not ease, or images that keep coming back. Grief-focused therapy exists and has helped many people in trials, and one small trial has tested therapist-guided treatment for grief with heavy rumination. Any replaying that stays that heavy is worth taking to a doctor or a therapist. If you are thinking about not being alive, please reach someone now; the help box on this page says how.

If this is heavier than an article can hold. Some grief needs a person, not a page. If it has stayed as heavy as the first weeks for a long time, if daily life has stopped working, or if you are thinking about not being alive, please reach someone now.

The crisis lines are at the foot of this page.

A family doctor, or a therapist who works with grief, can help you work out what kind of support fits.

Further reading (13 sources)

The tier and grade after each source come from my own evidence file, not an independent panel. The note under each source gives the study details the article leaves out.

  1. Nolen-Hoeksema S, Wisco BE, Lyubomirsky S (2008). Rethinking Rumination. Perspectives on Psychological Science 3(5), 400-424. DOI 10.1111/j.1745-6924.2008.00088.x. Tier 2, weak.

    Note: a review of research on rumination, used here only for its definition; not about grief.

  2. Eisma MC, Franzen M, Paauw M, Bleeker A, Aan Het Rot M (2021). Rumination, worry and negative and positive affect in prolonged grief: A daily diary study. Clinical Psychology & Psychotherapy. DOI 10.1002/cpp.2635. Tier 2, weak.

    Note: 62 bereaved adults, of 113 surveyed, kept a diary twice a day for 10 days; higher-educated women were over-represented; observational.

  3. Eisma MC, Stroebe MS (2021; published online 2020). Emotion Regulatory Strategies in Complicated Grief: A Systematic Review. Behavior Therapy 52(1). DOI 10.1016/j.beth.2020.04.004. Tier 1, moderate; abstract read.

    Note: 64 studies of grief that stays intense; most were surveys, and the laboratory results were mixed.

  4. Watkins ER (2008). Constructive and unconstructive repetitive thought. Psychological Bulletin 134(2), 163-206. DOI 10.1037/0033-2909.134.2.163. Tier 2, moderate.

    Note: a narrative review by one author of experiments with students, people with low mood and depressed patients, not bereaved people; mood measured over hours to days.

  5. Treynor W, Gonzalez R, Nolen-Hoeksema S (2003). Rumination Reconsidered: A Psychometric Analysis. Cognitive Therapy and Research 27(3), 247-259. No DOI recorded in my evidence file. Tier 2, moderate.

    Note: community adults interviewed a year apart; each of the two parts rests on five questionnaire items; reflection went with slightly more depression at the first interview, and its later result appeared only once brooding was taken into account.

  6. Stroebe M, Stroebe W, van de Schoot R, Schut H, Abakoumkin G, Li J (2014). Guilt in Bereavement: The Role of Self-Blame and Regret in Coping with Loss. PLOS ONE 9(5). DOI 10.1371/journal.pone.0096606. Tier 2, weak.

    Note: 60 bereaved spouses in one region of southern Germany, mean age about 53, followed over two years; five questions for each kind of guilt; correlational, so self-blame may mark a harder grief rather than cause it.

  7. Neff K (2003). Self-Compassion: An Alternative Conceptualization of a Healthy Attitude Toward Oneself. Self and Identity 2, 85-101. DOI 10.1080/15298860390129863. Tier 2, weak.

    Note: a theory paper with no data, so its expected benefits are predictions, not results.

  8. Sbarra DA, Smith HL, Mehl MR (2012). When leaving your ex, love yourself: observational ratings of self-compassion predict the course of emotional recovery following marital separation. Psychological Science. DOI 10.1177/0956797611429466. Tier 2, weak; abstract read.

    Note: 109 adults going through a divorce, not a death, followed up to nine months; one correlational sample; no intervention tested.

  9. Eisma MC, Boelen PA, van den Bout J, Stroebe W, Schut HA, Lancee J, Stroebe MS (2015). Internet-Based Exposure and Behavioral Activation for Complicated Grief and Rumination: A Randomized Controlled Trial. Behavior Therapy 46(6). DOI 10.1016/j.beth.2015.05.007. Tier 2, weak; abstract read.

    Note: 47 participants with high dropout; those who finished showed no group differences; the abstract does not describe what the exposure involved.

  10. Shear K, Frank E, Houck PR, Reynolds CF (2005). Treatment of complicated grief: a randomized controlled trial. JAMA. DOI 10.1001/jama.293.21.2601. Tier 2, moderate.

    Note: one randomized trial with 95 participants, 83 of them women; about half of those treated did not respond.

  11. Wittouck C, Van Autreve S, De Jaegere E, Portzky G, van Heeringen K (2011). The prevention and treatment of complicated grief: a meta-analysis. Clinical Psychology Review 31(1). DOI 10.1016/j.cpr.2010.09.005. Tier 1, moderate; abstract read.

    Note: 14 randomized trials of varying quality, pooled; it predates newer trials.

  12. Breines JG, Chen S (2012). Self-Compassion Increases Self-Improvement Motivation. Personality and Social Psychology Bulletin 38(9), 1133-1143. DOI 10.1177/0146167212445599. Tier 2, moderate.

    Note: four short experiments with undergraduates and online US adults; every outcome measured within one session; not grief.

  13. Zhang JW, Chen S (2016). Self-Compassion Promotes Personal Improvement From Regret Experiences via Acceptance. Personality and Social Psychology Bulletin 42(2), 244-258. DOI 10.1177/0146167215623271. Tier 2, moderate; abstract read.

    Note: three studies, not in bereaved people; the abstract gives no sample sizes or populations, and improvement was reported or rated within the studies.

Updated 2026-10-06.

Feelings Buddy is an AI-guided tool built for working through feelings, with self-compassion, toward self-acceptance and self-motivation. It is not therapy, not a crisis service and not medical or psychological advice, and it does not replace care from a qualified professional. For adults 18 and over.