It can take considerable amounts of courage to open up a conversation and make amends for something we regret in our past.

Wondering how to apologize to someone you hurt a long time ago without opening Pandora’s box? Wondering if apologizing will be too difficult or intrusive after so much time has passed? Do you worry about how the recipient might receive your apology?

‘The best time to plant a tree is twenty years ago. The second-best time is now,’ as the old saying goes. Maybe the best time to apologize is now.

We can all remember a cringing moment in the past when our actions or words inflicted pain upon another person. The memory fills us with shame. We behaved in a way we now regret. We said. We did. We didn’t do. Maybe we knew it at the time, maybe time has shone a spotlight on our mistake. Maybe the years have withered and exposed our part in an unfortunate event. Whatever the reason, sometimes the thought of making amends becomes inescapable. It is time to apologize.

How to apologize to someone you hurt a long time ago?

A good apology, one with good strong bones, is the same whether time has passed or not. The key to a good apology lies not necessarily in the timing but in the apology, itself.

We have all been victims of an insincere apology.

Insincere apologies are often thinly veiled ways to reverse blame.

Often, insincere apologies are opportunities to explain ourselves or justify ourselves or excuse ourselves. If the tone of an apology is weaselly, it can leave the recipient feeling more hurt and angry than before. If there is no remorse in the apology, an apology is likely to do more harm than good.

Get the apology right, and the dance of apology and reconciliation can begin.

A good apology can be a watershed moment not only for a relationship but for the individuals as well. A good apology can set both parties free.

Many well-intentioned people want to apologize and honestly don’t know how.

Well-meaning people say, ‘I’m sorry’ and yet, a relationship remains icy.

A good apology isn’t just about saying the right thing and avoiding the wrong thing; it’s more complicated than that, but it sure helps to know the difference.

Want to know how to apologize to someone you hurt a long time ago? Let’s hit the basics.

Eight ways to ruin an apology:

1. Using the word ‘but’. You are going for heartfelt, sincerity. Adding on a ‘but’, no matter how small, signals an excuse. It nullifies the original message. When you say, ‘I am sorry for doing this, but ….’ It says that you regret doing what you did, however your excuse makes your actions understandable. This is not an apology. This makes an apology false.
2. Using the phrase, ‘I’m sorry you feel that way’. A sincere apology focuses on your actions, not the other person’s response. ‘I’m sorry you got so angry. I had no idea you were so sensitive,’ is disrespectful. It implies fault with the other person. This is not an apology. This is avoiding responsibility.
3. Using ‘if’. Another tiny, but dreadful word in any apology is the word ‘if’. Like it’s friend, ‘but’, ‘if’ can slash any apology. ‘I’m sorry if what I said hurt your feelings,’ is a non-apology. ‘I’m sorry I was insensitive. I promise you I will not make that mistake again,’ begins to heal. Yes, these tiny words seem negligible, but if used, they will turn your apology into a ‘sorry-not-sorry’ in a heartbeat.
4. Pleading for forgiveness. Asking for forgiveness at the end of an apology, no matter how sincere the apology is, is a quick way to nullify your heartfelt apology. Asking (or worse, demanding) forgiveness makes the apology about you, your needs, your neediness. Instead of apologizing and then asking (or begging) for forgiveness, a better option might be to say something like, ‘I know what I did was serious. I could understand if you were mad for a long time. If there is anything I can do to make it better, please let me know.’ Allowing someone to sit with their emotions, their anger and pain is respectful. Yes, we all want to be forgiven. Forgiveness comes in time. A true apology may need time and space to set. Asking for forgiveness is not part of an apology. Forgiveness requires time.
5. Serving to soothe your own guilt. Often, we feel called to make amends for our behavior only to make ourselves feel better. If your apologies might traumatize another person, work on forgiving yourself, instead. The purpose to apologize is to soothe the other person. If you are going to tear open a wound simply to explain yourself, advance your recovery or calm your self-loathing, skip it. Injuring another person is not an apology. Self-forgiveness is what you need.
6. Making sweeping apologies. When we know we’ve damaged a relationship, but are unsure why it is easy to make sweeping generalized apologies in order to restore peace. ‘I don’t know what I did wrong, but I’m sorry,’ is not an apology. While it may seem as if you are taking responsibility, it is an un-apology. It is an insulting way to avoid responsibility and dialogue. Sweeping, all-inclusive apologies which are intended to avoid conflict or self-inspection are not apologies. Understanding a person’s experience is.
7. Over-apologizing. If apologizing makes the other person feel worse, it is a non-apology. It is possible to overdo an apology. Apologizing, crying, overemphasizing your feelings, repeatedly bringing up your error, dramatically explaining how you will never forgive yourself, telling tales of emotional pain and distress and needing the recipient to comfort you is not an apology. It is overkill. It makes it about you. It makes the recipient obligated to sooth you. It crowds them and can make a person feel disempowered. A true apology may include expressions of remorse and guilt. A person’s sorrow may be deeply felt. Overdoing apologies aren’t apologies. They are cries for help. Failing to dial down the intensity of an apology screams ‘your suffering’ and it does not allow the recipient to heal. Apologize sincerely. Then seek therapy for ways to cope with your own deep grief, regret, and guilt.
8. Offering an ‘in word only’ apology. Restitution is part of an apology. Apologizing in word only is not a real apology. Take immediate and thoughtful action after a heartfelt apology. Spilling a gallon of paint on the floor, apologizing but failing to help clean it up or offering to pay damages, is offensive. It is a non-apology.

Six ways to nail an apology:

1. Less is more. Bringing up every detail of said event isn’t going to help. The longer we speak when we feel nervous, the more likely we will be to ramble, increase our intensity and sharpen our tone. Keeping apologies succinct can help us keep our tone and our body language in check. Apologies do not require a re-hashing of events.
2. A true apology includes personal responsibility, guilt, and remorse. Tell the person that you know your actions hurt them. Explain that you understand why your actions were upsetting. Instead of saying, ‘I’m sorry you were angered by my comments during the meeting,’ try, ‘I’m sorry I kept interrupting you during the meeting. It must have been frustrating. I get it. It won’t happen again.’
3. Apologizing comes with a hearty dose of vulnerability. Apologizing requires a leap of faith. You cannot control how someone will react. A sincere apology does not evade, but accepts responsibility. A heartfelt apology accepts that time and subsequent conversations may be needed to grow through the pain. An apology is the first step, not a tidied bow on top of a package. Give the person time and space to anchor their feelings. Give them permission to talk about it at a later date.
4. Apologies are more about relationships and less about wrong/right. Every sincere apology is an olive branch extended. It is about friendship, integrity, parenting, loyalty, love, leadership. Lead with your heart, not with your ego. It isn’t about being right, it is about preserving the relationship.
5. A sincere apology is a gift to the other person. A true apology validates another person. It affirms their feelings. It gives them space to heal. It helps them make sense of a painful experience. Offering a sincere apology can free a person from years (or a lifetime) of anger, bitterness, and pain.
6. Tone, compassion, listening intently, body language and eye contact matter. Sometimes, a good apology means listening to the recipient’s responses without becoming defensive. A good apology heals wounds, it doesn’t tear one open.

The two most healing words in the English language are ‘I’m sorry.’

If you offended someone yesterday or years ago, it is never too late to apologize, to open the door to further conversations. A good apology is only the beginning. A good apology establishes a future. A good apology fosters healing.