Source: Life 
“I’m sorry.” Two simple words and yet two of the hardest to say. We easily utter them in response to trivial matters like accidentally jostling a stranger on the subway or giving the cashier the wrong change. Yet in important matters and to those who mean the most to us, we can find ourselves practically choking on the words. But the inability to apologize can critically wound all of our relationships, from home to work. Learning how to properly apologize is a necessary step in moving from boy to man.
Why We Don’t Apologize
Pride. Apologizing can be particularly hard for men because it involves the admittance of fault. It’s hard to say that we messed up. That we were wrong. Our pride gets in the way.
Embarrassment. If we messed up royally, doing something truly boneheaded even though we knew better, it can be difficult to talk about it to the person we hurt or let down. We feel stupid and would rather pretend like it didn’t happen.
Anger. Things that need apologizing for are rarely a one way street (more on this later). We probably did something wrong, but the other person probably did too. And sometimes our anger over how they offended us is so great that we justify what we did and can’t get past it to apologize.
The antidote to all 3 obstacles? Humility. The reason we put up these walls is that we have an overinflated view of our true selves. We’re always right; we always have it together. But it ain’t true. We’re human. We mess up sometimes. You have to accept your imperfection as a part of life. Suppressing it will cut you off from others. Embracing it will allow you to grow as a man.
When to Apologize
Even when it’s not fully your fault. There is a breed of man who will not apologize unless he feels 100% at fault for something. “But it’s not my fault!” is his battle cry. He’s not at fault for throwing away an important document at work because no one specifically told him to hold onto it. He’s not at fault for hurting his girlfriend’s feelings because she shouldn’t have been listening to his conversation with his friends.
But almost no situation is 100% one person’s fault. If your wife flew off the handle and called you some cutting things for seemingly no reason, it’s not because she’s just an ice princess; she’s hurt because you’ve been working 80 hour weeks and not spending enough time with her.
Even if the fault split is something like 1%/99%, you still need to work hard to humble yourself and come to an understanding of what that 1% is rooted in. Don’t live your life as though every day you’re pleading your case before an imaginary court, presenting evidence for why you are not at fault and are innocent as charged. It’s not as important to be right as it is to have healthy relationships with others. Would you rather be right than give up your relationship with someone? Would you rather be right than lift the hurt feelings from another? Being self-satisfied in your justice offers little benefit but the feeling of smugness. And smugness won’t keep you warm at night.
You don’t have to apologize for what truly wasn’t your fault, but you can find the things, no matter how small, that you could have handled better. Once you apologize for those things, that will get the ball rolling for the other person to own up to their mistakes. Don’t let pride stop you from being the bigger person and taking the initiative.
Even when you haven’t been caught. As a boy, did you ever break something and then run away, hoping that no one would notice, and that if they did, they wouldn’t connect the crime back to you? This is how a child handles his mistakes. A man owns up to his mistakes and offenses whether or not he thinks he will be held accountable.
Quickly. Apologize as soon as you can after making a mistake or committing an offense. The longer you wait, the more resentment is going to build up on both sides, the harder it will be to make the first move, and the more awkward the situation will become. Be a man and nip it in the bud.
When Not to Apologize
For your beliefs. If you offend someone by standing up for your beliefs because you failed to debate like a gentleman  and ended up being snarky, attacking the person personally, or generally acting like an ass, then you should apologize for your boorish behavior. However, if you’ve made a completely respectful argument in favor of your position and a person is simply offended because of the nature of your beliefs, then you should never apologize for that. Don’t be sorry for what you hold near and dear to your heart.
For not meeting unreasonable expectations. You know this guy. His girlfriend expects him to kowtow to her every wish and treat her like a princess 24/7. When he fails to do this, she expects him to grovel in repentance. This isn’t being sensitive, it’s being a whipped weenie.
For everything. This man apologizes for his appearance, for things that aren’t his fault that no one is saying are his fault, and for perceived shortcomings that no one notices until he brings them up. And he keeps on apologizing. Over and over again when everyone else has moved on. Being a compulsive apologizer is highly emasculating and instead of getting you into people’s good graces as you might assume, will simply erode their respect for you.
How to Apologize
Write it if you can’t say it. Sometimes our embarrassment or pride prevents us from going in person to apologize to someone. While a face to face apology is always ideal, if you absolutely can’t do it, then it’s better to get it out then not do it at all. And sometimes a letter or note is actually a superior medium to talking because it allows you to express all of your feelings without forgetting what you want to say or running the risk of setting off another argument.
Use humor when appropriate. Some self-deprecating humor can break the tension and cause you both to laugh. I’ve found that drawing little cartoons of me and my mishap can instantly dissipate my wife’s anger. Note that I said, when appropriate. If you cheated on your girlfriend, don’t crack jokes or make cartoons about it. “And see in this panel, that’s me making out with your best friend.”
Be sincere. This is the cardinal rule of apologies. An insincere apology is in some ways worse than no apology at all. The person’s hurt over your offense will merely be compounded by their anger at your hypocrisy. An insincere apology may take the form of saying you’re sorry but saying it in such a way that your lack of contrition is patently manifest. Another form is the famous “I’m sorry you’re sorry” apology. This apology admits no fault but pretends like saying you’re sorry that the person was hurt or is angry is still pretty big of you. Don’t bother; it will make the person want to stab with you a trident.
Take complete responsibility. Never, ever make any excuses while you’re apologizing. They instantly ruin the weight and sincerity of your confession. Don’t use any “buts.” As in “I’m really sorry that happened, but….” A man takes full responsibility for his mistakes.
Express your understanding of why you were wrong and the weight of your mistake. A person wants to know that you fully understand the seriousness of the situation, that you have thought through exactly why what you did was wrong and the full consequences of your actions. Nobody wants to hear an apology from someone who clearly doesn’t know why they’re in the wrong but feels like apologizing is what they’re “supposed” to do.
Offer to make restitution. This is a key part of the apology process. You should almost always offer to try in any way you can to make up for your misdeed. This obviously isn’t always possible. If you break your wife’s 5th generation family heirloom vase, you can’t go to Target and buy a replacement. But if a situation can be fixed and rectified, that you should pledge to do whatever it takes to do so.
Pledge better behavior in the future. Notice that I said pledge and not promise. While some would argue that if you’re really sorry, you’ll never make the same mistake again, our failings as human beings dictates otherwise. I might be truly sorry for losing my temper on someone, but I’m pretty sure that no matter how hard I try, it’s probably going to happen again somewhere down the line. When you promise someone that something is never going to happen again, you’re setting yourself up for a huge rift to develop if it does. The person will be justifiably doubly hurt, because after all, “You promised!” There are of course some things that you can be almost 100% sure you’ll never do again, and if you feel absolutely confident in that, then make a promise. But generally you should simply pledge that you’re going to be working hard on fixing whatever personality or behavioral faults led to your current offense. You can promise that you’re going to be making an effort to change and turn things around.
Prove your contrition with your actions. In the end, words will matter very little if your actions don’t match them. After you’ve apologized, stop dwelling on it. Simply start acting in a way that demonstrates the sincerity of your apology.
Move on. Once you’ve given your sincere apology, don’t apologize again. Having you continually apologize may be what the offended party thinks they want from you and it may make them feel better in the short term. But in the long term, it’s going to ruin the relationship. If you continue to grovel then you’ll always be in the inferior position instead of having the person treat you like an equal. Deep down they won’t be respecting you as a man. Either the person accepts your apology or they don’t. If they do, then there’s no need to keep groveling. If they don’t, then the person doesn’t trust you and the relationship has other problems that need to be fixed.