How To Make Someone Cry In A Goodbye Letter Guide

Writing a letter is one of the best ways to convey your feelings. Without leaving your confines or having a face-off with someone, you can express your feelings from your bedroom and make someone cry.

So, how can you create an effective goodbye letter that will make someone cry? We’ll find out soon enough. It only takes a few minutes to leave a meaningful message, but the impact is long-lasting. It doesn’t matter if your end-of-life letter is long or short; what matters is that you compose it.

Before we show you how to make someone cry in a goodbye letter, let’s talk about when it is best to write a goodbye letter to someone.

When Is It Best To Write A Goodbye Letter To Someone?

Before you write a goodbye letter you need to be convinced that you are doing it at the right time. Let’s take a look at when its best to write a goodbye letter:

1. When you’re breaking up with them

Suppose you want to end a relationship with your lover or any other person. This could e mutually or forcefully. You may want to write a goodbye letter to make the person feel your potential absence.

Although you two did not survive, they will have recorded memories to reflect on and remember the beautiful times. Nothing can compare to seeing your handwriting for the last time.

2. You’re leaving a situationship

A ‘situationship’ exists between “just friends” and “dating.” It’s when you and your partner have strong feelings for each other but haven’t made it official yet. Though you two may not be dating, it hurts a lot more when it’s over.

It’s passionate but fragile, genuine but without a title to prove it. And sometimes you knew it would end from the start, yet you still jumped in headfirst. And when it’s over, you’re left with “what could have been” and many what-ifs.

So now you want to end the relationship with a goodbye letter to make them cry and think about you in the future as the one who got away.

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3. You’re bidding farewell to a friend or friendship

Suppose you’re saying your goodbyes to a friend you won’t see again for obvious reasons like relocation or bridge of relationships. In that case, you can decide to express yourself in your goodbye letter and cry if necessary.

4. You wronged someone

If you have done something wrong to someone and you are full of regret and weary, you can decide to write a goodbye letter to take the worries off your chest and see what comes out of it.

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When You Shouldn’t Write A Goodbye Letter

Sending someone a goodbye letter is not always the solution to the problem. Unless you write a purifying letter that you don’t plan to send to someone and want to heal yourself by pouring your thoughts on paper.

Let’s take a look at when not to write a goodbye letter.

1. When someone cheated on you

Cheating is unethical on so many levels. They cheated on and disrespected you regardless of how or why they did it. You can forgive them and move on with your life, but they don’t deserve to read your farewell letter.

They weren’t thinking about you when they cheated on someone else, so don’t give them the notion that they’re living rent-free in your head. You must move on and leave them in the past where they belong.

Also, why bother writing and delivering a farewell letter to a cheater? Pack your belongings and depart. You don’t even need to notify them that you’re leaving. Did they inform you that they were planning to cheat?

2. If someone suddenly stops talking to you

Even if there are numerous reasons why someone stopped messaging you, they did so for a purpose. Don’t embarrass yourself by drafting a lengthy parting letter. They didn’t even bother to say goodbye to you.

So why should you do something like that for them? What makes you think your goodbye letter will matter, let alone make them cry if they care so little about you that they can depart without telling you why?

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3. The person asked you not to contact them

If they have requested that you leave them alone, write and send this letter at your own risk. People don’t always mean it when they urge you to go for good, but most of the time, they do. So exercise caution when sending a letter to someone who does not wish to receive one in the first place.

Have some self-esteem and understand when to take rejection. Your letter may be discarded if you disregard their request to be left alone. Worse, it will destroy any future chances you have with them.

How To Make Someone Cry In A Goodbye Letter

Now that you’ve decided to compose this heartbreaking farewell letter, it’s time to get started. Genuine tears can only be shed if you know the person on the other side of the letter. However, if you’re writing them a farewell letter, you probably know them very well.

Let’s go on to how to make someone cry in a goodbye letter.

1. Which do you prefer, writing or talking?

Some people find it challenging to convey their emotions vocally, so they write them down instead. You’d like to communicate your feelings in the most natural way possible. Don’t try to make a statement or go out of your comfort zone with how you say goodbye. Do what feels right to you.

Write if you feel comfortable doing so. But if it’s not your thing, don’t push it. There are plenty of other meaningful ways to say farewell.

2. Know precisely why you’re writing the letter

Are you writing to get closure? Do you want to vent? Do you want to say things to this individual that you couldn’t communicate in person? Do you want to beg forgiveness to go on? Do you expect a response from this person?

You must know what you want so that you do not express too much or too little when writing. A text message can be unsent, but an email or letter cannot be unsent or edited. Make sure you will not regret or wish to change anything you have written.

3. Write at your own time and pace

Yes, you want an emotional letter. Is it wise to write it while violently sobbing on the bedroom floor? You can, but the outcome may not be what you expect. When we are upset, we frequently exaggerate our discomfort. And when we go back and read the lines we penned at those moments, we may grimace.

The best way to do it is to write when you want to but then go back and revise it when you’re in a better mood. When your mind is more precise, you can better analyze the emotions you experienced. You might even devise better ways to phrase things or cross out unnecessary lines.

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4. Be honest

If you want the individual reading your letter to experience your emotions, write it from the heart. Everyone can tell when a letter isn’t written from the heart. Even to the untrained eye, it is clear.

If you’re not crying or feeling emotional when writing the letter, neither will the person who receives it.

And don’t even think of copying lines from poetry or a love novel for dramatic effect. Someone who knows you well enough can tell those are not your words. Compose the letter as if you were speaking to the recipient as if they were standing right before you.

5. Be concise

You can write five pages if you want, but it’s more potent if you can communicate everything you want in the fewest words possible.

A letter should not shock the reader, nor should it make them feel like they are reading a novel. Don’t go into much detail, and don’t overanalyze. Keep it brief and to the point.

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6. Don’t play the victim

If you want your goodbye letter to make them cry, don’t spend an entire page criticizing them for everything. It’s over, no matter who was to blame. Blaming them serves no purpose.

If you choose the high road and do not detail all of their flaws, the letter will be more compelling. Because this is a farewell letter, say goodbye.

7. Focus on you

A goodbye letter is supposed to clearly explain what got you upset in the past and why you are saying goodbye.

Even though you’re writing to them, this letter isn’t about them. They already know how they feel; now is your turn to express yourself. They will undoubtedly cry when they read this goodbye letter and realize how devastated you are.

8. Cry out your heart

Many of us are terrified of appearing weak, so we hide our feelings. It’s pointless to do so here. If you’re writing a letter, it indicates that your emotions are strong and overflowing.

You don’t have to be ashamed of your emotions! Being vulnerable is the best method to write a goodbye letter that makes someone cry. Show them your true self.

Don’t just say things to make yourself appear “strong” and “cool” if that’s not how you feel on the inside. Tell them if they did something that genuinely wounded you or you’re ashamed of what you did to them.

9. Don’t get stuck on the format

No one is a born emotional writer, it all comes from a place of outburst. When writing, ensure you say your peace regardless of the conventional letter-writing format.

10. The channel you choose to send the letter through doesn’t matter

It makes no difference if you write them a letter, type it, and send it by email or text message. A letter is still a letter. You select the channel via which you want them to receive it, one with which you are most comfortable.

If you send it online, they will always have a virtual copy. If you write them a handwritten note and hand it over, you risk their losing it or pouring coffee on it, but it will be more valuable because it is unique. So go ahead and pick whatever you want.

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11. Mention good memories

If you want your goodbye letter to make them cry, emphasize the nice times you’ve had with them. Don’t only focus on the sad parts. Good recollections are typically the most painful.

When we’re attempting to move on from an ex, we don’t think about the fights and breakups. The memories that haunt us will be the laughing and kissing and the shared stories. So bring them up if you want the person to become emotional.

12. Focus on details

When trying to paint an emotional picture that should eventually make the recipient cry you need to tell a story about how their actions affected you. If possible, point out what they said to you.

Take them on a journey through time and show them what may have been. All of the what-ifs will also haunt them.

13. State why you’re saying goodbye

They must understand why you are saying goodbye. What occurred? Why are you deciding to leave now?

You must respond to these questions for them. Otherwise, you’ll leave room for misunderstanding. You must be in command of your farewell letter.

14. Lastly, say goodbye

Please make sure you say goodbye and send them your best wishes at the end of the letter. A chapter in your life is not entirely closed when someone writes you a goodbye letter but does not end it.

Don’t close the chapter if you want them back. If you wish to move on, make it clear that this is your final goodbye.

FAQs On How To Make Someone Cry In A Goodbye Letter

What is the most painful goodbye?

The most painful goodbyes are the ones never said, but the heart already knows it’s over.

What do you say in a final goodbye message?

You can use these phrases in a final goodbye message; I love you, I forgive you, I’m sorry, or Thank you.

Why do people write goodbye letters?

Writing a goodbye letter allows you to validate your relationship one last time

How do you write an emotional letter?

Communicating your thoughts and feelings is essential while writing a letter to your emotions. To do so, ask specific questions about how this feeling has recently manifested in your life. Then, write your responses as if you were speaking to the emotion.


We hope this article on how to make someone cry in a goodbye letter was helpful. Be honest, strong, and direct, and you will not fail. Good luck! 


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