How to Write a Heartfelt, Touching Goodbye Letter & Make Someone Cry

Writing a letter is the best way to express your feelings. So how do you write a successful goodbye letter that makes someone cry?

Do you want to make someone cry in a goodbye letter? You don’t need to practice the speech in front of your mirror or fight your anxiety when you approach them. You can write a meaningful letter in the comfort of your bedroom without any pressure to get your feelings across.

[Read: Here’s what I’ve always wanted to say in a letter to my ex]

When to write a goodbye letter to someone – The best scenarios

Before you get your pen and paper out, you need to know when you should write a goodbye letter to someone.

1. You’re breaking up with them

Maybe you have to break up with this person. It might have ended already. It could be a mutual decision, or one of you decided to call it quits. You might want to write this letter to officially say goodbye, hoping you can make your ex cry for all that you’ve been through together.

Although you two didn’t last, they’ll have memories written in words to look back to and reminisce about the good times. Nothing is more emotional than seeing your handwriting for the last time.

2. You’re leaving a situationship

A situationship is somewhere in-between “just friends” and “dating.” It’s when you two have strong feelings for each other, but you don’t make it official yet.

A situationship is more serious than the talking stage, but you’re not boyfriend and girlfriend, so it tends to hurt a lot more when it’s over. [Read: Dating exclusively but not in a relationship? The grey area dilemma]

It’s passionate yet fragile, real yet there’s no title to prove it. And sometimes, you already knew that it was meant to be over from the beginning, yet you jumped in headfirst anyway. And when it ends, you’re left haunted by “what could have been” and many what-ifs.

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

[Read: Talking vs Dating – 16 ways to tell them apart & know your exact status]

3. You’re saying goodbye to a friend

Maybe you’re saying goodbye to a friend that you don’t know when you’ll see again. You could be moving to another country, or for some reason, you cannot be friends with them anymore.

They say friendship breakups are usually worse than relationship breakups. So get your feelings out in your goodbye letter, and cry if you have to.

[Read: 25 ex best friend quotes to deal with outgrowing or ending a friendship]

4. You did something wrong to the person

Maybe you’re the reason the relationship or friendship came to an end. Nobody’s perfect. In fact, everyone makes mistakes. So you might have done something wrong that you regret, and by writing this letter, you hope to clear things up one last time.

The person may or may not forgive you. Things may or may not go back to the way they were before. But at least you can get some weight off your chest.

[Read: Kissed your ex or made out with them? What it means & what to do next]

When to NOT write a goodbye letter – Don’t ignore this

Sending someone a goodbye letter is not always a good idea. Unless you plan to write a cathartic letter that you don’t intend to send to someone and just want to heal yourself by releasing your thoughts, here’s when to NOT write a goodbye letter:

1. The person cheated on you

Cheating is wrong on so many levels. No matter how they did it or why they did it, they still cheated on you and disrespected you. You may forgive them and move on with your life, but they don’t deserve the satisfaction of reading your goodbye letter.

They didn’t think about you when they cheated with someone else, so you shouldn’t give them the impression that they’re living rent-free on your mind. You need to get over it and leave them in the past where they belong.

Also, why waste so much effort writing and sending a goodbye letter to a cheater? Just pack your bags and leave. You don’t even have to tell them you’re leaving. Did they tell you they were going to cheat?

[Read: Who cheats more? Men, women & their specific needs to cheat]

2. The person ghosted you

Although there are many reasons why someone stopped texting you, they still did it for a reason. Don’t make a fool out of yourself by writing them a long goodbye letter. They didn’t even make an effort to say goodbye to you. So why should you do that for them?

If they care so little about you that they can just disappear without telling you why, what makes you think your goodbye letter would matter let alone make them cry?

[Read: Am I being ghosted? 25 signs you’re on the verge of being ghosted!]

3. The person asked you to not contact them

If they asked you to leave them alone, write and send this letter at your own risk. Sometimes, people don’t mean it when they ask you to go away for good, but most of the time, they do. So beware when you send a letter to someone who doesn’t want to receive one in the first place.

Have some self-respect and know when to accept rejection. If you ignore their wish to be left alone, your letter might end up in the trash. Or worse, it’ll ruin every chance you’ll have with them in the future.

[Read: How your self-respect in a relationship affects you & your love life]

The 14 most important steps on how to make someone cry in a goodbye letter

Now that you’re sure that you want to write this heartbreaking goodbye letter, it’s time to get started. You really have to know the person on the other side of the letter to get true tears going. But if you’re writing them a goodbye letter, you probably know them pretty darn well.

So, let’s not waste any more time. That goodbye letter isn’t going to write itself.

1. Are you better at writing or talking?

Some people just aren’t great when it comes to verbally expressing their emotions, so they choose to write them down instead. You would want to express your emotions in the most comfortable way.

Don’t try to make a statement or step out of your comfort zone with how you’re going to say goodbye. Do what feels right to you.

If you feel comfortable writing, then write. But if it’s not your thing, don’t force yourself. There are plenty of other meaningful ways to say goodbye. [Read: How to say goodbye to someone you love]

2. Know exactly why you’re writing the letter

Are you writing this to get closure? Do you just want to vent? Do you want to tell this person things you wouldn’t be able to tell in person? Do you want to ask for forgiveness so you can move on? Do you expect this person to write back?

You must know what you want, so when you write, you won’t say too much or too little. You can unsend a text message, but you cannot unsend or edit a sent email or an actual letter. Make sure you won’t regret or want to change what you wrote.

3. Write when you want to write

Yes, you want a heartbreaking letter. But is it wise to write it when you’re violently sobbing on the bedroom floor? You can, but it might not give you the result you’re expecting.

A lot of times, we overexaggerate our pain when we’re upset. And when we go back to read those lines we wrote in those moments, we might find them cringe.

The best way to do it is to write when you want to write, but do give it one last read and edit it when you’re in a better mood. When your mind is a bit clearer, you will interpret the emotions you went through a lot better. You might even figure out better ways to word things or cross out the lines you find unnecessary.

[Read: The honest secrets to let go of the past, be happy and look to the future]

4. Be honest

If you want the person to feel your emotions while reading your letter, write it from the heart. Everyone can spot a letter that’s not written from the heart. It’s extremely obvious, even to the untrained eye.

If you’re not crying or feeling emotional while writing the letter, the person who receives it won’t, either.

And don’t even think about stealing lines from a poem or a romantic novel just to be more dramatic. If the person knows you well enough, they can tell those are not your words. Just write the letter like you’re saying the words to the person as if they’re standing right in front of you.

[Read: 14 powerful ways to conquer unloving someone]

5. Keep it relatively short

You can write five pages if you want, but it’s more powerful if you can find a way to say everything you want in the least amount of words.

A letter should not pack a punch, not make them feel like they’re reading a novel. Don’t go into lengthy details, don’t overanalyze. Keep it straight to the point.

6. Don’t point blame

If you want your goodbye letter to make them cry, it’s not going to work if you spend a whole page blaming them for everything. No matter whose fault it was, it’s over. You gain nothing from blaming them.

The letter will be more powerful if you take the high road and not mention all of their mistakes. This is a goodbye letter, so just say goodbye.

7. Focus on you

You need to make the letter focus on you. How did they make you feel in the past? Why are you saying goodbye?

Even though you’re writing to them, this letter isn’t about them. They already know how they feel, now it’s your chance to tell them how you feel. When they read this goodbye letter and find out how devastated you are, they will start crying for sure.

[Read: 25 honest, self-reflection questions to recognize the real YOU inside]

8. Don’t be afraid to be vulnerable

A lot of us are afraid to seem weak, so we tend to suppress our emotions. There’s no point in doing that here. If you’re writing a letter, it means your feelings are strong and overflowing. You don’t have to be ashamed of having feelings!

The best way to write a goodbye letter that makes someone cry is to be vulnerable. Show them the real you. Don’t just say things that make you look “strong” and “cool” if that’s not how you actually feel inside. If they did something that really hurt you, or if you’re ashamed of what you did to them, let them know. [Read: What does it mean to be vulnerable? 15 ways you can open up more]

9. Don’t get stuck on the format

No one is born a writer. You shouldn’t stress out about the format of your article. It doesn’t need to rhyme or be a poem. You’re not freaking Sylvia Plath!

Write the letter however you wish.

[Read: How to deal with the pain of loving someone you can’t have]

10. The medium doesn’t matter

Whether you write them an actual letter, or type it and send it via email or as a text message, it doesn’t matter. A letter is a letter. You choose the medium in which you want them to receive it, one that you’re most comfortable with.

If you choose to send it online, they’ll always have a virtual copy of it. If you choose to write them a handwritten letter and hand it over, you run the risk of them losing it or spilling coffee on it, but it’ll have more value because it’s one of a kind. So choose whatever you prefer. [Read: The full guide to writing a heartfelt love letter like a true romantic]

11. Mention good memories

If you want your goodbye letter to make them cry, you should mention the positive memories you’ve had with them. Don’t just stick to the sad moments. The good memories always hurt the most.

When we’re trying to move on from an ex, it’s not the arguments and the breaking up that we think about. The laughing and kissing and the stories we shared will be the memories that haunt us. So talk about them if you want the person to become emotional.

12. Focus on details

When you’re writing a memory, focus on the details. Write it like how you’d tell a story. Write about how they touched you, what they said to you, the look in their eyes. These small details make a memory more vivid for the person reading it.

Take them back in time with you and show them what could’ve been. All the what-ifs will torment them as well.

13. State why you’re saying goodbye

They need to know why you’re saying goodbye. What happened? Why are you deciding to say goodbye now?

You need to answer these questions for them. If not, you’ll leave a space for misinterpretation. You need to be in control of your goodbye letter. [Read: How to let go of the might have been]

14. Say goodbye

At the end of the letter, make sure you say goodbye and send them good wishes. When someone writes you a goodbye letter but doesn’t end it, the chapter of your life isn’t fully closed.

If you want them back, then don’t close the chapter. If you want to move on, make sure they know this is a final goodbye.

[Read: 13 steps to find the closure you need to move on]

If you follow these tips, you’ll definitely succeed in making someone cry in your goodbye letter. Just remember to write from the heart and the rest will flow naturally.