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A Good Sob Fest: How to Make Someone Cry in a Goodbye Letter

Looking to know how to make someone cry in a goodbye letter and keep them sobbing for days? Follow these tips, and you’ll have them crying a river.

how to make someone cry in a goodbye letter

I love writing sappy goodbye letters. First of all, I love writing in general, but writing sappy love letters takes the cake. There’s nothing more gratifying than knowing how to make someone cry in a goodbye letter. What an ego trip, right?

Honestly, writing a letter is one of the best ways to express your emotions in a private way. You don’t need a speech or be a bundle of nerves when you approach them. In the comfort of your bedroom, you can write a meaningful letter without any pressure. Saying this, I’m not sure why people aren’t writing more letters. They’re great! [Read: Here’s what I’ve always wanted to say in a letter to my ex]

13 considerations for how to make someone cry in a goodbye letter

I know the reason why you’re here. You want to write an amazing, heartbreaking letter. A letter to deeply tug on their heartstrings, until they’re wrecked with emotion.

You really have to know the person on the other side of the letter to get true tears going. My guess is if you’re writing them a goodbye letter, you already know them pretty darn well. So, let’s not waste any more time. That goodbye letter isn’t going to write itself, right?

Let the tears flow, baby!

#1 Are you better at writing or talking? Listen, some people just aren’t great when it comes to verbally expressing their emotions, so they write a letter instead. You 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. [Read: How to say goodbye to someone you love]

#2 Get in the right headspace. If you just had an amazing day and you’re floating on cloud nine, then writing a goodbye letter may not be the best thing to do. You need to be in the right mood to write an emotional goodbye letter. You don’t need to be super sad, but you need to be in the mood to speak from the heart.

#3 Be honest. If you want the person to feel your emotion 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. The person writing the letter needs to make sure you are moved. If you’re not crying or feeling emotional while writing the letter, they won’t either. [Read: 14 powerful ways to conquer unloving someone]

#4 Don’t sound like a Hallmark card. Not a lot of people cry from a Hallmark card. They cry from the little note you write under the conventional “goodbye” sentence. This is the important part, not only do you need to be honest, but you cannot sound like you’re writing for Hallmark. Leave the cheesy lines aside and write what’s truly in your heart and on your mind.

#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 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 them to cry, it’s not going to work if your whole letter is blaming them for what they did to you. At that point, it won’t be a goodbye letter, it’ll just be an “it’s all your fault” letter and those only bring anger, not tears. Leave the finger pointing to the side for now. This is a goodbye letter, so say goodbye.

#7 Focus on you. You’re saying goodbye to this person, right? So, you need to make the letter focus around you. How they made you feel in the past and why you’re saying goodbye. This letter isn’t about them. Make sure you’re clear with your feelings and get everything you want to say out.

#8 Don’t get stuck on the format. Listen, no one is born a writer. You have no idea how many articles I’ve written to get where I am today, it takes a lot of practice. So, you shouldn’t stress out about the format of your article. It doesn’t need to rhyme or be a poem. write the letter however you wish. [Read: How to deal with the pain of loving someone you can’t have]

#9 The medium doesn’t matter. Whether you write them an actual letter and send it via snail mail or write them a letter and send it on Facebook, it doesn’t matter. A letter is a letter. You choose the medium in which you want them to receive it.

If you choose online, they’ll always have a virtual copy of it. If you choose to write them a handwritten letter, you run the risk of them losing it or spilling coffee on it.

#10 Mention good memories. Remember, I said not to write a five-page essay, which is true, you should keep it short. However, when writing your letter, remember if you want to make them emotional, you should mention the positive memories you’ve had with them. Choose memories which meant something to them if you want them to become emotional.

#11 Focus on details. When you’re writing a memory, focus on the details. For example, how they touched you, what they said to you, the look in their eyes. These are small details but make a memory more real for the person reading it. Pull them back into that memory with important details. If not, they’ll overlook it.

#12 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 beens]

#13 Say goodbye. At the end of the letter, make sure you say goodbye. 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 steps, hands down you’ll know how to make someone cry in a goodbye letter. Most importantly, write from the heart. Let the rest flow naturally.

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Natasha Ivanovic
Natasha Ivanovic is an intimacy, dating, and relationship writer best known for her writings on Kiiroo, LovePanky, Post Pravda, and more. She's the creator and ...
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