Pretty Painful Grief Letters Review – The Book That Sits With You in Grief

I don’t usually write reviews, but this grief book deserves one.

It’s by the author of The Pretty Painful Grief Book (which I’ve written about before in detail). That first book is a workbook – it meets you where you are and says: here, process this, it helps. And it really does. I picked it up so many times when grief felt unbearable, and the prompts gave me something real and authentic to work through.

This new book, though, is different. It doesn’t ask anything of you. Instead it feels like a friend sitting beside you in silence, holding your hand while the wave crashes. It says: sit with this grief, you are not alone. It gives me a choice now when a grief wave hits – to process it, or to sit with it alongside someone who understands.

What’s Inside

Pretty Painful Grief Letters is a collection of letters, thoughts, and journal entries the author first shared on Instagram, later gathered into a beautiful book about life, death, grief, love, and everything in between.

It’s funny that Instagram is how I first found William Hunter Howell’s writing, because Instagram often tries to make everything aesthetic – even grief. And grief just isn’t. It’s messy. It’s crying on the floor at 2am. It’s getting angry at everything and anything (like I wrote about in my last post). It’s living with the ache of someone missing forever. Howell doesn’t pretend otherwise – his book is raw, real, and never dips into toxic positivity.

Healing too, as the book reminds us, isn’t about “moving on.” It’s about learning how to always feel a little bit sad, and finding ways to live with that sadness, and without the person you’re grieving for.

At the end of each chapter – and at the end of the book – there’s space to write your own thoughts. But I’d recommend getting both books: the workbook to process your grief, and this one to sit with it.

Why It Works For Me

What makes this book work is how easy it is to read. Grief, my eating disorder and recovery have wrecked my concentration, so I can’t manage long books. But this one is short writings, grouped into sections like lost, numb, broken, anger, guilt, alone, fear, love, heal. You can flip to whichever feeling you’re sitting in and find words that hold you there.

The workbook has become like a little first aid kit for grief. Now, with this book, I can choose: to process with prompts, or to sit silently with words that understand. It’s like adding another kind of medicine to the kit.

The first time I picked this book up, I wasn’t looking to process anything. I was just drowning. My chest was heavy, and all I wanted was for the ache to stop for a while. The letters didn’t fix it – they didn’t have to. They sat with me. And in that moment, it was enough to feel less alone in my sadness.

Howell’s writing is beautiful. I’d say “It’s like I wrote it myself” – but really it’s what I wish I could have verbalised about my grief and couldn’t. Which is often the problem with grief: there are no words, until someone else untangles the mess of emotions you’re feeling and writes them beautifully for you. This book makes you say “YES, THAT, EXACTLY” – a lot.

Grief is lonely. Despite the fact that nearly everyone has a grief story, no one talks about it. There are expected timelines, awkward silences, being made to feel like a burden if you mention your person again, and the same old platitudes: “But… they’re still with you.” Howell offers none of that. Just understanding, honesty, and company.

This book also feels, strangely, like talking to my best friend WeeGee. She hated toxic positivity too, and we bonded over hating the “absolute rubbish” the NHS spits out about recovery. She later told me they even peddle the same kind of “empty platitudes disguised as hope” in cancer treatment – things like “But you’re young, fit and healthy! You’ll be fine!” Only to be told later it was terminal. It shook her, because she felt like they were lying to her – and they were. Lies are not hope.

Her hope, even after hearing that, was: “I’m going to live what I can.” Given that she had an ED before, that was remarkable. People – especially now, in a world where everything online has to be “aesthetic” – often confuse realness with negativity or hopelessness. But WeeGee never was. Even in the face of cancer, she carried her own real, grounded hope.

That honesty and strength is exactly what these letters carry too – raw, no platitudes, just truth.

This wonderful book couldn’t have released at a better time for me. I’m in the part of recovery where every emotion comes back at full volume, and I often feel like I’m drowning. Sometimes there’s no energy left – after dealing with recovery, food, weight gain, and the grief of recovery itself – to process every single grief wave I have for my best friend. Sometimes I just need to ride it out, with this book and my Jellycat penguins beside me.

I wrote a lot about William’s first book because it gave me the tools I’d been searching for. This one doesn’t need as many words – because that’s the point. It doesn’t ask you to do anything. It just sits with you. And sometimes that’s all you need.

About William

You can find William’s grief story on Instagram in his own words. I also want to say that when I reached out to him, he was absolutely wonderful – he went above and beyond to answer a grief question I had. His books, his Instagram, and honestly just him as a person have helped me far more in my grief journey than grief therapy ever did.

I’ve written before about my experience with grief therapy on this blog, and since then I’ve been working hard on my own. William’s books have given me the tools to do that. And I have my recovery progress to show for it.

Grief Filled Final Thoughts

If grief feels lonely, this book makes it a little less so. And sometimes, that’s the best gift words can give.

You can find Pretty Painful Grief Letters on Amazon. This isn’t affiliated – I reached out to William because his words meant so much to me, but I chose to actually buy the book myself to support his work.

Everything I’ve written here is just my honest opinion. I wanted to write a review because these books are so underrated. They deserve to be the viral sensations on TikTok – not the toxic positivity “TikTok shop books” that look like they were printed on a home Epson and promise to heal everything in your life. (For the record: they didn’t even heal my grief over terrible printers).

I also wanted to write this post because if you’re reading this and are struggling with grief too, I want you to feel as supported as these books made me feel. I highly recommend them. They’ll tap in to your real grief emotions like sadness, emptiness and even rage, but also sit with you as you heal.

For WeeGee:-

3 thoughts on “Pretty Painful Grief Letters Review – The Book That Sits With You in Grief

  1. Karen's avatar Karen

    Thank you for sharing this resource. I’ve lead grief support groups on and off for over 20 years and am always looking for books to recommend. (I’ll be buying a copy for myself.) I echo what you say…grief is messy. And it’s unpredictable. You’ll be fine, fine, fine, then wham, not fine. Blessings to you on your grief journey. Karen

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