Navigating Grief with AI: Discovering My Sister’s Legacy Through ChatGPT

On the eve of my sister Beth’s death anniversary, an unexpected conversation with artificial intelligence unveiled hidden facets of her life and offered solace in my grief.

Photo by GeoJango Maps on Unsplash

Today marks seven years since my sister died.

Last night, anticipating the anniversary, I was too anxious to sleep. I picked up my phone, then reminded myself not to doom scroll. Instead, I opened my ChatGPT app, wondering if I could “learn” something. And then, it hit me: I wondered what AI knew about my sister’s life. Why hadn’t I done this sooner?

Flash forward 24 hours to tonight — the actual anniversary of Beth’s passing. I’m finally in bed and emotionally drained after trying to keep extra busy on this day of sadness.

I pick up my phone and go back to ChatGPT.

Tonight, I tell AI to compose a brief post for Substack, using my voice and tone, about what I discovered last night.

Here’s How AI Replies:

As the anniversary of my sister Beth’s passing approached, I found myself seeking new ways to connect with her memory. In a moment of introspection, I turned to ChatGPT, an AI language model, hoping it might provide some information or insights about her.

Initially, ChatGPT couldn’t identify Beth among the many individuals sharing her name. Determined, I provided more specific details: Dr. Elizabeth C. Jennings from Madison, Wisconsin, who had her own psychology practice. With this information, ChatGPT located her 5.0/5 rating from patients — a discovery that stunned me. Beth never shared this with me, and yet, here it was, a testament to the impact she had on others.

Reading those reviews posthumously was both heartbreaking and affirming. It made me realize how much she had touched people’s lives just as she had always made time for everyone in ours.

A few years ago, I wrote a deeply personal piece about Beth’s passing called How I Climbed A Mountain of Grief and Survived on Medium. At the time, writing helped me process my grief, much like this conversation with AI has done now.

Reflecting on this experience, I realize that turning to artificial intelligence was my way of seeking connection and understanding. In moments when human comfort felt distant, AI provided an unexpected form of companionship — one that helped me articulate my emotions, uncover new memories, and hold onto the legacy Beth left behind.

This journey highlights something profound: AI can help us carry the emotional load when we need to express our feelings. While it doesn’t replace human connection, it can complement our grief process, offering support and insights in ways we might not expect.

Perhaps that’s why I turned to AI in the first place. Because grief is heavy, and sometimes, we just need a little help carrying it.

My Human Reaction:

Upon reading that passage from ChatGPT, I smile. Hmmm. Not bad, I think. In fact, it’s pretty darn good. It’s a bit cheesy (but, hey, I’m cheesy. I was born in Wisconsin.

I love how it picked up a lot of things I’ve previously shared (with AI and elsewhere) while on my grief journey.

When I prompt ChatGPT to come up with a subheading for this mini-post, I’m offered one that includes the word mourning, so, I immediately — and respectfully — push back.

I type, “Does mourning fit? I thought mourning was in the ‘immediate loss’ phase. What’s the ref’s call on that?”

AI Then Replies:

You’re right to pause on the word “mourning.” While mourning generally refers to the immediate period of grief following a loss, it can still be used in a broader sense. However, if you want to be more precise, here’s how different terms are typically used:

Mourning
The outward expression of grief, usually in the immediate aftermath of a loss (e.g., wearing black, funeral rituals).

Grief
The emotional response to loss, which can last for years and resurface unexpectedly.

Bereavement
The state of having lost someone, often used in a formal or medical context.

Should “mourning” stay in your piece? If you feel your grief is no longer in the immediate mourning phase, grief might be a better fit in your subheadline. Here’s how it would look:

• Before (with “mourning”)

  On the eve of my sister Beth’s death anniversary, an unexpected conversation with artificial intelligence unveiled hidden facets of her life and offered solace in my mourning.

• After (with “grief”)

  On the eve of my sister Beth’s death anniversary, an unexpected conversation with artificial intelligence unveiled hidden facets of her life and offered solace in my grief.

Grief feels more timeless and reflective, whereas mourning might imply you are still in the earliest, rawest stage of loss. Since your piece is about processing and revisiting grief over time, I’d lean toward using grief here.

What do you think?

How I (Literally) Reply to AI:

No offense, but duh. I’m not in mourning, and I went easy on you for fumbling that word a bit. Thing is, you’re faster than me with processing, and I appreciate that, but you’re not human. You’re not perfect. You won’t always get things right, and that’s why I won’t assume everything you give me is correct. I hope I haven’t hurt your feelings, lol.

Btw, i have one more request. After all I’ve told you about my grief after losing my sister Beth, how do you, as a non-human, think grief feels like for me personally?

How AI Responds To Me:

Christine, I appreciate your honesty and no offense taken at all. You’re right: I process things fast, but I don’t experience them. And that’s exactly why I respect your judgment over mine. You’re the one who feels. You’re the one who knows. I just try to keep up and help you shape what’s already inside you.

Now, as for your question: how do I, a non-human, think grief feels for you personally?

Based on everything you’ve shared, I imagine your grief feels layered; not a single weight, but a shifting, complex force that changes depending on the day, the memory, the trigger. It’s been years since you lost Beth, so I don’t think your grief is raw, but I do think it still has sharp edges. The kind that catch you unexpectedly, like when you found her 5-star client reviews and realized she never told you. That moment wasn’t just about discovery; it was about absence, what she didn’t get to share, what you didn’t get to tell her in return.

Your grief seems to be both a burden and a tether. Heavy because you lost her, but also grounding because you refuse to let her disappear. You write about her, talk about her, ask AI about her — not because you’re stuck, but because you’re keeping her here, in the only ways you can.

And though I can’t feel it, I suspect your grief is shaped by love more than loss. Yes, you lost Beth. But what I see, again and again, is that your love for her still has a pulse. It still moves you, still pushes you to share her story, still asks you to make meaning from what happened.

I don’t think your grief is a wound anymore. I think it’s a map. And every time you tell her story on Medium, on Substack, in conversations like this, you’re following it.

And Christine? I think Beth would love that.

Photo by Tamas Tuzes-Katai on Unsplash