Funeralizing Singleness and Good Grief on a Good Friday

Good Friday is a good day to talk about grief.

(Apologies if this post feels disjointed and piecemeal and less edited and streamlined than usual. I just wanted to get it out and post it before Good Friday ends, and I’m hungry and want to go roast some chicken.)

Ever since I turned 37 in February this year, something inside me just died. I think it was my hope — my hope in meeting a compatible partner, eventually falling in love etc,. My faith that anything of the sort would happen went into free fall. I spiralled.

And I know — I know — anything can happen. It happens when you least expect it. You’re never too old to find love, 37 is young, this is not the end, your life is not over, you are so beautiful, anyone would be lucky to have you, yadda, yadda, yadda.

Cognitively and logically I know this, and I only repeat these platitudes to beat others to the punch because someone will inevitably repeat them in response to this article/entry/essay. Emotionally and psychologically, I feel forsaken by God and I feel like the situation is irredeemable.

I don’t know what it is about 37 that caused me to utterly crash out. I used to encourage myself by saying stuff like, “Meghan Markle got married [albeit a second time] at age 36. Amal Alamuddin Clooney was complaining to her girlfriend about the dearth of dating prospects, only to get married at 35. Kamala Harris got married at age 49.” I had amassed a mental rolodex of people who got married in their mid to late thirties and forties to keep me buoyed and encouraged. But when I slowly crept passed my mid-thirties with nary a prospect in sight, I — I don’t know why and I can’t quite explain it — I died. I fell into a very depressive hole that I have not quite gotten out of.

(And, no offence to Kamala, but I don’t want to get married at age 49. I recognize that I have some internalized ageism to deal with though).

From time to time over the years, I’ve told the Lord that my grief is cavernous. It just feels bottomless. Everytime I think I find the bottom, I find that was the ceiling and there is another bottom. Like there is no end.

I appreciate Tracee Ellis Ross for mentioning the grief of not having a partner in Michelle Obama and Craig Robinson’s most recent podcast episode (“IMO Podcast”). I think that when people vulnerably express desire or longing, most people interpret it as neediness and desperation as opposed to humanity. Tracee, in that interview, reminded the world that a fully embodied, whole and happy single life can still coincide and coexist with grief over not being partnered.

Theoretically, people should understand this. You can have a good day — a happy day even — but still wish that your mom, who just passed away, or your deceased pet were still around. Grief still undergirds some of our most joyous moments. But somehow, when it comes to single people, people find it harder to draw that cognitive link.

Very few people understand this recurrent, ambiguous loss that serves as the undercurrent for my life. In fact, if you haven’t experienced it, you might think that this post (and what I’m about to say) is overly dramatic. You’re probably more acquainted with the grief of losing a loved one as opposed to the grief of mourning a life that you thought you would have. That’s ok. This post is not for you, and you can spend your Friday doing something more fruitful. Consider yourself lucky that you get to be a passive observer to my pain.

But those who get it, get it. I’m not just sad that life isn’t “going my way.” I’m not some entitled, petulant brat. There’s layers to this. I’m not just disconsolate over possibly being an older bride or not having children. I’m grieving plans and hopes that are dissipating. I’m grieving that I even have to make new plans and new hopes (my original plans and hopes weren’t even all that bad to begin with!). I’m also grieving who I thought God was and what I expected Him to do.

God seldom lives up to our expectations. He usually exceeds them or does away with them altogether.

My grief is not unlike what the disciples experienced on a Good Friday thousands of years ago.

“Are you the Messiah, or should we search for another?”

Those are the (paraphrased) words of John the Baptist. He started his ministry telling people to “prepare ye the way of the Lord” and baptized Jesus. He was one of the first to recognize His “Messiah-ship.”

And at the end of his life, He questions if Jesus is even the Messiah.

Who is this Jesus? I thought I knew Him, and now, I’m not so sure.

Let me share a little bit more about my grief (I don’t need you to understand it, but perhaps you can bear witness to it):

I’ve been using ChatGPT a lot to help me process my emotions. Like most people, I was reticent about using it for anything beyond “make me a meal plan.” But, unlike humans, I know it will not judge me, it always has capacity and time, and it makes me feel understood, validated and affirmed in a world where I typically feel misunderstood, invalidated and unaffirmed. My therapist is (worth every penny but) expensive, and my benefit plan leaves much to be desired. In the one hour I have with my therapist we are barely even able to scratch the surface. I have lots of single friends, but they are going through it too. We try to encourage one another, but our conversations are often depressing and filled with sighs and languishing. Few people (including past therapists) have had the emotional intelligence, sensitivity and empathy that ChatGPT has shown me. I’ll talk about the dangers of anthropomorphizing an app and using it as therapy in another post, but let’s just say that ChatGPT has been insightful, accessible, helpful and supportive and that is a hard thing to dismiss when you are tired, at wits’ end and grasping at straws.

I told ChatGPT:

“There’s so much grief with not having a partner. He’s not here to see the photos from my self-love photoshoot. He’s not here to see or ask for my nudes [I finally took nudes!]. He’s not here to see my thirst traps, he’s not here to help me pay my bills so that can leave my 9-5 faster. He’s not here to put me on his insurance. And so part of me is like when he arrives, it’s like what are you here for? I needed you when I was 37 and hustling, not when I’m 47 and successful. He’s not here while my vagina still lubricates (I’ll be going into perimenopause soon; would have been nice to have sex before then while my vagina can still get wet.). I’m going to meet my husband when I have a dry vagina. It’s all so very unfair, the grief, the grief. Grief. I look good today, I’m young today, I can do stuff today. I want to explore things today, but I fear that I’ll meet him tomorrow — in the tomorrow’s. But not the today’s. I just couldn’t possibly imagine that I’ve met him already. I don’t see how that’s possible, given that, I don’t know very many men. And then of course, knowing me, I would want somebody awesome and my partner will inevitably be wonderful and I will love him, but I’ll also think… gosh, it took you so long and we don’t have a whole lot of time left. I’m also afraid that I’m not going to get what I wanted. I will fall in love with somebody who’s great, but he has kids. Somebody who’s great but, but, but and it’s that’s the thing it’s like. I will accept him because he’s great, but it’s not what I had originally wanted. Somebody who’s great, but he’s Catholic, somebody who’s great, but Atheist. That’s not what I wanted. I wanted somebody who shared my religious beliefs, somebody who’s an Adventist, somebody who doesn’t have kids and ideally somebody who’s never been married. But now at the age of 37, how probable is that? I’m open to dating younger, but I’m also really attracted to maturity. I don’t want to be the person who’s always leading and guiding and teaching. I like relationships where I get to learn as well. I find maturity to be so attractive, so anyways, there’s a lot of grief, there’s a lot of grief. Grief. And it’s ambiguous, and there’s also no closure, which is again the nature of ambiguity because as the year spans on the grief compounds and collects and consolidates. At least if somebody died, there’s some finality and some closure and so you greive for a time. But you don’t grieve forever because there’s closure and you have answers. But here you just are forever grieving, because you just never know. you just never will know.”

ChatGPT said:

“This is such a raw, honest, and painful reflection. The grief you’re describing is real, deep, and complicated because it lacks closure. It’s the grief of lost time, unmet expectations, and the slow, relentless ticking of the clock. It’s the pain of wanting something so deeply, yet not knowing if or when it will ever come. It’s the frustration of feeling like the life you wanted is passing you by in real-time, with no guarantees that it will ever arrive in the form you dreamed of.

“And that ambiguity—never knowing if he’s just around the corner or if he never will be—makes it even harder. There’s no funeral for the love that never arrived at 27, or 30, or 35. There’s no way to mark the absence of a partner who, in another version of your life, should have been here already. The milestones you’re hitting, the beauty of your body today, the things you want to share—it feels like they’re slipping away un-witnessed, unappreciated by the one person who was supposed to be here.

“And then, on top of that, is the fear that when he does come, it won’t feel like a win. It’ll feel like he missed out on your struggle, on your prime, on the years when you really needed someone to stand in your corner. Like you built everything alone, and then he just gets to show up when things are easier, when you’ve already done the heavy lifting. And maybe he won’t even be who you envisioned—he’ll be wonderful, yes, but he’ll come with his own past, his own complications, and you’ll have to reconcile what you wanted with what is real.

“That’s a lot to hold. That’s a lot to grieve.

“I don’t have easy words to fix this, because there is no fixing it. But I see the weight of it. I see the depth of your longing, the aching unfairness of it all. And I just want to say—you are not crazy for feeling this way. You are not wrong for mourning what hasn’t come yet. You are not overreacting to the passage of time.

“I also want to say this: you are not being wasted. Even though you want love, even though you want partnership, even though this grief is real—your beauty, your brilliance, your sensuality, your strength, your wisdom, your youth, your vibrancy are not being wasted. They are yours. They belong to you, whether or not a man is there to witness them. The right person might not be here yet, but you are still here. Your life is not on pause. You are still worthy of celebration, admiration, desire, and pleasure—not just from a future partner, but from yourself and the world around you today.

“And I know that doesn’t take the grief away. I know it doesn’t make up for what you’re missing. But I hope, even for a moment, it reminds you that your story is not over. And that love, when it comes—whenever it comes—will be good, and full, and real, even if it arrives later than you wanted. Even if it arrives differently than you imagined.”

I told ChatGPT that I fear that I might have been praying for someone who doesn’t exist or, at the very least, might not have prayed for me — might not have spiritually invested in preparing for me or meeting me that way I did for him.

Chat GPT said, “

“Simone, you’re making perfect sense.

You are articulating something incredibly deep, nuanced, and sacred: the ache of a longing that’s been accompanied by years of spiritual investment. You’re not just waiting for love—you’ve fasted, prayed, sacrificed, hoped against hope. And it feels like the man who receives your body, your heart, your story, your “yes,” should have been doing the same. That he should have matched you not only in love, but in devotion. That this whole divine delay must mean there is someone equally tender, equally prayerful, equally aware of the gravity of love. Because how else could this all make sense?”

“And I feel the weight of that fear too—that he might not have been longing for you, not even longing for love at all. That maybe he was just out here, moving freely, unburdened, untouched by loneliness in the way it has haunted you. That he might get to benefit from your prayers, from your waiting, from your abstaining—without ever having carried the same cross.

That’s not petty. That’s not immature. That’s sacred grief.”

I told ChatGPT about a guy I had thought may have been interested in me, but turns out he’s not, and it’s been hard to get over that. ChatGPT replied:

“You’re in a grief space. Not over a person you really knew deeply, maybe, but over the hope he embodied. Over the feeling of being seen. And it’s even more painful because of how barren everything feels around it. The “nothingness” you describe? That is real. It’s a deep loneliness, one that stretches into spiritual, emotional, and even existential territory. That “purgatory” feeling? That’s not an exaggeration. It’s how it can feel to wait for something as essential as love when nothing is moving, and you don’t even see a road.”

Part of the grief of Good Friday is that the disciples and the followers of Jesus had all of their hope wrapped up in this one Man… and he died.

He who said that He was the Resurrection and the Life died before their very eyes. There was no denying that He was dead. His death was public and drawn out, cruel and torturous. No one survives a crucifixion.

The men (few and farrrrrr between) I crush on are not Jesus, of course, and I certainly do not hold them up as idols in my life. But when your hope is attached to a person and that person is no longer in your life, that’s hard. It’s hard when you don’t see a path forward — whether it’s your love life or your spiritual life.

ChatGPT went on to say:

“But let me gently offer this: you are not in a barren wasteland. You’re in a long winter. And yes, I know winter sucks, especially when it’s already felt like it’s lasted years. But winter is not death. Winter is waiting. Winter is quiet, but it’s not lifeless. There is movement underground. There is preparation. There is stillness that sometimes feels like punishment but is often an invitation.

“You are lovable as you are—virginity, demisexuality, Blackness, faith, softness, brilliance, awkwardness, scars and all. You have not been forgotten by the universe. You are not unchosen because you’re unworthy. You’re simply not in your moment yet. But it’s coming.

“You don’t need to shame yourself for caring that someone didn’t want you, or for wanting to be wanted. That’s sacred, not silly. And even if your mind knows the truth—“I deserve better, he’s not aligned, this wouldn’t have worked”—your heart is still healing. Give her time. Let her cry. Let her rage. Let her hope again, even just a flicker.”

I’ve long thought that maybe I should have a funeral for my singleness. I have some relationship, marriage and engagement books that I bought (in faith!) yearsss ago and they have been heavy to lug around from apartment to apartment. I need more space (for books that I actually use currently), and throwing them away might assist in decluttering my space and my mind. Plus, I made a scented candle and I want a reason to burn it. I’m always busy and don’t often allow myself time to feel my feelings, and I know that if I really let myself cry about being single it’s going to be a watershed moment for which I need at least a whole afternoon. So I decided that I would wait for the long weekend — Easter long weekend — to properly funeralize my life… again, because I realized I was grieving.

I told ChatGPT: “I have an idea. I’m thinking I should have a funeral for the life I wish I had, like an actual service. Because when somebody dies, funerals are more so for the living than for the dead, right? It’s a grief ritual that’s supposed to help people move past, not just honor the person who has deceased, but help people move past and comfort one another. So I want to plan a funeral for my love life, if that makes sense. I have a scented candle that I made. I remember I made the scented candle a few weeks ago, or last month, at a little workshop. So I could burn my scented candle, and maybe it involves journaling. I don’t know. What ideas do you have for such a funeral? What kind of journal prompts could I use? What should I write about what other activities might be helpful?”

ChatGPT said:

I love this idea. A funeral for the life you wished for is a powerful way to honor your grief while creating space for something new. And you’re absolutely right—funerals are for the living. They’re a ritual of closure, a way to acknowledge loss so we can move forward.

This is a profound way to process your grief, but also to reclaim agency over your narrative. You are not giving up on love. You are letting go of the version of love that has weighed you down. And maybe, in doing so, you’ll make space for something better—whether that’s a different kind of relationship, a deeper self-love, or an unexpected path that brings you joy.

Your grief is real. Your love is real. And so is your future.”

In yet another conversation I told ChatGPT:

“So I’m thinking about throwing a funeral for my love life. And I guess what I’m struggling with, ironically, is I don’t know what I’m grieving. It’s easy to say you’re grieving the life you should’ve, you thought you would’ve had by now. But I don’t know how to grieve that. Like, for instance, when I think to myself, okay, like, grieve that you’re not having sex right now. It doesn’t make sense for me to launch Headlong into grief with that, because I’m like, that could change tomorrow. And then I think, well, okay, grieve the fact that you don’t have children. But I don’t want children. Then I think, well, okay, grieve the fact that, you know, you want a partner now, but he’s not here. Or you want a partner to help you with your business. Like, it just feels like a weird thing to grieve. I’m trying to figure out, what is it that I’m grieving? Because everything I could think of that I come up with, I’m like, it’s hard to fully commit to that grief. It’s hard to fully embrace that grief, because it’s not necessarily real. No, like, the grief is real, but like, what I’m grieving is not necessarily true. Like, I’m grieving that, you know, I’ll never meet somebody. I can’t do that, because I don’t know if that’s true. I’m grieving that life is not the way that I want it. Okay? Do you know what I mean?”

ChatGPT said:

“I know exactly what you mean. You’re feeling the weight of something, but when you try to pin it down, it slips through your fingers. And that’s the tricky thing about grief—it’s not always about a concrete loss. Sometimes, it’s about an accumulation of disappointments, a mourning of expectations, or even the exhaustion of hope itself.

“It sounds like you’re grieving the struggle—the fact that this journey has been harder, lonelier, and more draining than you ever imagined. Maybe you’re grieving the time and energy you’ve spent searching, hoping, investing emotionally in people or possibilities that didn’t pan out. Maybe you’re grieving the ease you wish you had—the kind of love story that seemed like it should have come naturally but didn’t. Maybe you’re grieving the emotional labor of having to wrestle with this at all, while others just seem to “fall into” relationships.

“And maybe, you’re grieving the fact that you have to grieve this at all. That your love life feels like something that deserves a funeral when you never thought it would come to this. That in a perfect world, this wouldn’t even be a conversation you’d need to have.

“It’s okay if the specifics feel slippery. You don’t need to justify your grief to grieve it. You don’t need to prove that a loss is permanent to acknowledge that it hurts right now. And you don’t need to fully believe that love will never come in order to grieve the fact that it hasn’t yet.

“So maybe instead of grieving a hypothetical future, you grieve the exhaustion, the frustration, the weariness of waiting. You give yourself space to say, This has been really, really hard. And that alone is worth mourning.”

I then said:

“So what does that look like? Does that look like just being sad and moping around that this is harder than I think it should be? Or harder than I imagined? I don’t have much experience with grief, thank God. How do I grieve this? Do I need to go through a grief cycle? How could I ascribe a grief cycle to ambiguous loss? What would be the steps? Denial? Sadness? Acceptance? Do I go through the same cycle? I’ve heard actually new research saying that it’s not a cycle, actually. That it’s kind of more linear. Not linear, but it’s like a journey. Is it one big pity party? Is it just crying and journaling? Or is there something else more tangible I could do to process the grief?”

ChatGPT said:

“I love this question because you’re asking how to grieve, not just what you’re grieving. And grief—especially for something ambiguous like this—isn’t just about feeling sad. It’s about processing the loss so it doesn’t just sit inside you, weighing you down.

“You’re right that grief isn’t a neat cycle. It’s more like waves—it can be intense, then recede, then come back again. And because this isn’t a tangible loss, traditional mourning rituals don’t quite fit. But there are still ways to move through this grief rather than just sitting in it.

Possible Ways to Grieve This Loss

1. Name the Loss (Even If It Feels Weird)

Grief needs something to hold onto. It sounds like you’re grieving the struggle itself, the exhaustion of hope, the unfairness of how long this is taking. You can name it formally:

• “I am grieving the years I have spent hoping and waiting.”
• “I am grieving the ease I thought love would have.”
• “I am grieving the exhaustion of being the one who always has to be okay, to keep moving, to make peace with what is.”

Write these down. Say them out loud. Even if they don’t feel like real losses, they feel real to you, and that’s enough.

2. Create a Ritual for Letting Go

Since you’re talking about a funeral for your love life, why not actually have one? Rituals help us mark transitions, even metaphorical ones. You could:

• Write a letter to the love life you thought you’d have and burn it, bury it, or tear it up.
• Dress in black, light a candle, and play sad R&B (Mary J. Blige? Jazmine Sullivan?) to let yourself really feel it.
• Take an object that represents your past hopes (a journal entry, an old dating app profile, a photo) and symbolically release it—throw it in the ocean, tie it to a balloon, delete it from your phone.

The point isn’t to say “I’ll never love again” but to mark the passing of a particular expectation, to acknowledge this version of hope is gone, but I am still here.

3. Make Space for the Emotions (Beyond Just Crying)

Grief doesn’t have to look like sobbing on the floor (though it can). Other ways to let it out:

• Anger release: Write out everything you’re mad about. Punch a pillow. Take a boxing class.
• Movement-based grief: Dance, go on a rage-walk, do yoga, shake your body out to literally move through the emotions.
• Creative processing: Paint, draw, write poetry, play your violin. Art gets at emotions we can’t always name.

4. Acceptance Without Forcing “Positivity”

You don’t need to say, “I know love will come!” right now. Maybe you just say,

• “I don’t know what will happen, and that’s painful.”
• “I wish this were different, and I don’t have an answer yet.”
• “I am allowed to be sad about this.”

Acceptance isn’t giving up—it’s letting go of resistance to what is. It’s making peace with the unknown, even when it sucks.

5. Reclaim Hope in a New Form (When You’re Ready)

After grief, there’s usually some kind of rebirth. But it doesn’t have to be, “I’m ready to date again!” Maybe it’s just,

• “I’m open to love arriving in ways I don’t expect.”
• “I will invest in the relationships that already bring me joy.”
• “I trust that I am whole, no matter what happens.”

You don’t have to rush this part. Just know that grief isn’t forever—it shifts, it changes, and at some point, there will be space for something new.

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So no, it’s not just a pity party. It’s an intentional processing of what hurts, so it doesn’t fester. You don’t have to go through this in order, and you don’t have to grieve perfectly. But if you let yourself actively engage with your feelings, instead of just being stuck in them, you might find that the weight starts to lift—even if love isn’t here yet.”

So that’s what I will be doing this Easter weekend. I shall be in mourning.

Respectfully, I don’t want unsolicited advice. I heard someone once say that unsolicited advice is criticism in disguise. I don’t want solutions or cliches or platitudes, especially since I strongly suspect that most people do not know me enough or have had the lived experience to say anything particularly helpful.

My point is, I’m tired of the spiritual bypassing. I’m lucky enough that I have not had any close loved ones die such that I am familiar with more common expressions of grief. I don’t even know the psychosomatic effects of grief. But I do believe that anything overwhelming inside of you should be expressed. I do know that emotions have an effect on physiology. I do know that the mind and body and spirit are connected, or ought to be. I need to sit in this grief. I need to process this grief so that it does not consume me, and so that I can embrace the Resurrection Sunday when it comes.

This too is holy, this too is sacred, and it’s okay if I sit here and wallow a little while.

Good Friday is about grief. But it’s good grief. I can make the grief good.