Shoulda, Coulda, Woulda: A Widow’s Take on Hindsight, Heartache, and Our Imperfectly Perfect Life

The Hindsight Loop

If there’s one thing widowhood has gifted me—besides the crippling loneliness and the fun privilege of making every single decision for the house, the dogs, and the budget solo—it’s an internal monologue that is obsessed with rewriting history. Welcome to the "Shoulda, Coulda, Woulda" cycle. It’s my brain’s favorite pastime: a high-definition, 24/7 loop of all the ways I could have been a better wife, a better helper, or just a better "mind reader" when Greg was still here.

I’m suddenly convinced that if I had just stood in the yard for five extra minutes while he was working, the entire trajectory of our marriage would have been upgraded to "Perfectly Aligned Power Couple."

Spoiler alert: It wouldn't have.

I’m learning, slowly, that forgiveness is not just about what we owe to others; it’s about what we owe to ourselves. As Oprah once said,

"True forgiveness is when you stop wishing things were different."

That is the hardest work I have ever done—letting go of the wish that I could have been someone else, or that he could have been someone else, and finally accepting that the life we built was the only one we were ever meant to have.

The Curator and the Creator

People love to say "opposites attract," but they usually forget that after 32 years together—and 30 years of marriage—those opposites can make you feel like you’re speaking different languages. I’m the curator. I’m obsessed with aesthetics, I love throwing parties, decorating, and I’m always the one with the camera, trying to preserve the magic of a moment.

Then there was Greg.

He didn't care about the aesthetic; he cared about the utility. His fashion sense was "I found this in a pile of sawdust"—specifically those white t-shirts he insisted on turning into sleeveless disasters. If I hadn't stepped in as his unofficial Fashion Police, he might have tried to wear those t-shirt rags to a black-tie event—and he probably would have pulled it off, too, just by the sheer force of his own stubbornness. But beneath those atrocious shirts was a man married to his work. He had an incredible gift for taking wood scraps—trash to everyone else—and turning them into something beautiful and meaningful.

The Chasm and the Reset Button

When it came to physical affection, people might have called us "oil and water." I was constantly looking for the hug, the hand-holding, the cuddling on the couch, the "I’m here," and he was out in the garage, hunched over some intricate wood creation or sharpening lawnmower blades. For a long time, I viewed that as a fundamental incompatibility. But lately, I’ve been thinking about the chemistry of it—oil doesn't fight water; it rests on top of it, creating a new, layered surface.

Maybe we weren't meant to mix.

Maybe the "oil" of his quiet, focused creation and the "water" of my need for connection weren't opposites to be reconciled, but layers that made us a complete, stable whole. I was the curator—the one who focused on the life happening inside the house, while he was the creator—the one who spent his energy making sure the house had a foundation, a workbench, and beauty born from scraps.

He wasn't just "busy." He had this incredible gift for taking wood scraps—the stuff everyone else saw as trash—and turning them into something beautiful, useful, and deeply meaningful.

We even talked for years about building him a proper, separate workshop, but instead, our garage became his makeshift sanctuary. My car spent decades serving as his secondary workbench, consistently covered in a fine layer of sawdust, even though he kindly moved it to the driveway in an attempt to avoid it. I regret that we didn't just bite the bullet and build him that shop. I spent so much time worrying about the logistics, never realizing that for Greg, the workshop wasn't just a building—it was his way of creating beauty for the people he cared about.

Greg had a way of showing love that didn’t always need words; it needed wood, a bit of stain, and time. He built a small, handmade box for our daughter, Avery, carving his pet name for her—‘Chicky’—into the inside of the lid. For years, it held her treasures. Years later, that same box held the seeds of remembrance we shared with our family and friends at his celebration of life. It’s a profound irony that the very thing he created to hold her small, childhood joys ended up holding the promise of new growth for all of us as we said goodbye.

It was his final, quiet way of tending to us, even when he could no longer be there to build the next thing.

And if I’m being truly, brutally honest—which is apparently what happens when the filter comes off after you lose your person—I was occasionally, quietly jealous of that focus. I watched him pour himself into his woodworking projects, turning strangers into friends and scraps into art, and I found myself thinking, 'I love that you do this for them, but when do I get to be the one you’re this invested in?' I felt like I was competing for a limited resource of "Greg-energy," and I often felt like I was losing to a garage full of projects or a work client’s urgent request.

We were two people constantly misreading each other’s signals, which inevitably created a sort of chasm between us. But, if I’m being honest, it wasn't a total disaster. While we were often at odds over how to handle mundane things like PDA or the sheer amount of sawdust on the garage floor and walls, we always had our own secret language of passion to fall back on.

When the "I don't get you" gap felt too wide, we had a way of finding our footing that didn't require a single word. Let’s just say that whatever lack of hand-holding we had in public, we more than made up for behind closed doors. It was our ultimate reset button—the one place where the "Odd Couple" dynamic stopped clashing and actually started working in our favor. It was the fire that kept us warm, even when we were busy being entirely too stubborn to admit we were on the same side.

Now, in the quiet of this new life, that "secret language" feels like a double-edged sword. It’s a beautiful memory to hold, but it also casts a long, intimidating shadow. How do you even entertain the idea of letting someone new into your life when you know exactly how high that bar was set? That level of physical chemistry—that unique, silent frequency we hummed on—is so rare that it feels almost impossible to imagine ever finding it again with another human. It makes the idea of "moving forward" feel like a betrayal of the magic we had, or worse, a setup for inevitable disappointment. I find myself wondering: Was that my one shot at that kind of connection? And if the answer is yes, how do I build a future that feels whole without it?

The Autopilot Trap

We fell into the "autopilot trap." We treated our marriage like a high-performance vehicle we assumed would keep running on fumes. We were so busy being "Mom-ager Jen" and "Hard-Working Greg"—tackling the careers, managing the kids, keeping the wheels on the bus—that we rarely stopped to check the oil.

We were JUST reaching midlife, finally starting to relax and enjoy what we had worked for, getting along better than ever,

and then…

The clock just stopped.

I spent too much time wishing Greg was someone he wasn't. I fell in love with HIM—the real, stubborn, t-shirt-shredding, huntin’ and fishin’, work-obsessed country boy—not a version of him I could edit to fit my "perfect partner" checklist.

We let our general maintenance slide, too. We got so caught up in the rhythm of our own separate lives that we stopped prioritizing the "us" stuff. I wish we had been more intentional about date nights, or even just finding that new hobby to share together, instead of just collapsing on the couch to binge another Netflix series. I spent so much time worrying about the future or fixing the present that I forgot to just be with him.

Looking at this photo, I’m reminded of how well we actually could work together when we had a shared mission. Installing the downstairs wood flooring was one of those rare times we found our own rhythm—messy, but unified. I spent so much time worrying about the future or fixing the present that I forgot to just be with him in these moments of collaboration.

And then there was his voice. He had this thick, Southern drawl—the one that made no sense given he was raised in Southern Illinois, but sounded like he’d stepped straight off a porch in Tennessee. He had a way of saying my name, drawling it out as “Gee-yun” instead of "Jen," that was so incredibly sweet and endearing.

It was the soundtrack to our life, and oh, how I wish I could hear him say it... just one more time.

I realize now I was trying to "optimize" a relationship that was already exactly what it needed to be. Accepting that—and letting go of the unrealistic expectations I held—is perhaps the best way to honor the relationship we actually had, rather than the one I kept trying to rewrite in my head.

Classic "us"...me showing affection & him resisting!

The Gift of Presence

Piero Ferrucci once said,

"To be in the present with someone else is a gift. The gift of attention is perhaps the most precious and envied of all, even though we do not always realize it."

It’s a beautiful truth that I’ve only recently come to appreciate. When I think back, if I had a "rewind" button, I wouldn’t change the big stuff. I wouldn’t try to fix our schedules or force different hobbies. I’d just hit pause, put down the phone, walk into the garage, and sit on a bucket near him while he worked. I wouldn’t need to "help," "optimize," or "supervise" the project.

I’d just exist there with him.

I’ve learned the hard way that we spend so much of our lives waiting for the "right" time to be fully present—waiting for the project to be done, the house to be clean, or the weekend to arrive. We treat presence as a luxury we’ll afford once we’ve finished our to-do lists.

But the bucket wasn't just a place to sit;

It was a front-row seat to the life we were actually living.

The weight of the last two years has left me feeling like I’m constantly wading through a fog. Between April 2024 and February 2026, I said goodbye to Greg's dad, Tom; our best friend, Stacey; my Daddy; Greg's sister, LaNell; Greg; and our best friend, Tiffany. When you lose that many people you love in such a short window, your brain stops trusting the present moment—it becomes a survival mechanism to simply drift away, to live anywhere but here.

​But I am realizing that while drifting is a natural response to grief, it’s also a thief. It steals the moments I do have with the people still standing right in front of me. Just last night, I was watching a movie with Avery, and for the first ten minutes, I was completely checked out, lost in the noise of my own head. When she asked a simple question, and I realized I had missed the start, the frustration was sharp. I wanted to be there for her—to really be there—but my thoughts were an anchor dragging me into the past.

​Since time machines haven't been invented yet, I’m learning to be kind to the "Past Jen." She was tired, she was busy, and she was doing the very best she could. I’m choosing to fight for my own presence, not because it’s easy, but because Avery—and everyone else I love who is still here—deserves more than just the shell of me.

If you’re reading this and you still have your person—if they are right there, even if they are currently driving you up the wall with their different love language, their cut-off shirts, their sawdust, or their naps—take this as your sign. Stop waiting for the "perfect" moment of calm.

Pause.

Put down the phone.

Go find your bucket and just sit.

Prioritize the person over the productivity. Because life is made of these small, blink-and-you-miss-them moments, and trust me:

The work will always be there, but the person who is creating that sawdust won't.

You want as much of them, and as much of that quiet, uncomplicated togetherness, as you can possibly squeeze into the schedule.

A Note on the Path You Walked

Finally, I want to acknowledge that the road leading here is different for all of us. Some lost their person to a long battle with cancer; others to a sudden accident; some to tragic circumstances that leave us reeling.

The way we lost our person dictates the specific shape of our regret.

Please know that no matter the circumstances, the weight of "what if" is a common burden. There is no right way to have said goodbye, and no way to have "perfectly" navigated a tragedy. Be gentle with your story, just as I am trying to be gentle with mine.

Reflecting on Your Own "Shoulda, Coulda, Woulda"

• The "Presence vs. Production" Audit: If I could strip away the 'to-do list'—the professional goals, the maintenance, and the daily grind—what is one specific, quiet, and imperfect moment I shared with my person that I now see as a 'quality time' memory, and how can I honor that memory today?

  
  

• The Reconciliation of the "Rough Edges": I’ve spent time trying to 'edit' my relationship or my partner into a specific shape to fit my expectations. Looking back, what are the 'rough edges'—the quirks, the habits, or the personality traits I once found frustrating—that I now realize were actually the things that made our relationship uniquely ours?

  
  

• The "Bucket" Challenge: In my life right now, where is my 'bucket'? Where can I show up for the people I care about—or for myself—without trying to 'help,' 'optimize,' or 'fix' the situation, but simply by existing in their presence?