She told me she had no regrets. No regrets about her profession, or her children, or her love life, or her travels. None whatsoever.

It’s a bold statement for anyone to make, let alone someone pushing 85. It remains the most confounding yet beautiful response I’ve ever received to a sermon.

Confounding because the subject of the sermon had been … regrets and how everyone has them.

I had gone through the list of what people most regret, according to the NY Times. Lost love sits at the top of the pile, not surprisingly, but then there’s career paths, financial decisions, sibling relationships, and bad health habits, to name just a few.

I’d talked about the phenomenon of FOMO, and how it betrays a deep collective fear of regret, as opposed to, say, loss. I’d spoken about parents on the sidelines of soccer games, funneling their regrets about their own failed athletic pursuits into their children’s performances. I’d referenced a few of my own coulda-woulda-shoulda’s.

Nothing had pierced this wonderful lady’s gratitude for the life she had lived.

She’s gone now, but I think about her often. I think about her because there are very few things in life that I don’t regret. At least that’s how it often feels. It’s not that I’m ungrateful for all I’ve been given — though I probably am. It’s that, emotionally speaking, I’m much more likely to dwell on decisions I wish I’d made than the ones I did. The same goes for things I might’ve said (or not said!), people I could’ve treated better, cryptocurrencies I should’ve bought, viruses I didn’t need to contract right as the vaccine was finally becoming available. Ahem.

Neurotic as it sounds, I don’t think I’m alone.

The theologian Paul Griffiths defines regret as an “otherwise-attitude,” summed up in the statement “I would it were otherwise.” In his view, regret is less severe than contrition or repentance but not unrelated. It can be targeted at almost anything, not just moral wrongdoing. You can regret “the job you didn’t take” — and the hubris that caused you to turn it down — but you can also regret wearing shorts instead of pants.

Judith Shulevitz defines regret as “what we feel when we realize that we’ve hurt ourselves — damaged our careers, tarnished our reputations, limited our options.” This is in contrast to “remorse, which is what we feel when we’ve hurt others.”

I regret not writing about regret in Seculosity. Because a culture swimming in seculosity will be a culture in which all sorts of everyday activities have been invested with moral righteousness. The “right” spouse, the “right” school, the “right” job, the “right” diet, the “right” wellness regimen, the “right” set of cultural-political sensitivities, the “right” response to the pandemic, etc. End up with anything but the optimal outcome, and welcome to regret central.

It’s not a fun place to live. When you’ve done actual wrong, there’s the possibility of forgiveness or restitution. But when you’ve simply chosen what, looking back, might not have been the wisest or happiest option in a given situation, what can you do but rationalize or suppress? There’s nowhere to go.

The burden of regret may be lighter than that of guilt, but it adds up.

One way to silence nagging regret is distraction. This usually takes the form of busyness or self-medication. If I just keep going, keep reaching, keep cranking, then I won’t have the time to indulge that pesky “otherwise-attitude.” More than that, I’ll be minimizing possible regret by working tirelessly to narrow the gap between the “real” me and the “right” me. Win win!

Cue the pandemic, with its halting of various avenues of achievement and its forced reflection (and over-exposure to social media / under-exposure to church), and what you have are prime conditions for fostering an otherwise-attitude. A pandemic of regret, if you’ll forgive the overused phrase.

I suspect this outbreak is particularly acute among my demographic, AKA the middle-aged, AKA those of us who feel like we’ve just passed the point of no return in our various endeavors — right as our peers are reaching (what we perceive as) new peaks of prosperity. It’s hard to stifle regret when you’re constantly confronted with the lives you might have led.

Add in a dash of boredom-induced nostalgia, plus Brandy Clark’s amazing new record on repeat, and you have a pretty potent recipe for solipsism. Or so I’ve heard …

Of course, whatever your stage of life, the discomfort is compounded by a culture that demonizes regret as useless if not actively destructive. You’ve got to own your near-misses, we are told — celebrate them even! — and move on. Leave your behind in the past, Pumbaa advises.

If only, as in all things, it was as easy as knowing what we should do.

Make no mistake: regret is painful. It can handcuff a person. Imprison them in the past. It can fuel self-pity and short-circuit gratitude. It can breed despair.

Perhaps, though, we miss out on something constructive when we rush to outlaw regret altogether. No one has written more trenchantly on the subject in recent years than Jonathan Malesic:

“No regrets” sounds great on TV and shares well on social media because we equate decisiveness with importance and control. But to live proudly without regret is to ratify your own idiocy, to take unjustified self-satisfaction in your existence. Your past actions made you who you are, sure, but maybe who you are isn’t so great. Without regret, you have no way to reckon with that.

Elsewhere he observes:

Regret, including the kind that terminates in remorse, knits the old and new selves together. It gets you to recognize your solidarity with a stranger: the stranger you were, who was thoughtless or malicious or whose life was just complexly unsatisfying. Making those connections enlarges the self; it’s a necessary component of moral growth.

What he describes is almost paradoxical: genuine moral (and what I’d call spiritual) growth involves the recognition that in many ways you are still the same person you’ve always been. In this sense, carrying regret may be part and parcel of a properly low anthropology — an unavoidable aspect of life as a broken person in a broken world. As such it represents a possible pathway to compassion and connection rather than disdain.

That is, the persistence of regret ties us not only to our past selves but to other sufferers in the present. A unifying force in a world that feels more divided every day. A basis for sympathy and therefore hope.

Paul Griffiths goes further. He writes that “someone who has no regrets is someone not fully human and not much formed as a Christian.”

Hmmm … I get what he’s saying, and no doubt the gospel of grace gives a person permission to come clean about their regrets just as much as their shortcomings. But how does that square with the old lady who objected to my sermon?

While I can’t know exactly what she meant when she told me she had no regrets, I’ve developed a theory. This woman, we’ll call her Kay, was one of the kindest souls at our church and a person of real depth. She never shied away from sermons about sin or darkness — and happily eschewed self-righteousness in all its forms. I know for a fact that her ride hadn’t always been smooth.

My theory is that Kay was actually evincing a rare spiritual maturity. What you might even call holiness. She had arrived, I believe, at a heartfelt acceptance of God’s work in her life. And the chief way of discerning that work was to locate where God’s plan contradicted her own. Those points of tension, which so often serve as wellsprings of regret, could also be seen — through the eyes of faith — as evidence of God’s provision.

Where self-pity might have thrived, thankfulness blossomed instead. This is why I consider her response so beautiful. Who doesn’t envy that kind of faith?

Then again, maybe she was just losing her marbles.

Either way, I regret not knowing her better.