coulda woulda shoulda
on august longing, the romanticism of regret, and self-sabotage by a million what ifs
Note: This post was originally written at the tail end of August, and I intended to publish it then. But life got in the way (as it often does), so I am publishing it now. Much has shifted since the start of September, but this piece reflects the very real pains of August, so I am publishing it as a reflection of that moment in time.
This one is also a bit longer since I have included film, book, & essay recommendations for anyone romanticizing the past at the bottom of this post. As always, thanks for reading!
Despite all the astrological forecasts, despite the weather, and despite my better judgment, I had high hopes for August. I wanted August to be pure movement — a series of epiphanies unfolding into one long movie-montage of clarity after a summer of unrelenting uncertainty.
A truth: Next month, I will leave my apartment of three years. I will leave Washington, D.C, a city I have called home for five years. Corollary: I still have no idea where I am going, where I will inhabit next. I will be lease-less, my entire life reduced to the confines of a 10x10 storage unit.
All this uncertainty has me clinging to the familiar comfort of the past. Or more specifically, my nostalgia for what could have been. Would have been. Should have been. Coulda, woulda, shoulda. It’s an old siren song. One that seems to hit me during the dog days of summer every year.
August is the woe is me of months. Perhaps it’s the lingering heat. Or the claustrophobic humidity. Or maybe it’s the realization that summer’s laziness is beginning to sour on us. With August came the start of shorter days, and with less sunlight and more afternoon storms came an intense longing for the past. Or for the imagined past. The past that never was.
Every year I get to August, and every August I am filled with longing. But none more intensely than this August with its promised transition from a secure, albeit dull certainty to the terrifying, expansive unknown. In some ways, this sense of possibility is exciting, but anyone who has looked uncertainty squarely in the eye knows how debilitating the anxiety of an unknown path can feel at times.
The truth is I gave myself until August to figure out my next steps. August was my month of clarity — I could feel it. I was certain that by August, I would know, I would just know the direction I needed to move toward next.
But August tricked me like she always does. She did not bring clarity or change or sudden movement with her this year. No, August walked right into my home and dumped her baggage all over the floor. And then, with all the audacity of an entitled toddler, she demanded I clean it up.
I examined her mess and saw she had only packed my regrets in her suitcase. Among her scattered baggage: All the lives I could not live. All the paths I did not follow. All the times a person or a job or the internet lured me away from myself. Yes, all the crushing almost past lives and moments where the universe handed me opportunities — hidden gifts I mistook for curses, so I smashed them.
Gifts like all the ideas I did not take action on — the ones I ruminated on for weeks before abandoning, the ones I ignored despite their recurrent insistence, the ones I let float out into the ether. Gifts like moments of possible connection, where I let my own self-consciousness dictate my reaction to other people. Even the gifts of new horizons. The time and money to finally travel, but the lack of nerve to do so alone. All the universe’s hints: Talk to this person! Go to this place! Publish this idea! Little gifts from the universe that I quickly returned to sender.
In August, I let myself fall down the rabbit hole of my own longing for the choices and changes I failed to make in the past. I let myself stew in my regrets. Pity party, table for one!
But every life comes with a postscript of regrets. I will never understand the people shouting “no regrets” from their rooftops. I may have cheered to “no regrets” before throwing back a tequila shot, but I have them in spades. A regret is a path not taken. An opportunity cost. The boy I didn’t kiss. The job I took too long to quit. The trip I didn’t take before the world shut down. Regrets are as normal and as pedestrian as a weekly grocery list.
Sometimes I think regrets are the easiest thing about life. Because they exist only in our heads. They’re attached to completely made up stories about our futures, and we use our regrets to justify our current frustrations with life. If only we had taken the job, kissed the boy, booked the flight, well, then, we would be different people. We would have different lives, ones free of all problems. Right?
The truth is regrets are for the romantics of life (of which, sadly, I am one). And us romantics derive pleasure from looking back on all the sliding-doors “what if” moments of the past, reconstructing alternative futures for ourselves, rather than simply sitting with our griefs and moving on.
But regret is a small house fly compared to the albatross that is grief. When grief shows up, you know it’s time to face the music of your own life.
Grief brings confrontation. The sense that time is a passing ship, and life is only ever a question of continuous participation. Will you opt-in, or will you hide under your covers and avoid the pain of living? Regret is easy, often imaginary. Grief is real, tangible. Like an unexpected punch to the gut, grief demands our attention. And grief can only come knocking so many times before she kicks down our door. It seems August delivered her to me with a clear message: face your shit.
And as I start packing my life into boxes, I’m doing just that. Facing my shit. Making peace with the past. Letting myself feel the heaviness of old expectations, of dreams that did not come to fruition, of romanticizing the past that never was and never will be. And with all the power of the world’s most enlightened yogi, exhaling and letting it all go.
I realize that one day, this time of transition will be another moment of the past, another moment I will likely romanticize in the future. So why not enjoy it? Why not drop the couldas, wouldas, shouldas of my past lives and look the present right in the face? After all, today’s possibilities make for a worthy adversary to yesterday’s regrets.
Ah, there it is: clarity at last.
Post-Script
A few nostalgic recommendations for those coulda, woulda, shoulda pity party days.
Films
Past Lives (2023)
What’s more heartbreaking than feeling haunted by someone who is still alive? How about two souls crossing paths over many lifetimes, like parallel lines destined to run alongside each other but never intersect? Past Lives reflects this pain through the aftermath of a childhood love interrupted by the cruelty of change.
Past Lives is beautiful in its nostalgic glory. In many ways, it is the perfect film. It’s quick, but it packs an emotional punch. It presents two very kind, very honest romantic options for Greta Lee’s Nora, making it difficult to root for a clean singular outcome. I think it may be the ultimate coulda, woulda, shoulda film.
Lost in Translation (2003)
Two vulnerable people in a foreign place find each other….but, oh no, it cannot last! It cannot even begin! This movie wrecks me every time. There is something terribly painful about the inevitable pain of incongruent connections. In this case, a significant age gap and two marriages stand in the way of happily ever after. And yet, no one can deny the genuine connection between Bill Murray’s Bob and Scarlett Johansson’s Charlotte (at least, I can’t. I’m sure there is a think-piece on some corner of the internet proclaiming the film problematic, but I find it both honest and compelling.)
Lost in Translation reminds us that we cannot control who captures our heart, and more importantly, it shows the devastating reality of connections that must remain within their own contextual realm. It makes me think of that Rumi line, Out beyond ideas of wrongdoing and rightdoing, there is a field. I’ll meet you there.
Before Sunrise, Before Sunset, & Before Midnight (1995, 2004, & 2013)
The Holy Trinity of coulda, woulda, shoulda!! If you have not seen this series and consider yourself a fellow creature of nostalgia, then by all means, prepare yourself for the godfather of romantic longing films. Ethan Hawke’s Jesse and Julie Delpy’s Celine meet on a train from Paris to Vienna and spend an entire day wandering the city, disclosing their greatest secrets, and possibly definitely falling in love. The dialogue is impeccable in its simplicity. And even when the characters are not speaking, their eye contact communicates everything we need to know.
What I love most about this series is you can feel the characters’ sense of nostalgia for the present moment as it passes before them. I will not disclose the plots of the follow-up films (because well, spoilers), but I will say, each sequel took place exactly nine years after the preceding film. (That’s 18 years of devotion to this series. What a commitment by Linklater and the cast! And the antithesis of instant gratification.)
Books & Essays
Stoner by John Williams (1965)
“Sometimes, immersed in his books, there would come to him the awareness of all that he did not know, of all that he had not read; and the serenity for which he labored was shattered as he realized the little time he had in life to read so much, to learn what he had to know.”
Stoner is hands-down one of the best books I have ever read. Mainly because it is a recollection of a man’s entire life. As the reader, you experience his moments of triumph, observe the forks in his path, and bear witness to the times he fails to act in his best interest, as well as the times life did not reward his attempts at courage. It’s a beautiful book, and while it does have a coulda, woulda, shoulda flavor at times, it is also a reminder that each life is miraculous and worth recounting simply because it existed at all.
Anna Karenina by Leo Tolstoy (1878)
“Sometimes she did not know what she feared, what she desired: whether she feared or desired what had been or what would be, and precisely what she desired, she did not know.”
Anna Karenina is kind of my OG woman-longing-for-another-life book. It’s everyone’s OG woman-longing-for-another life book. The story is past iconic at this point, but to sum it up, a married woman (the titular Anna Karenina) falls in love with a young cavalry officer (the infamous Count Vronsky!). Instead of keeping the affair low-key, she decides to leave her husband (the cold and bureaucratic Alexei Karenin). Oh, and this is all going down in late 19th century Russia. So, who do you think gets all the blame? There’s a reason this book ends the way it does.
Anna Karenina is a great early fall read. But it’s also a great “dead of winter, everything is dark and gloomy” read. And since August is now as brutal as January in its weather patterns, I am tempted to make the case that it is a great dog days of summer read as well.
Love Calls, and So Does the Priesthood by Katie Shepherd (2017)
“‘There are just some people who plug you into your own life,’” she said, slurring her words. ‘There’s just some people who can do that.’”
In this Modern Love essay, Katie Shepherd recounts her intimate friendship with a local Priest-in-training. Confessions are made. Intimacies occur. Heartbreak ensues.
The essay also includes one of my favorite lines of writing I have ever read (interestingly enough, it’s a quote from the writer’s friend, included in the essay and referenced above, but I love how Shepherd weaves it into the narrative). Because yes, some people do plug you into your own life! They force you out of your head and into the present moment, electrifying your days with their attention. It’s painful when these people leave us, in one way or another.
This essay also pairs well as a follow-up to a season 2 Fleabag binge. Shot, meet chaser!
P.P.S. I could probably come up with 30 other recommendations for media that romanticizes our longings and sense of displacement during transitional times. But for the sake of space, I’ll end here. Please feel free to comment your recommendations as well and/or DM me for any additional suggestions.
Love, Liv <3