Author’s Note — August 2026

I recently stumbled across this piece, originally written in 2019, and had forgotten about it entirely. I was delighted to rediscover it because, quite frankly, it’s hilarious.

Apparently, Past Me coped with the unfamiliarity of “heartbreak” by overworking, becoming deeply suspicious of fairy tales, and conducting unsolicited critical reviews of breakup songs…

Naturally, I had to share. If nothing else, this little stream of consciousness is a remarkably accurate character study—especially considering I’m not always the most self-aware person in the room. It is very on-brand for my perceived personality and innate characteristics, while sharing something of such a candid, personal nature is very off-brand for yours truly…

I remember laughing as I wrote it that night, and upon rereading it last night, seven-plus years later, I laughed just as hard—probably harder.

A Highly Unscientific Examination of Breakup Playlists, Heartbreak, and Questionable Coping Mechanisms written by Christy Chilton, circa early 2019.

I am sitting here when I should be working.

Actually, that’s a lie. I should be sleeping.

But inspiration has rarely had the decency to arrive before 10 p.m., so apparently we’re doing this instead. I’ll go to bed after I finish this entirely necessary little blurb—which, based on prior experience, means sometime between “reasonable adult bedtime” and “why are birds already making noise?”

I have been working almost obscenely hard lately. Partly because, like most American citizens, I enjoy such frivolities as paying bills and remaining solvent. But lately there has been an additional motivation behind the already fairly intense work ethic: keeping my mind sufficiently occupied that it does not wander backward into sentimental archaeology involving a man who may or may not have conned me into developing actual feelings for him.

Or perhaps, more accurately, feelings for the idea of him.

The distinction is becoming increasingly important.
I have recently developed a theory that perhaps he was not, in fact, some extraordinary man who inspired extraordinary emotions in me.

Perhaps he was just a very good con man.

Which, admittedly, is less romantic.

But considerably more plausible.

Maybe what I mistook for deep passion, profound connection, “true love,” or whatever other phrase belongs embroidered onto a decorative pillow at Hallmark was actually a rather impressive psychological cocktail of insecurity, attachment, neediness, intermittent reinforcement and all of those other hideous little words that start turning up when one Googles “what the fuck just happened to me?”

Because I simply cannot imagine that genuine love—“true love,” whatever the hell that is—is supposed to be quite this much of a pain in the ass.

Particularly when, at least from my side of things, my intentions were honest, my actions were sincere, and I behaved consistently with all of the things we had promised one another.

God.

I physically cringed typing that sentence.

“All of the things we had promised one another.”

My nose actually wrinkled.

Promises.

Who says shit like that?

More importantly, who the fuck believes it?

Apparently, for a brief but deeply embarrassing period of my life:

Me.

This may actually be the most disturbing revelation to come out of the entire ordeal.

Because in remarkably recent history, I had become That Girl.

I had somehow become accustomed to an entire romantic mythology that, stripped down to its most embarrassing essentials, sounded something like this:

“Forever.”

“We made promises to each other.”

“He swept me off my feet.”

“I fell before I even realized I was falling.”

Not necessarily those exact words, but close enough in spirit to be deeply concerning.

With very little irony.

Sometimes coyly.

Sometimes sincerely.

Sometimes—God forgive me—with an actual smile.

You get the picture.

I had somehow begun casually speaking the language of women in jewelry commercials.

These were precisely the phrases, clichés and gag-inducing romantic idioms I had spent most of my adult life instinctively scoffing at. And yet, through some combination of repetitive relationship brainwashing and what I can only assume was an unrecognized period of emotional vulnerability, I eventually succumbed.

Not reluctantly, either.

Wholeheartedly.

I bought the Cinderella story.

I may, at one particularly compromised point, have even entertained some variation of the knight-in-shining-armor mythology—which is especially humiliating because I have never particularly needed rescuing and generally become suspicious when someone arrives carrying a sword and making promises.

But I apparently thought it had finally happened.

“It.”

That mysterious event women have been assured exists since approximately the invention of fairy tales.

The perpetually independent woman had finally met The Man.

Cue swelling orchestral music.

Fade to castle.

Roll credits.

Except, obviously, the credits did not roll.

Instead, there was apparently a sequel no one asked for.

Looking back, the irony is almost impressive.

This is coming from the woman who instinctively developed the concept behind FemmeMogul specifically to empower women—not to hate men, not to compete with men for sport, but to strengthen women intellectually, professionally, financially and personally so that the playing field becomes a little more level.

I have spent most of my adult life elbowing my way through a world crowded with horny, immature men in both professional and social settings, learning fairly early how to identify bullshit from a respectable distance.

I had witnessed enough infidelity, dishonesty and fickle-hearted behavior from the sidelines - often courtesy of men who seemed remarkably unconcerned with whether or not they were actually single- to make Cinderella look at Prince Charming, then at the castle, then at the glass slipper, and say:

“You know what? The stepmother is difficult, but at least I know what I’m dealing with.”

And somehow I still got taken in by the fairy tale.

Excellent.

Humbling.

Very on-brand for the universe.

(I am getting extremely tired now, which is probably good. But writing some of this out does make the entire thing feel a little less dramatic and a little more absurd—which, frankly, is where I prefer my emotional trauma whenever possible.)

The funniest part is that none of this was actually what I sat down to write about.

I started writing because I accidentally discovered the phenomenon of the breakup playlist.

And I have questions.

Primarily:

Who the fuck makes these things?

Who voluntarily sits down and thinks:

“You know what would really help me tonight? Three consecutive hours of songs about longing, loss, abandonment, regret, shattered promises, empty beds, rain on windows and the irreversible death of everything I once believed in.”

Who assembles this?

Do they have refreshments?

Is there an intermission?

Because I genuinely feel bad for whoever remains trapped in that emotional headspace long enough to create one.

I have certainly cried during this stupid little lesson in personal development. I am not claiming emotional invincibility. There have been tears. There have been moments. There have probably been mascara casualties.

But never—not once—did I think:

“You know what this situation needs? Adele.”

Because what exactly is three hours of devastating music supposed to accomplish?

Or three minutes, frankly?

Am I trying to heal, or am I trying to turn a disappointing relationship into the final scene of Titanic?

Apparently, though, breakup playlists serve one genuinely valuable purpose: after enough exposure, they become fucking hilarious.

Take Passenger’s “Let Her Go.”

Ladies, if you are feeling even mildly bitter, this one has potential.

The basic premise is that a man finally recognizes the value of a woman after losing her and then spends the remainder of his existence wandering around haunted by this revelation.

Now that I can work with.

Nothing wrong with occasionally imagining your ex staring wistfully through a rain-covered window as the devastating realization slowly dawns that he has made the greatest mistake of his life.

Or, more broadly, letting the hurt, vulnerable or jilted person in the story enjoy a brief, entirely imaginary moment of being vindicated while the person who fumbled them experiences the full cinematic weight of the consequences.

Is that emotionally mature?

Probably not.

Is it satisfying?

Absolutely.

And somewhere during tonight’s accidental expedition through the Department of Musical Romantic Catastrophe, I realized I was no longer sad.

I was laughing.

At the songs.

At the relationship.

At myself.

At the astonishing amount of human energy dedicated to making failed romance sound like the fall of Rome.

So, before my eyes completely close, a few highlights from tonight’s journey:

James Blunt — “Goodbye My Lover”

This one must actually be heard because merely typing the lyrics cannot adequately communicate the level of emotional devastation being attempted here.

It is not a breakup song.

It is a Victorian deathbed scene.

Someone has died.

Possibly everyone.

I made it as long as I could.

Adele — “Someone Like You”

“Guess she gave you things, I didn't give to you
I hate to turn up out of the blue, uninvited
But I couldn't stay away, I couldn't fight it
I had hoped you'd see my face
And that you'd be reminded that for me, it isn't over
Never mind, I'll find someone like you
I wish nothing but the best for you, too
"Don't forget me, " I beg”

Years later and we are still desperately in love with the person who rejected us?

Absolutely fucking not.

Adele, sweetheart, I respect the talent immensely, but at some point we are changing our phone number, getting a haircut and going to brunch.

Bruno Mars — “When I Was Your Man”

Bruno’s contribution to the Great Canon of Male Regret.

He should have bought the flowers.

He should have held her hand.

He should have danced with her.

Yes, Bruno.

You probably should have.

Unfortunately, you have now realized this through piano.

There is something almost charming about the effort, although I am going to assume Bruno Mars has never read Wuthering Heights and leave it there.

No Doubt- “Don’t Speak”

Now Gwen, I understand.

Gwen is not interested in a four-hour relationship autopsy.

She does not want your explanation.

She does not require the PowerPoint presentation.

She would actually prefer that you stop talking.

Immediately.

Honestly, this may be the healthiest song on the playlist.

Silently part ways.

Hydrate.

Continue Living.

Eminem & Rihanna — “Love the Way You Lie”

I have absolutely no desire to psychoanalyze the relationship depicted here beyond observing that there are almost certainly several domestic -disturbances incident numbers associated with it.
This is not romance.

This is evidence.

Adele - “Hello”

Adele.

Again?

It has once again been years.

At this point I am less concerned about the relationship and more concerned about your unwillingness to delete the contact.

We must move forward, darling.

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Gotye — “Somebody That I Used to Know”

I do not have a clever analysis of this relationship because attempting to determine what was actually happening between these two people makes me profoundly uncomfortable.

They both seem upset.

Neither seems particularly surprised.

Communication was apparently poor.

The entire situation feels vaguely like something I have accidentally walked into and should quietly back away from.

Taylor Swift- “Look What You Made Me Do”

Taylor Swift — “Look What You Made Me Do”

Taylor Swift — “Look What You Made Me Do”

Finally.

Someone angry.

Apparently Taylor had to die, become a zombie and undergo some manner of metaphorical reincarnation to survive the breakup, which seems unnecessarily labor-intensive.

Reincarnation would probably be the more tasteful option if given the choice.

Still:

The woman is moving on.

Aggressively.

Possibly with legal counsel.

I support it.

Justin Bieber- “Love Yourself”

Now this is more my speed.

Tart.

A little bitter.

Just enough emotional honesty to demonstrate personal growth, immediately followed by enough arrogance to prevent anyone from mistaking it for vulnerability.

He reflects.

He acknowledges.

He dismisses.

He leaves.

All while somehow maintaining the energy of a mildly flirtatious asshole.

Well played, Bieber.

And perhaps that is tonight’s extremely profound conclusion.

Playlist creators of the world: I am sorry for whatever happened to you.

Truly.

But thank you.

Because somewhere between James Blunt emotionally collapsing at a piano and Adele apparently still calling someone several fiscal years after the relationship ended, I realized something rather comforting:

The whole fucking thing is a little ridiculous.

Not that love is ridiculous.

Not that heartbreak isn’t real.

Not that losing someone—or losing who you believed someone was—doesn’t hurt like hell.

It does.

But we have a remarkable tendency, when standing in the middle of it, to turn heartbreak into mythology.

Suddenly it is destiny.

Betrayal.

True Love Lost.

The Great Tragedy.

The Person Who Changed Everything.

Maybe sometimes it is.

But sometimes a relationship simply fails.

Sometimes someone disappoints you.

Sometimes you were temporarily naïve.

Sometimes a person sold you a story and, for reasons you will eventually understand, you bought it.

And sometimes the most useful thing you can do afterward is work very hard, learn something about yourself, get your sense of humor back and eventually recognize that the man you thought was Prince Charming may simply have been some guy with excellent salesmanship and unusually convincing armor.

Life goes on.

It is not always as dramatic as it feels while you are living through it.

And if I ever begin talking sincerely about “forever” again, someone please put on James Blunt.

Apparently that should snap me right out of it.

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Apparently This Situation Called for Adele