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Roses are red, violets are blue, Valentine’s Day is upon us, so tell me what he did to you.
That’s exactly what I asked of you, my ever-entertaining readers, friends, and followers. As the day loomed closer, I’ll be candid—I wasn’t particularly thrilled about its arrival.
This year, I’m confronting the holiday from a new perspective—single. Yes, you heard right. Cue the thoughts and prayers.
But rather than languish in singledom, I chose to embrace what Valentine’s Day truly offers: the tales of triumphs, disasters, and everything in between. Few things expose the essence of a person more than a day that demands a public display of affection.
I reached out to you, asking for your most outrageous, bizarre, delightful, and downright disastrous Valentine’s Day tales. What I received was less of a “Love Actually” moment and more akin to a session of “Group Therapy With A Stiff Drink.”
Let’s dive into the stories of those who went above and beyond.
One woman told me about a first date on Valentine’s Day where a man she’d been chatting to for weeks whisked her off to a tiny Italian restaurant lit entirely by candles. He’d pre-ordered her favorite wine because he’d remembered it from a throwaway comment she made about a trip to Florence.
Pause… a throwaway comment! Give that man a slow clap.
I am facing Valentine’s Day – gasp! – single this year
I put out a call to you to send in your wildest, weirdest, most wonderful and utterly tragic Valentine’s stories
At one point he excused himself and returned with a handwritten note thanking her for taking a chance on him. They’ve now been together for three years.
Then there was the woman who thought she was being taken to a romantic rooftop dinner. She arrived in heels and red lipstick only to discover he’d booked a ‘Valentine’s couples improv comedy workshop.’
She left midway through an exercise called ‘Sensual Vegetables,’ and ordered herself oysters at the bar next door.
Another follower told me her date presented her with a single long-stemmed rose and a speech about how ‘love is a social construct.’
He then suggested they split the bill because, and I quote: ‘Capitalism is also a social construct.’ She paid, went home and matched with his roommate on Hinge out of spite.
And then there are the sexual misadventures, because Valentine’s has a way of accelerating intimacy whether you’re ready or not.
One reader admitted she agreed to spend the night with a man she’d only been on two dates with because ‘it felt like the romantic thing to do.’ Halfway through, he stopped, looked at her very seriously, and asked if she believed they were twin flames.
She did not. She did, however, believe in Uber.
Another woman told me her Valentine’s date was so determined to impress that he booked a suite at a luxury hotel. It was all champagne and rose petals until he tried to recreate a scene he’d clearly rehearsed in his head.
Let’s just say it involved satin handcuffs, a YouTube tutorial’s worth of misplaced confidence and a mistimed ‘mount’ that ended with him in hospital. She now refers to him as ‘Fifty Shades of Crooked.’
But for every story of romantic delusion, there was one of quiet magic.
A widower in his late fifties took a woman out for her first Valentine’s since her divorce. No theatrics or grand gestures. Just a dinner where he asked her questions and listened to the answers.
She said it was the first time in years she felt seen instead of assessed.
It struck me reading these, that Valentine’s doesn’t actually test romance. It tests emotional intelligence. It reveals whether someone understands that what we want isn’t necessarily spectacle, but consideration.
It also exposes the gap between fantasy and reality.
We grow up absorbing the mythology of Valentine’s Day, and the movies and TV shows that build it up to be the most magical (or tragically sad) day of the year.
The surprise trip. The perfectly timed kiss. The chemistry that hums like a live wire. But real life is messier. Sometimes the restaurant loses your booking. Sometimes the sex is awkward and heck, sometimes the person across the table turns out to have strong opinions about cryptocurrency and no opinions about you.
We grow up absorbing the mythology of Valentine’s Day, and the movies and TV shows that build it up to be the most magical (or tragically sad) day of the year
For every story of romantic delusion, there was one of quiet magic
And yet we keep showing up.
Perhaps because even when it goes wrong, it gives us a story. And stories are their own kind of currency.
Trust me, I’ve built a career out of it.
One of my favorite submissions came from a woman who said her Valentine’s date never arrived. She sat alone for twenty minutes before realizing she’d been ghosted in real time.
Instead of crying, she ordered the tasting menu and texted her ex to thank him for at least having the decency to break up with her in person.
So for those of us navigating this Valentine’s Day solo, take heart. There are just as many couples sitting through a prix fixe dinner in simmering disappointment as there are singles relaxing in pajamas.
And honestly, wouldn’t you rather spend the evening with a Bridget Jones binge and your girlfriends than with a man who has royally stuffed it up?
And for those who are coupled up and genuinely giving it a go, remember this: the real win isn’t finding someone who performs love perfectly on cue. It’s finding someone who makes you feel steady in the chaos of it all.
Because at the end of the day, no one remembers the price of the bouquet.
They remember how they felt walking home.