The Worst Valentine’s Day Ever of Each Myers-Briggs® Personality Type

Valentine’s Day often arrives with a flurry of heart-shaped chocolates and bouquets, but it’s not always a day of celebration for everyone. For many, it can be chaotic, confusing, or even a stark reminder of the complexities of relationships. Some people may find themselves deeply in love with the romanticism and affection that the day promotes, while others dislike the commercialization or the pressure to manifest an idealized love. This difference of experiences and perspectives got me thinking about the potential for a Valentine’s Day gone awry for each of the 16 Myers-Briggs® personality types. What could be the worst version of the day specifically for each unique personality? Let’s find out!

Estimated reading time: 33 minutes

Discover the worst Valentine's Day ever of each of the 16 Myers-Briggs® personality types. #MBTI #Personality #INFJ

The Worst Valentines Day of Each Myers-Briggs® Personality Type

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The ISTJ’s Worst Valentines Day Ever

The ISTJ’s Valentine’s Day began with a surprise scavenger hunt concocted by their well-meaning partner, who thought unpredictability was the spice of life. At each stop, the ISTJ was met with a cacophony of noise—flash mobs declaring love, musicians playing loudly in intimate cafes, and noisy parades in the streets, all carefully planned by their partner who beamed with pride at their ingenuity. The stoic ISTJ, craving order and peace, felt a mounting panic as they longed for a quiet dinner at home instead of this chaotic lovefest.

In an effort to keep the “fun” going, the partner then unveiled an enormous, glittering, heart-shaped balloon that seemed as if it could be seen from space. The ISTJ, who appreciates practicality over bombast, was then asked to parade the monstrous balloon through the city as onlookers gawked and cheered. With each step, the ISTJ’s discomfort ballooned like the monstrosity they were tethered to, and the partner reveled in the attention they were smothering upon the ISTJ, who would much rather have wilted flowers or a quiet ‘I love you’.

Dinner did not fare better for the tradition-loving ISTJ. Instead of the reserved table at their favorite local diner, their partner had whisked them away to a new avant-garde restaurant where meals were deconstructed and the essence of the food was debated over in lengthy theoretical conversations. The ISTJ, preferring their meat and potatoes without existential dialogue, was roped into a debate about whether love was just a social construct, all while picking at a dish called “The Emptiness of Passion,” which suspiciously resembled foam.

The climax of the evening hit when, over dessert, the partner decided it was the perfect moment for an impulsive marriage proposal, complete with a flashmob choir and a ring hidden inside a tiny, edible concept car meant to symbolize their future journey together. With everyone’s eyes fixed on them, waiting for an emotional response, the ISTJ felt the weight of expectation to express feelings on the spot. Utterly mortified and long past the point of preserving their partner’s feelings, the ISTJ stood, pushed the concept car dessert aside, and muttered something about needing to organize their sock drawer—a clear signal the day’s spontaneity had come to an abrupt, albeit quiet, end.

Find out more about ISTJs: ISTJ vs INTJ: Which One Are You?

The ENFP’s Valentine’s Day Nightmare

The ENFP wakes up on Valentine’s Day to find themselves unwittingly enrolled in their own version of ‘Groundhog Day’—except, instead of Bill Murray and charming small-town quirks, it’s a day filled with the most soul-sucking activities imaginable. Their significant other, who prides themselves on supreme practicality, has meticulously planned every moment of the day. It begins with the “Joy of Tax Filing”—a couple’s workshop where sweet nothings are eclipsed by the seductive rustle of receipts and the intoxicating clack of calculators. The ENFP, whose spirit is as free as an unbridled mustang galloping across the plains, feels their inner child weep.

Lunch offers little respite; the couple sits at a nondescript grey office cafeteria known for its relentless commitment to serving overboiled vegetables and cardboard-esque meatloaf. During the meal, their significant other launches into a lecture on the practicality of beige and the frivolousness of the ENFP’s vibrant wardrobe. The café’s overhead lighting flickers in a hypnotic rhythm, threatening to lull the ENFP into an existential crisis, and no amount of ketchup can mask the taste of their fading dreams.

The afternoon is spent at a seminar entitled “Predictability: The Pathway to a Peaceful Life.” The ENFP, who thrives on creativity and the excitement of the new, is strapped in for hours of monotone monologues espousing the virtues of tradition, routine, and the beauty of the expected. They are handed pamphlets on how to create a more orderly existence, each page a nail in the coffin of their once vibrant, imaginative soul. To add insult to injury, their partner enthusiastically joins the discussion, citing examples of the ENFP’s past “chaotic and wasteful artistic endeavors.”

As if the day could get no worse, dinner arrives in the form of a home-cooked meal—every dish a different shade of beige, every recipe stripped of any seasoning that might offend the sensibilities of the unimaginative. The crescendo of the evening’s understated horror is a paint-by-numbers activity, where the ENFP’s partner insists that coloring within the lines will bring unparalleled satisfaction and a greater sense of life’s true meaning. The ENFP stares at the dismal image of a vase—which will invariably be colored in varying shades of grey—and wonders if their technicolor heart can endure any further compression.

Curious about ENFPs? Read 24 Signs That You’re an ENFP, The Visionary Personality Type

The ISFJ’s Worst Valentine’s Day Ever

The ISFJ’s Valentine’s day began with what was meant to be a serene couple’s painting class—think, quiet conversation and wine-sipping creativity. Yet, upon arrival, it was not the tranquil studio they envisioned. Instead, they found themselves in the midst of a paintballing session for couples, ducking and diving to avoid the splattering colors, their clothes a canvas to chaos, their senses overwhelmed by the cacophony of paintguns and shrill laughter.

Post-battlefield, looking less like a couple on a romantic date and more like abstract art rejects, the ISFJ hoped for respite. But their partner insisted on capturing this “raw, real moment” with a spontaneous couples photoshoot in the messy attire. An enthusiastic photographer directed them into wild, expressive poses amidst the park, clicking away as passersby observed the spectacle.

The ISFJ’s distress grew at dinner in a posh restaurant where a stand-up comedian performed roasts of the couples. To the ISFJ’s horror, their table was spotlighted for “a little friendly fun”—an excruciating set rife with private jokes turned public and digs about their paint-stained attire. The room roared with laughter but the friendly jabs felt more like prickling thorns.

Seeking solace in the supposed sanctuary of their home, the ISFJ was greeted by an elaborate, surprise gathering of acquaintances—not even close friends! Loud music blared from speakers, drinks spilled on their pristine floor, and a boisterous game of truth or dare commanded the center of attention. The ISFJ’s home, their haven, was a circus of uncoordinated chaos.

As the night wore on, the ISFJ felt their intimate Valentine’s Day morph into a communal affair they hadn’t signed up for. As places were exchanged and the noise swelled, their partner’s smile seemed to engage everyone but them. Burdened with a smile that didn’t quite reach their eyes, the ISFJ catered to unfamiliar guests, their sense of obligation wrestling with the desire to escape to a quiet corner with a book. Exhausted, they retreated to bed long after midnight, wondering if it was all worth the trouble.

Find out more about ISFJs: ISFJs and Their Romantic Compatibility with Every Myers-Briggs Personality Type

The ENTP’s Worst Valentine’s Day Ever

Imagine the dismay of an ENTP, whose Valentine’s Day commences not with a bang, but with a monotone whimper, courtesy of their date’s passion for philatelic history—the finer points of stamp history. As the enthusiast drones on, illustrating the minute differences between the 1840 Penny Black and the Two Pence Blue, the ENTP’s soul attempts to astral project to anywhere else. Attempts at steering the conversation towards something—anything—more scintillating are met with an enthusiastic monologue about gum adhesive varieties through the ages.

For lunch, the ENTP is ushered to a vegan, gluten-free, soy-free, taste-free café that prides itself on serving food as bland as its white-washed walls. In an effort to appease their environmentally-conscious date, the ENTP nods along to a lengthy discourse on the importance of alfalfa sprouts in a modern diet. Meanwhile, their taste buds grieve the absence of culinary adventure, and their intellect simmers in a pot of boiling disinterest.

The afternoon offers no reprieve, as the couple attends a sold-out seminar—“Coping with your cat’s emotional hypersensitivity: A deep dive.” Here, the crowd absorbs tear-jerking tales of feline existential woes while the ENTP bitterly rues the lack of logic in equating Mittens’ displeasure at her kibble’s shape with emotional depth. As the speaker gazes profoundly into the middle distance, our hero’s sarcastic commentary is lost in the wave of empathetic nods and collective purring from the audience.

Evening approaches, and dinner is presented as an intimate affair in a cozy nook of the city’s most notorious kitsch-themed eatery—”The Glitter Unicorn.” Surrounded by unicorns in varying scales of pink and an abundance of glitter that defies the laws of physics, the ENTP feels their art of debate dull in this pastel prison. Desperate attempts to kickstart a logical discussion are thwarted by the arrival of “The Serenading Cupid”—a chubby impersonator who belts out love ballads off-key, armed with a bow and suction-cupped arrows that find their mark a little too close to the ENTP’s last nerve. As the evening ends with a ceremonial dance beneath the ‘Rainbow Love Arch,’ the ENTP plots a Valentine’s Day rebellion—the following year will be spent in splendid isolation, or at the very least, free from the tyranny of unicorns and emotional pet seminars.

Read more about ENTPs: The Top 7 Gift Ideas for ENTPs

The INTJ’s Worst Valentine’s Day Ever

The INTJ’s Valentine’s Day kicked off with their partner’s heartwarming but misjudged endeavor to awaken their less prominent emotional side. Their morning coffee came with a side of serenade from a hired guitarist, bursting into their minimalist apartment. The crooner belted out love ballads that would make a Victorian poet cringe, while the INTJ sipped their coffee, longing for the usual silence they wrapped around themselves like a comforting blanket. Mid-chorus, their partner—teary-eyed by the performance—joined in, turning the duet into an emotional cacophony, as the INTJ contemplated if they could program a robot to feign emotions on their behalf.

Lunchtime arrived with the promise of calm, only to reveal the couple booked in for a ‘Heart-to-Heart’ extreme zip-lining experience, where emotional confessions are encouraged at each platform. With their partner zipping alongside, shouting words of love against the wind, bystanders cheered from below, mistaking the INTJ’s stern focus for fear rather than irritation at the blatant disregard for the personal joys of gravity. Desperate to discuss the psychological implications of adrenaline on amorous confessions, the INTJ was instead pulled into hug after soaring hug, making mental notes to redesign their partner’s idea of emotional bonding.

By late afternoon, the INTJ felt hope as they returned to their sanctuary, hoping to find peace amidst their cherished book collection. Yet they were met with the horror of their neatly organized bookshelves disheveled by their partner in search of ‘The Five Love Languages,’ ironically lost in translation among the classics. Meanwhile, friends unexpectedly flooded in for a ‘casual’ Valentine’s gathering, waving emotional self-help books and insisting on group discussions about feelings. Each time the doorbell rang, it was as if another chapter of their calm was being torn out, noisy interruptions and laughter cascading over the carefully categorized sections of their life.

Evening beckoned a retreat to the couple’s favorite intellectual hub—a quiet local library holding a Valentine’s themed poetry reading. But there was a twist; an interactive segment had the INTJ forcibly teamed up with energetic strangers, narrating poems they composed on the spot while incorporating big emotional expressions. To their abject horror, their partner—inspired by the day’s events—stood and delivered an impromptu declaration of eternal love through an overly dramatic sonnet, eliciting applause and bringing a nearby book club to tears. The INTJ, managing a tight-lipped smile, plotted a Valentine’s Day next year that involved a deserted island, or maybe a nice, quiet lunar colony.

Want to know more about INTJs? 10 Things You Should Never Say to an INTJ

The ESFP’s Worst Valentine’s Day Ever

The day of affection started with an ominous thrum for our ESFP protagonist as they awoke not to the aroma of their favorite breakfast in bed but to a stark, silent room and a daunting, heavy gift – a self-help book titled “The Art of Quiet: Find Your Inner Peace.” The horror was palpable. As an energetic ESFP, the mere thought of adopting the life of a stoic monk, to merely sit and exist, was akin to being asked to weave their own straitjacket from threads of dull inaction. The moment their partner suggested they spend the day practicing ‘mindfulness’ through various sitting poses, the ESFP’s smile strained. They already pictured themselves fashioning an escape rope from the book’s pages.

Lunchtime brought no consolation, as dear friends had apparently conspired against all that the ESFP held dear. They were dragged to a “Silence & Salad” dining experience—where speaking was strictly forbidden, and the menu was an insult to the term ‘variety’. The ESFP, always one to revel in jovial banter and a hearty meal, found themselves gesticulating wildly, trying to orchestrate a mime’s performance to communicate their need for flavor and conversational spark. Their efforts were only met with stern shushes and condescending nods, suggesting they embrace the ‘tranquility’ of their crisp, flavorless lettuce.

The afternoon seemed to plot a coup against their soul. It announced its arrival with an invitation to – wait for it – a “Knitting for Couples” workshop. The ESFP muttered a silent prayer for power-knitters to expediently knit them an invisibility cloak. With each methodical stitch and purl, the vibrant, action-craving spirit of the ESFP was tethered tighter and tighter to the chair. They cast longing glances at the window, envisioning themselves somersaulting into the freedom of the streets, away from the monotonous tyranny of yarn. Their partner’s enthusiastic cries of “Isn’t this exciting?” only rubbed salt into their fraying sanity. Why had they agreed to this relationship again?

Evening beckoned with the promise of a romantic dinner at their favorite restaurant. Finally, they could indulge in their love for good food and great company. Alas, the universe had other plans, as the evening progressed with a twist – every course of the meal was to be accompanied by a lecture on its nutritional value and mindfulness practices. Before taking a bite, the ESFP was encouraged to sit quietly and meditate on the ingredients, their origins, and their significance. Meanwhile, their partner happily raved about the benefits of kale and quinoa while the ESFP’s stomach grumbled in protest. They vowed to never again mix food with philosophy.

Defeated and starving, the ESFP resorted to stuffing their face with bread rolls for sustenance and daydreaming of their next meal at a restaurant that celebrated the joy of eating. As they paid the bill (under the guise of using the restroom), they made a mental note to plan next year’s Valentine’s Day away from anyone who suggested mindful activities or nutrition lectures.

The INFJ’s Worst Valentine’s Day Ever

Clad in their finest outfit, the INFJ set out on Valentine’s Day with the optimism of an ant who believes it’s possible to move a rubber tree plant. The omens were there when their partner crowed with delight, ushering them into a ‘Surprise Karaoke Love Tournament.’ The venue was packed like a New York subway at rush hour—just with more sequins and off-key renditions of “Endless Love.” As the microphone was thrust into their hands, the INFJ’s inner sanctuary crumbled like a house of cards in a wind tunnel, each screeching speaker violating their soul’s need for quietude and meaningful conversation. They belted out a trembling tune, all the while dreaming of being home with their favorite book and a cup of herbal tea.

Next, their partner whisked them to a family lunch that was less of group hug and more of a mixed martial arts contest for the soul. Imagine a Thanksgiving dinner, but instead of turkey, you’re served a piping hot plate of pent-up grievances. This was a symphony of discord where every family member was a soloist. Aunt Suzanne aired her dirty laundry, Uncle Bob debated politics with Grandpa Joe, which resulted in Grandma Rose reciting the Bible and praying for “family healing” at an alarming decibel. The INFJ, who naturally doubles as the resident shrink, tried to throw lifelines of empathy into the tumultuous sea of shouts, but they themselves were capsizing under the cacophony of family “fun”. It was the emotional equivalent of trying to wallpaper during a hurricane.

Afterwards, as if the day needed more sparks, the couple attended a party that was the love child of Mardi Gras and a rock concert. Our INFJ was engulfed by raucous crowds celebrating everything they abhorred—loudness, chitchat, and the distressing sense of human proximity best reserved for sardines. The noise was like performing a symphony with chainsaws, and every accidental elbow jab to their side felt like Cupid had traded his bow and arrow for a battering ram—all set against the backdrop of a playlist that shouted ‘romantic ambience’ as much as a jackhammer serenades a sunrise.

Somehow, through the hurricane of karaoke, the cacophonic family feud, and the Mardi Gras-Rock concert love child, our brave INFJ survived. But, as the evening unrolled its red carpet of torturous revelry, the INFJ plotted their escape. They feigned a sudden allergy to party balloons and confetti, gasping with the conviction of a Shakespearian actor facing their tragic end. Concerned yet slightly befuddled, the partner agreed to escort them home. Upon their hasty return, the INFJ wasted no time retreating into their sanctum sanctorum—their pristinely quiet home.

Inside, they were greeted by the sweet symphony of solitude: the distant hum of a refrigerator, the occasional creak of a comfortable house settling into the night, and the sublime absence of humans attempting to reach decibel levels that could summon dolphins. As they snuggled into their favorite armchair, book in hand, the INFJ reflected on the day’s events—each filled with good intentions yet so painfully contrary to their own idea of a perfect Valentine’s Day.

Find out more about INFJs: 24 Signs You’re an INFJ, the Mystic Personality Type

The ESTP’s Worst Valentine’s Day Ever

The ESTP’s Valentine’s Day began with the promise of adventure that quickly deflated like a misguided dart to a balloon. Their date, with eyes glistening with excitement, unveiled the day’s itinerary – a Historical Lecture on the Evolution of Handwriting. Barricaded in a room with gray walls magnifying the monotone drone of the presenter, the ESTP’s soul itched for an escape hatch. Their only savior was the clock, which seemed to tick with the lethargy of a sloth on vacation, and each minute felt like a personal affront to their need for freedom.

Lunch managed to amplify the tedium. The couple was roped into a ‘Reflective Silence Retreat’ where the only thing served faster than the raw broccoli and unseasoned tofu was the silence. Here, the ESTP’s usually sharp wit and tongue were prisoners to the vow of silence, their usual avenue of storytelling and banter blocked by an invisible force field of solemn introspection. The ESTP, known for living in the here and now, found their mind retreating into fantasies of a high-speed car chase – anything to feel the rush of spontaneity again.

The afternoon was an exercise in sedated restraint as they wandered into a Couple’s Watch-Painting Workshop, where “the beauty of time stands still,” quite literally. Armed with the tiniest of brushes, the ESTP was expected to paint intricate patterns on watch faces, engaging in a minute ‘labor of love’—which in reality was akin to performing surgery with mittens. Their partner oohed and aahed at the delicate task while the ESTP fought back yawns, their fingers itching for action that didn’t involve microscopic strokes or pained concentration.

As evening crept upon the restless ESTP, the final flourish was revealed – a ‘Fire-side Philosophical Debate’. Touted as an enlightening exchange under the stars, it quickly spiraled into an abyss of verbose pontifications and hypothetical musings. There they sat, the raw night air aglow with pretension as words like ‘existentialism’ and ‘phenomenological’ took flight, prompting eye-rolls so intense the ESTP feared they might dislodge a retina. Each puff of rhetorical fluff hovered like a cloud; a fog of dull, meandering introspection that was slowly suffocating their adrenaline-fueled essence. They made a mental bookmark on this night – to avoid future Valentine’s dates that resemble a test of endurance, rather than an expression of romance.

Discover more about ESTPs: The Flirting Style of the ESTP Personality Type

The ISTP’s Worst Valentine’s Day Ever

The ISTP’s Valentine’s Day debacle commenced with what was meant to be a gentle morning surprise but instead unfolded into an emotional ambush. As they awoke to their partner’s face hovering inches away, the ISTP was assaulted by a piercing serenade of “their song” on a kazoo. The sheer intensity of the off-key performance ushered in a level of awkwardness that could make onions cry. It was an affectionate gesture gone rogue, leaving the ISTP in a quiet yearning for the sweet reprieve of solitude and silence.

The afternoon offered no sanctuary; it propagated the day’s theme — invasions of personal space and uninvited psychoanalysis. In an ill-fated attempt to foster “intimate connection”, the ISTP found themselves cornered at a ‘Couples Therapy Crafting Corner’, binding twigs and feelings together to create ‘Symbolic Love Nests’. The ISTP fought the urge to dismantle their creation, feeling like a bird of prey caged amidst a flock of cooing doves. There was glue everywhere, and the ISTP’s partner unreservedly shared every sticky sentiment, broadcasting their unsolicited emotional insights with the group, turning the ISTP’s discomfort into public spectacle.

As evening approached, the ISTP was painstakingly enrolled in a ‘Moonlight Couples Yoga’, which promised to align more than just chakras. Ensnared on a mat, they contorted themselves into reluctant pretzels under the stars, as their partner admired how the ‘Heart Opener’ pose allowed one to become more vulnerable. The ISTP’s mind drifted to the storage bay back home, where their trusty motorcycle sat, throbbing gently for the open road — a metal machine devoid of any expectations or need for emotional contortion.

The finale of this ordeal was the pièce de résistance, a ‘Dinner under the Canopy of Love’ — a five-course meal wherein each dish came with a side order of oversharing from their now mopey partner. Thunderclouds of complaints about the world rumbled ominously, as the ISTP navigated through their partner’s monsoon of grievances. “Why do you always avoid deep conversations?” their partner pleaded, leaving the ISTP wondering if it was too late to order in a pizza instead. They silently vowed to never again fall prey to the commercial trap of Valentine’s Day, where love is served with a side order of unwanted intimacy.

Find out more about ISTPs: The Top 7 Gift Ideas for ISTPs

The ENFJ’s Worst Valentine’s Day Ever

The ENFJ’s Valentine’s Day started with what can only be described as the antithesis of heartfelt romanticism. Their alarming wake-up call wasn’t the anticipated breakfast in bed, but rather the piercing sound of the fire alarm, triggered by their partner’s failed attempt at a culinary delight. With bleary eyes and bedhead, the ENFJ found themselves comforting their smoke-inhalation-coughing companion, declaring love amidst the haze of burnt toast that wafted through the air.

Then came the gift exchange, a moment ripe with potential for thoughtful gestures. However, the ENFJ’s hope for something personal and intimate were crushed as their partner presented them with a homemade scrapbook — a collection of printed memes, all featuring cats making poor life choices. While the ENFJ plastered on a grin that could be seen as genuine only to the truly nearsighted, inside, they were reassessing their life choices, including spending Valentine’s with a person who apparently fell for the first idea on a DIY craft website.

After perusing the scrapbook and trying to laugh along to their partner’s apparent glee over the cat memes, the ENFJ held on to the last vestiges of hope for a deep, meaningful conversation to salvage the day. Perhaps they’d prepare a candlelit exchange about the meaning of life in one of their favorite restaurants! Instead, their partner excitedly told them their day was all booked up and, grinning with the triumph, queued up a reality show marathon of Jersey Shore and Toddlers in Tiaras. The ENFJ tried to quietly vacate the premises, but their partner kept telling them how much they’d been looking forward to this as a way to relax and bond as a couple. As each episode rolled in like an unstoppable wave of spray tans and gym musings, the ENFJ, known for their depth, found themselves desperately gasping for a lifeline of existential depth that was nowhere in sight.

As night fell, dinner seemed promising until the destination became clear: a fast-food joint bedecked with wilted balloons and an unsettling amount of fluorescent lighting. Their reserved ‘Love Booth’, which their partner won through a radio contest, was set amidst the ambiance of children’s birthday parties and the chaos of a misplaced ketchup squirt-gun fight. As their partner mumbled sweet nothings over a tray of soggy fries, the ENFJ was serenaded by the restaurant’s off-duty mascot — a person in a chicken suit playing a keytar. As they shared a romance-infused, grease-laden burrito, the ENFJ mused that next year’s Valentine’s might be better spent at a silent retreat… alone.

Discover more about ENFJs: 7 Ways That ENFJs Make an Impact

The ISFP’s Worst Valentine’s Day Ever

The ISFP’s day kicked off with what could be described as a surprise breakfast in bed if you consider a scalding hot coffee spilling in your lap as a side order to charred pancakes as ‘breakfast in bed’. This was the ISFP’s first brush with Hot Lap Syndrome—a condition not even remotely romantic.

But wait, there’s more! When their partner decided to show their love through the gift of a mixtape—a mixtape filled with recordings of themselves dramatically reading love poems they found by Googling “What words rhyme with ‘soulmate’?”—cringe levels soared through the roof. As each amateur sonnet butchered the concept of meter and rhyme, the ISFP grimaced with a force that could’ve cracked nuts.

Yet the real cherry on top of this sundae of awkwardness came in the guise of a Valentine’s Day party meticulously crafted by their partner to showcase the ISFP’s art – art they’d kept hidden away in their bedroom closet because it was just for them. This is an art show nobody asked for, especially the ISFP. Put on the spot, they had to navigate a sea of feigned interest and shallow interpretations of their deepest and most private personal expressions, peppered with unsolicited advice on ‘real art’ from folks who couldn’t tell a Picasso from a pizza.

As the art show ambled on, the ISFP felt waves of discomfort, knowing their raw emotions and inner musings were on full display, framed on walls they never wanted for them. But the grand finale to this distressing episode was yet to come. The partner, thriving on what they misunderstood as enthusiasm, launched into an impromptu auction of the ISFP’s art. The air thickened with awkwardness as friends and strangers held up paddles, throwing out bids on paintings that were never meant to leave the sanctuary of the closet. As each piece was ‘sold’, a little part of the ISFP’s soul felt bartered away in a bargain deal they never signed up for.

The evening segued into what their partner termed a ‘romantic scavenger hunt’, which in obscure reality was nothing more than a wild goose chase through town for items that held no significance to either of them. Retrieving a lost sock from the local laundromat and hunting down a half-eaten bagel from a bakery’s dumpster were but a few of the bizarre tasks. With each find, their partner squealed with delight, convinced they were making precious memories, while the ISFP pondered the existential question, “Is this what soulmates do?” Finally, as they unearthed a worn plush toy from under the park bench, it became clear—next year’s Valentine’s would be strictly solo, and their art would be far from the hands of strangers.

Find out more about ISFPs: 24 Signs That You’re an ISFP, the Virtuoso Personality Type

The ENTJ’s Worst Valentine’s Day Ever

For the ENTJ, the ultimate Valentine’s Day nightmare involved watching their meticulously planned itinerary crumble in the face of dismal inefficiency. The day began with what was supposed to be a romantic hot air balloon ride at dawn. The ENTJ had visualized a serene ascent into the sky, champagne in hand, greeting the sunrise with the love of their life. Instead, they found themselves standing in a soggy field, listening to the pilot explain that they were still waiting on a critical part: the balloon. It seemed procrastination was the real theme of the day, as hours ticked by without any sign of uplift, quite literally.

As if the disappeared balloon wasn’t enough, their partner unveiled a surprise – a couple’s pottery-making session. “It’s like that movie with Ghost!” declared their partner, with an eye-stretching level of earnestness that suggested this was the pinnacle of romance. The ENTJ, who viewed such amorphous and unproductive activities with the enthusiasm of attending a snail racing contest, was then subjected to an hour of squishing clay between their fingers. The resulting “sculpture” bore an uncanny resemblance to a certain male body part, which their partner seemed to find amusing and endearing. The ENTJ couldn’t wait for the next activity of stirring paint with their feet.

Then came what was meant to be a classy, quiet dinner at the city’s most renowned restaurant. The ENTJ had visions of deep conversation over a spicy and flavorful menu, paired with the finest wines. However, instead they found themselves sitting in a staunchly vegan restaurant, a place where seitan ruled supreme and tofu was king. Their biblically minimalist meal—a single artichoke heart on a bed of wild lettuce—stood a far cry from the feast they had envisioned.

As the strained music of a sitar player filled the room, their partner, fueled by the emotional tide that often accompanies feasting on legumes, unleashed an unfiltered torrent of grievances. Between sips of kombucha, their partner lamented the ENTJ’s unrelenting devotion to work—a schedule that left little room for impromptu date nights or midday messages of affection—and recited an exhaustive list of perceived neglects. From the forgotten month-to-month anniversaries to the “business tone” in personal texts, the ENTJ was served a full course of critiques that made the vegan cheese platter seem delectable in comparison. The ENTJ could only chew on the irony that their relentless pursuit of success was meant to pave the way for a brighter future for both, not drive a wedge through their present.

To cap off this festival of anticlimaxes, their partner dragged them to a local poetry slam – all about love, of course. The ENTJ’s discomfort was palpable as they were surrounded by people oozing what could only be described as emotional incontinence, reciting cringe-worthy, spontaneous haikus like “Your eyes, like the sea / After a storm, but with more / Kelp and dead fish vibes.” As the ENTJ sat there, forced to clap for what seemed like an eternity, they plotted a 12-step tactical plan to ensure that next year’s Valentine’s would involve a solitary trip to anywhere poetry and impromptu art auctions were legally prohibited.

Curious about ENTJs? Read 10 Things You Should Never Say to an ENTJ

The INTP’s Worst Valentine’s Day Ever

Wading into the emotional chaos of Valentine’s Day, the INTP had one wish: to somehow teleport to the 25th of February—far, far away from the emotional typhoon of the 14th. Instead, the INTP found themselves at a family gathering that was less romantic dinner and more akin to a taping of “The Jerry Springer Show” if the theme was “Love and Other Catastrophes.” Relatives, whose primary mode of affection was high-decibel nagging, engaged in love wars so intense, the UN would have retreated. And there, in the eye of the storm, sat our INTP, armed with nothing but a wilted rose and a frazzled expression, silently devising algorithms to calculate the exact moment things would go from bad to apocalyptic.

But the universe, with its quirky sense of humor, was just getting started. Dinner was served, and the INTP, in an ill-fated attempt to engage in “light conversation,” casually mentioned the St. Valentine’s Day Massacre—not as a romantic gesture but as an interesting historical event. Let’s just say, the ensuing silence was so thick you could cut it with a heart-shaped cookie cutter. Aunt Gertrude, always one for drama, interpreted this as a personal jab at her notoriously bad luck in love, and the INTP realized they had involuntarily tossed a grenade of awkwardness into the salad bowl.

Feeling the need to recover, the INTP tried to pivot the conversation to safer grounds—like the fascinating chemical reactions that occur in the brain during infatuation. However, their well-meaning lecture was systematically drowned out by the wails of Cousin Millie, whose latest romantic debacle was playing out in real-time over loudspeaker phone for all to hear. It was like a soap opera, with terrible reception and no ability to change the channel. The INTP’s discomfort index skyrocketed faster than Elon Musk’s ambitions for Mars, as they realized that the family’s emotional effusiveness matched the thrills of a roller coaster, minus the safety harness.

The coup de grâce? The family decided to play a “fun” game: charades, with a twist of true confessions. The INTP tried to mimic Romeo in silent desperation but was mistaken for miming a person having an allergic reaction to shellfish. As the night crescendoed with aunts and uncles airing dirty laundry with the zeal of confessional booth regulars, the INTP plotted a swift exit strategy involving a bathroom window and a pre-ordered Uber. In a night of emotional chaos, family drama, and conversation misfires, this INTP’s Valentine’s Day had all the hallmarks of a love-themed haunted house, leaving only one certainty: next year, their Valentine’s date would be a quiet corner in a library… on a different planet, if possible.

Find out more about INTPs: 24 Signs That You’re an INTP, the Prodigy Personality Type

The ESFJ’s Worst Valentine’s Day Ever

For the ESFJ, Valentine’s Day is a day to be meticulously planned down to the last petal and violin note. But as with all great plans, the Universe laughs, and it began with a less-than-romantic wakeup call: a prank buzzer in their hand, planted by their ever-so-charming roommate. There’s nothing like a jarring ZAP of electricity to zap away the mood of love.

The ESFJ had every minute timed perfectly, but their date had different ideas—starting with a joke about showing up fashionably late… by three hours, and not fashionably, but rather with a fashion that screamed “I got dressed in the dark… in 1986”. The ESFJ, holding back tears and the overwhelming desire to re-iron their perfectly pressed outfit, welcomed their date with warmth, which was immediately shot down by an accusation of trying to “manipulate into getting a better gift.” Ah, the sweet smell of misjudgment, almost as strong as the cologne that the date bathed in—Eau de Desperation, maybe?

The evening, already skating on the thin ice of disaster, took a nosedive into the surreal when the ESFJ’s meticulously chosen restaurant turned out to be hosting an “Exes Anonymous” support group. Picture it: dim lighting, soft music, and every few minutes, someone stands up and says, “Hi, I’m Jared, and it’s been three months since I last Facebook-stalked my ex.” The only things missing were divorce lawyers handing out business cards by candlelight.

Just when the ESFJ thought the evening couldn’t spiral to any further depths, their date decided to up the ante by unleashing an unsavory rant on the unsuspecting waitstaff over the audacity to serve water without a lemon slice—as if it was a personal affront on par with a Shakespearean betrayal. The tirade which included words like “incompetence” and phrases like “I could get better service at a kid’s birthday party!” was delivered with the flair of an amateur actor going for an Oscar in the category of “Best Performance by a Jerk in a Dining Scene.” Mortified, the ESFJ, in a moment of sheer panic, improvised an escape plan involving a fake phone call from a non-existent neighbor about an imagined crisis concerning a pet—a pet that they didn’t even own. With apologies cascading out of their mouth faster than the date’s grievances, the ESFJ made a beeline for the door, not even looking back as they vowed to turn Valentine’s Day into just another Tuesday with a side order of “No Dates Allowed.”

The INFP’s Worst Valentine’s Day Ever

The INFP’s Valentine’s escapade started off predictably quirky, with the kind of optimism that only an INFP, cradling an armful of second-hand poetry books, could muster. Their date, found through a dating app that promised deep connections based on book preferences, turned out to be someone who thought “Orwellian” meant related to Orville Redenbacher’s popcorn. Over dinner, in a restaurant with more neon than the Las Vegas Strip, their date leaned in and whispered what they thought was an intellectual insight, “Did you know, like, the Earth is definitely flat because if it were round, like, we’d all fall off?” The INFP, stifling a sob into their tofu burger (ordered for them by their date), added one more item to their already long list of “Reasons Why I Should Become a Hermit.”

As if the flat earth debate wasn’t enough to drive the nail into the coffin of romance, the INFP’s eyes darted desperately around the restaurant, hoping for a distraction. That’s when the magician showed up. A magician, inexplicably booked on Valentine’s Day to perform tricks that most certainly didn’t involve making awkward dates disappear. Instead, the magician pulled out his pièce de résistance, a trick involving live doves, a lighter, and what can only be described as a misunderstanding of the word “astonishment.” Unfortunately, the trick concluded with a charred feather floating romantically down to rest atop the INFP’s crème brûlée, turning their dessert into a scene from a bird-themed horror film.

With the evening’s entertainment traumatically burned into their memory, the INFP hoped for a reprieve as they chose to take a moonlit walk. However, their date had a different idea and suddenly revealed an aggressive passion for power-walking. The INFP, being dragged along like a shopping cart with a wonky wheel, tried to steer the conversation into something remotely meaningful. They pointed out constellations, only to be corrected that those were, in fact, “government surveillance drones”. And with the romance of an informant, the date pontificated at length about the superiority of Velcro shoes over all other fastenings—a monologue that somehow managed to elude charm completely.

Returning home, the INFP’s door slams, and they are greeted by the deafening silence of their cat, Mr. Whiskerpoof, who is by comparison a paragon of intellectual stimulation. With a heavy heart, the INFP reflected on the night’s events and concluded that Valentine’s Day, henceforth, would be an occasion dedicated to solitary poetic musings and quality time with Mr. Whiskerpoof, who, bless his soul, has never once tried to make her power-walk anywhere.

Discover more about INFPs: INFPs and Their Compatibility with Every Myers-Briggs® Personality Type

The ESTJ’s Worst Valentine’s Day Disaster

The story of the ESTJ’s Valentine’s Day is one to be entered into the Hall of Infamy, to be whispered about in the hallowed halls of dating disaster legends. It began with what one could generously call an ‘artistic interpretation’ of punctuality. The ESTJ arrived at the agreed-upon rendezvous—a trendy little café with pretensions of grandeur that served lattes more complicated than Rubik’s cubes—timing their appearance down to the second, only to be met with a space as empty as their date’s assurances of being “right around the corner. As the minutes ticked by, our ESTJ’s well-scheduled world began to crumble like a stale scone at a discount bakery.

When the date finally arrived—hair disheveled in a manner that suggested a recent tussle with a low-speed ceiling fan—the ESTJ was served a piping hot cup of frustration. It quickly became clear that their date’s personality was more artificial than the sweetener in their coffee. Speaking with the sort of conviction often seen in people who spend too much time curating their Instagram persona, they began spinning tales of their ‘big-time’ job and ‘vital’ social media influence. To the ESTJ, this charade was less appealing than eating a bouquet of roses, thorns and all.

Then came the meal, an ordeal made no less challenging by the date’s insistence on detailing every single one of their life’s woes—none of which, apparently, could be attributed to any personal failings. The ESTJ sat there, listening to the monologue of self-pity, thinking that even a tax audit performed by a dentist would be more enjoyable. And as the after-dinner mints arrived, signaling the meal’s merciful end, the date leaned back, shrugged, and said, “I don’t believe in wallets or responsibilities.” The ESTJ’s eyes narrowed, and the battle cry of “Check, please!” echoed in their soul.

The ESTJ stepped out into the crisp night air, their steps echoing with the kind of precise rhythm that only comes from a person eager to restore order. The drive home was quiet, their mind alighting upon each moment of the evening, filing it away under ‘lessons learned’. Once home, the therapeutic process of organizational catharsis began. Out came the label maker, the to-do lists, and the trusty planner. They indulged in the quiet satisfaction of color-coding their schedule, harmonizing appointments, and aligning tasks with efficiency that calms their rapidly-beating heart. With each item neatly tucked into its rightful place, a semblance of peace descended upon the ESTJ. The chaos of the evening was distilled into a series of action items, transforming disarray into a neatly outlined plan for the days ahead.

Find out more about ESTJs: 24 Signs That You’re an ESTJ Personality Type

What Are Your Thoughts?

Did you enjoy this article? Do you have any Valentine’s Day disasters you’d like to share in the comments? Let us know!

Find out more about your personality type in our eBooks, Discovering You: Unlocking the Power of Personality Type,  The INFJ – Understanding the Mystic, The INTJ – Understanding the Strategist, and The INFP – Understanding the Dreamer. You can also connect with me via FacebookInstagram, or Twitter!

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  1. As an INTP I could take or leave Valentine’s Day…my husband (not sure of his type) considers it a “made up” holiday and insists he doesn’t need the economy to tell him when to buy me flowers. And so in 23 (almost 24) years of marriage we’ve never “done” the Valentine thing, with the hassle of getting a table at our chosen restaurant, having to pick out saccharin greeting cards and the social expectation of more interesting plans for the evening than crashing on the couch to watch reruns.

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