Cupid's a Bitch: DETAILS' Editors Share Their Best and Worst (but Mostly Worst) Valentine's Day Stories

What's better than a dozen roses for Valentine's Day? A dozen juicy stories from our editors. From bad gifts to bad behavior, we share our naughtiest and nicest experiences.

Photo courtesy Corbis

What's better than a dozen roses for Valentine's Day? A dozen juicy stories from our editors. From bad gifts to bad behavior, we share our naughtiest and nicest experiences.

Jon Roth, Editorial Assistant

In my sophomore year at boarding school, I shared a suite with two other guys who talked a big game. On Valentine's Day, we all had girls over during "parietals"—the frigid, preppy version of conjugal visits, when members of the opposite sex were permitted in our rooms. Dorm rules included leaving the door cracked open 10 inches and keeping at least three feet on the floor at all times. I fudged the rules, fed my date chocolate-covered strawberries, provided a screening of Moulin Rouge (there is no surer aphrodisiac), and made it to third base. Not long after that I decided I was gay, so most of the appeal was in bragging to my roommates, who'd both struck out.

Alex Bhattacharji, Executive Editor

She was an animal lover, so it made perfect sense, our Valentine's Day trip to the Bronx Zoo. It began so well, from our boozy brunch to our laugh-filled train ride to our cotton-candy purchases—a day-long date, which, after having gone out for some time was not necessary and thus all the more appreciated. And then we came to the ape house.

We were both troubled by the imprisonment of the all-too-human gorillas, but our moods rebounded watching the gibbons play. Soon we came to a long hall that spanned the chimpanzees' windowed enclosure, and a male chimp rushed to the glass and locked his gaze on my very buttoned-up girlfriend (let's call her Lauren, as her response to the grunge-era was wearing jodhpurs to work for Polo). Our simian stalker followed us, shrieking, both his hands pounding against the glass. Then, just one hand was. The other was . . . well, otherwise engaged. As we raced for the exit, I made the mistake of laughing and she made the mistake of looking back as the chimp finished himself off, Silence of the Lambs-style.

Nojan Aminosharei, Entertainment Editor

One Valentine's Day when I was a teenager, my mother snuck into my room and placed two Hershey's Kisses on the side of my pillow right before my alarm clock was set to go off. But as a notorious snooze-abuser (my college record was a whopping 165 snoozes), I rolled over onto the Kisses and woke up an hour later with melted chocolate all over my face. The memory tickles me still, and even in the Siberia of singledom I never wake up on Valentine's Day without a chuckle.

James Oliver Cury, Online Editorial Projects Manager

It's freshman year at Stuyvesant High School—a whole new world of girls and dating and popularity contests. I'm new to all this, but somehow I muster up the courage to pursue a cute girl in the first few months of the school year and she becomes my "girlfriend." I'm thrilled, but I have no common sense about sex, intimacy, or—more important—gifting. Valentine's Day is approaching. What do I get her? Nothing. I'm not even sure I knew I was supposed to. What does she get me? A giant bouquet of carnations—red, of course, to prove her love.

The flowers arrive at 10:15 A.M. during our homeroom period. A small crowd gathers around me when they find out that I'm the stud. Yes, I have a girlfriend. Yes, she got these for me. Yes, she must really like me. My sense of self-worth has never been greater. I beam for the rest of the day and continue to glow for several months. Truth be told, I have never forgotten that feeling.

Kristen Dold, Associate Editor

In kindergarten, one of the boys in my class brought me flowers on Valentine's Day and asked me to marry him. In an extreme overreaction to my embarrassment, I acted repulsed and threw the flowers in the garbage in front of everybody. I really hurt his feelings, and I still feel really, really bad about it (Sorry, Matt). Then in college, my boyfriend at the time got me nothing, but after I gave him the stink eye, he went to the vending machine and brought back a couple of stale candy bars and left them on my bed. Le sigh. Karma is a bitch, but I still ate them.

James Gaddy, Senior Editor

I had a Valentine's Day-sucks phase in college (who doesn't?), but with girlfriends few and far between, I adopted it almost like a political stance, deluding myself that I had a choice in the matter. But one year I actually did have a girlfriend, and even though she never said anything, I could feel the pressure building. I started thinking of ways to have my chocolate and eat it, too, and eventually decided that if Hallmark could invent a holiday, I could invent a better one.

On February 13, I bought the roses, the cards, and those chalky heart-shaped candies. At dinner we toasted to the life of star-crossed lover Horatio Vespucci, the second of Amerigo's two older siblings, né Girolamo, overlooked and unsung, who lost his bride-to-be to another man, left to voyage with his younger brother, fought the rumors started by John Cabot's men, and then returned back to his village and claimed her. Anyway, I had this whole story my girlfriend humored me by pretending to believe, and the night ended up being our own private Valentine's version of Christmas Eve. We got the jump on everybody else.

Matthew Marden, Fashion Director

On Valentine's Day in the sixth grade, Megan Fencil gave me a bunch of Skittles in a Ziploc bag. While I ate them, she and her friends laughed at me. I was confused. She then told me she stuck them up her nose first. Ironically, I still love Skittles.

Sheila Monaghan, Senior Editor

Friends, it is not the thought that counts. It is the gift that counts. I'm not a materialistic person, I'm not impressed by price tags, and I ruin almost every nice thing that comes into my possession, but that doesn't mean that on Valentine's Day I think it's even remotely acceptable, let alone charming, for a man to give his girlfriend bird spikes.

Do you know what bird spikes are? They're plastic or wire spikes that you place on a windowsill to keep pigeons away—a serious annoyance for many Manhattan dwellers, particularly those whose first floor, sliver-of-a-bedroom-window opens up onto an alleyway. And that's what my ex-boyfriend got me for Valentine's Day. He wrapped them, which means he stopped at a Duane Reade after going to Home Depot to get paper but didn't see anything he thought would be a more appropriate (yet still super-crappy) gift. Nor were the spikes meant to be ironic or funny as in, "Look at the terrified face of the cartoon pigeon on the box—isn't that hilarious? I knew you'd appreciate it!" He himself was irritated by the pigeons' constant cooing and thought this would help. He needn't have worried, though. After he broke up with me, I put together a bag of his things to return to him, placing the bird spikes, unopened in their original packaging, right on top.

Jesse Ashlock, Deputy Editor

My best Valentine's Day was my last one, my seventh with the amazing woman who is now my wife. We dressed in our best and went to see a Broadway play, the steamy psycho-sexual comedy Venus in Fur. We walked out feeling that special brand of elation you get only after watching a top-notch live performance, both of us speaking in the cadences of the characters. After a martini at the Lambs Club on 44th Street, we headed downtown for a prix fixe dinner at Eleven Madison Park, where we spent the next four hours marveling at the alchemical concoctions that kept materializing before us, stealing occasional glances at the next table where Salman Rushdie was romancing some sweet nymphet. By the time we paid up we were the last ones in the restaurant. We stumbled out into the frigid February air to find a cab, high on the food and the wine and the play and the night and each other.

Greg Emmanuel, Articles Editor

One of the first Valentine's Days I spent with the woman who is now my wife looked like a home run on paper. I booked a table weeks in advance (the first and last time that happened) at one of the finest restaurants in the city. This was in those nascent pre-foodie-blog days, so I used my trusty Zagat guide to find a place rich with accolades. It was a defunct Tribeca classic that had a super-fine pedigree, but I think my desire to impress clouded my judgment.

We showed up at this culinary showplace only to find the most uptight dining room you could imagine, filled with a bunch of blue-haired ladies and their bored CEO husbands. Valentine's Day sweet-nothings were replaced with phrases like, "What is this place?" and "Why would you take me here?"

In the end, we had a really nice meal and remain happily married, but I did learn three valuable lessons: 1) I should ignore my wife's first gut overreaction. 2) You can't win on Valentine's Day. 3) Cupid's a bitch.

Laurence Lowe, Senior Editor

I was born on Valentine's Day, and there's really no one way to feel about that. It's definitely not the worst birthday you can have, but it does raise questions about best practices. Unlike Christmas babies, there isn't much guidance out there for people like me, Mayor Michael Bloomberg, and Matchbox 20's Rob Thomas. A notable exception is Frederick Douglass, the escaped slave turned great American social reformer, who never knew the actual date of his birth. (Douglass chose to celebrate his birthday on February 14 because his mother, who died when he was a boy, used to call him her "little valentine." As far as I'm concerned, this story singlehandedly redeems the whole Valentine's Day enterprise for one and all—and not just because my mom still says the same thing about me.)

Even when I was single, which was often, I didn't feel all that badly about it—except when I was young, because back then it really sucked. On the day I turned 6, I was in love with Sarah Levitt. I confessed my feelings with a heart-shaped card, but Sarah wouldn't touch it, as she was afraid of contracting my cooties. Everyone, even Ryan Gosling (who was born on November 12), knows how that feels. But because it was also my birthday, Sarah's scrunch-faced rejection exposed me to a particularly potent strain of Valentine's Day self-pity that would take only slightly more dignified forms throughout my adolescent and early teenage years. Around 16, I began to question the exclusionary nature of Valentine's Day. Later, when I finally got a girlfriend, I learned that it's sometimes best to keep these questions to yourself. Never mind the details; I had come up short that Valentine's Day, but I did have a solid birthday defense.

Stayton Bonner, Assistant Editor

In bachelorhood I dismissed Valentine's Day as a contrived holiday orchestrated to push greeting cards upon the unimaginative masses. In marriage, I've learned to keep my mouth shut. I offered cynicism, Chinese takeout, and TiVo to my wife on our inaugural February 14, only to receive indigestion and the far end of the bed in return.

And so the fragrant world of flower shops entered my smartphone-contact list, a reliable romantic Rolodex for holidays, birthdays, or the occasional Monday. I learned that white and muted flower tones sync with our loft's exposed-brick walls. I learned my wife hates roses and loves freesia. I learned to store bouquets in the bathtub at night so our cat wouldn't tear them to pieces (he also eats cigars). But most of all I learned to be a man and embrace Valentine's Day.

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