02/15/2013 03:49 pm ET Updated Feb 16, 2013

Valentine's Day: Well, This Is Awkward...

Valentine's Day is a time for chocolate, roses, love and romance -- the one day of the year when saccharine sweetness is fashionable. Cards are exchanged, dinners are shared, relationships blossom.

For many, however, the day is primed for personal embarrassment and public humiliation. That's what happens when scores of fresh-faced couples dress up, booze up, eat from overpriced prix-fixe menus and nervously contemplate the libidinous possibilities of the night ahead.

The Huffington Post asked readers to describe the embarrassing Valentine's Day moments they witnessed Thursday night. Some decided to share their own mortifying incidents instead. Below are a few.

A Washingtonian -- who wished to remain nameless -- found himself among attendees of a sex convention.

A recently divorced co-worker and I had nothing better to do so we grabbed a drink at the Washington Court Hotel. Well... Every year the hotel hosts Dark Odyssey -- a sex convention -- and it officially starts today, so everyone was arriving last night. We were the only ones there who were not there for the sexvention. I just wanted a glass of wine, but the people were all around and assuming that my coworker and I were there for it.

Gabrielle from Washington saw a date so boring one of the people on it fell asleep.

I witnessed a girl fall asleep on her date. At first, I thought she was simply mocking her boyfriend, resting her head on her chin with her eyes closed. After some time passed, it was apparent she was legitimately asleep. I watched her date throw money on the table and briskly walk out. It was probably more rude than awkward. I blame the hip, low-lit ambience and comfy oversized chairs.

Dave from New Jersey failed.

I get out of work on the later side, around 6:30 or 7. That means there are usually only gimpy flowers left with the flower guy on the corner. This year, I thought I'd found a decent bouquet of a dozen pink roses. But it was dark out, and once I got on the train I realized the flowers were already starting to die. They were black on top and the petals were falling off. I was more upset about this than my girlfriend. She said they were better than the flowers I got her last year.

Washington scribe Sam Youngman pulled a David Hasselhoff, allegedly.

KK witnessed an awkward drunk guy swooping in on a woman just seconds after she was dumped by her girlfriend.

Some of us clearly have a hard time when dateless on Valentine's Day. I'm not one of them, so when I got off work early (10pm) I walked over to my favorite local bar/restaurant for some food and a beverage. Much of the crowd was chatting about or outright ogling over a very attractive lesbian couple, one of whom had borrowed the mic from the band to dedicate a song to her girlfriend. A couple drinks later, the dedication seemed to fall to the wayside as the all-too-familiar to me "You ordered another drink??" vs "No, baby, I swear it's the same one!" back-and-forth shouting match began. I felt for the accuser and privately cheered as she stormed out, leaving the promise-breaking member of the couple alone at the bar.

Immediately, awkward "desperately in need of a friend" guy swooped in. She didn't want to talk to him. I briefly considering helping a brother out in case he'd missed the scene from five minutes earlier. But, as we all do, she needed a shoulder to cry on and lobby her case to. Two minutes later she's telling him the story, sharing current text messages and crying about her lack of a ride home. I thought briefly that there might not be anything that cringe-worthy about two lonely people sharing a beer to cry into. And then her tab came.

Seems she hadn't just been left without a ride. She had also been left with a sizable tab. When her card was declined, awkward guy whipped out his wallet and paid in full. Meanwhile, her tears had stopped and she was checking out the window as she texted. With the make-up apologies clearly underway, oblivious awkward guy helped her find her coat and walked her out...to her girlfriend's car.

Poor kid. He learned the hard way that girls who date girls aren't just killing time until the right man comes along to show them the way.

From Doug, who ran into his ex.

The funny part is over the last decade I've run into this ex completely randomly every few years with little or no contact in between. (My wife even ran into her, both naked, in the locker room at a Bikram class a few years ago.) We're all friends, but my wife was the woman I dated next after I broke it off with, let's call her "Jane."

Yesterday I was rushing for the subway when she called out my name on the street. We chatted for a minute but she could tell I was in a hurry so we exchanged numbers and I headed for the stairs. I don't know what possessed me to wish her Happy Valentine's Day as I turned to go - maybe an ill-advised attempt to be topical?

Anyway, it was not the best choice. Her response was "ugh" and I immediately felt like a clod. To top it off, when I got to the platform train service was suspended. Was that karma?

A Washington journalist drenched her date with red wine.

I spilled a tall glass of red wine across the table and onto my boyfriend. The place is quiet -- full of older, fancy people who know how to dine appropriately -- so other patrons stop and stare. A couple of them say, "ooh." The waiter swoops the glass up and says, "no more wine for the lady!" Meanwhile, half of my boyfriend's shirt is stained red. The end.

Cristina from New York thought a man was wooing her. He just wanted her cash.

A young man offered me a rose last night, and I didn't know if he wanted me to pay for it or if he was giving it to me. So I said sure and took it out of his hand; turns out he was selling it.

Wonkette's Rebecca Schoenkopf just had one of those nights.

I went out for a beautiful sushi dinner at Enya Sushi in Little Tokyo (Los Angeles). It's got a zero ambiance, it's surprisingly inexpensive, and they need customers! But I hadn't eaten lunch so I had that low-blood-sugar crankypants thing so I decided to drink a bunch of malbec in the afternoon to make up for it. I felt great!

Perfect dinner, some sake (not too much, I wasn't throwing up or anything), and then my ex-boyfriend and I went back to my apartment. We were together for three years (I was his boss; we got together on Obama Election Night, because JOY) and now we are best friends but I let him see me naked sometimes.

And then I was lying in bed crying because I will be 40 in 10 days and nobody ever married me and nobody ever wanted to have babies with me. (I have a son, but did not have him *from my vagina* and he's grown now anyway.)

And my ex-boyfriend felt REALLY bad and tried to explain that I shouldn't worry because Steve Martin just had a baby and he is 67! So my ex-boyfriend is kind of an idiot I guess. But he is my best friend and I love him very much.

We did not have any sex.

@AlexForOffice saw Die Hard 5... after a wake... by himself.

Do you have an awkward Valentine's Day story? Let us know! Email it to us at samstein@huffingtonpost.com.



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