For many of us, the word “date” reminds us of nervous high-school moments, our first dinner with our eventual mate, that first time after a divorce we agreed to have a drink with someone new. But almost all of us have had dates we call “bad.” But what about those that go beyond bad? Not the awkward date that left you talking about the weather the whole time, but the one that you try not to remember even years later.

But now, you might just have some incentive to remember it. You might even win $1000.00.

My Very Worst Date has been chronicling such dates for over a year, and has been featured in TIME, Glamour, and Current, which marveled: “Bad dates can be painful, embarrassing, and make you wish you were dead. But they usually make for hilarious retellings after the humiliation and heartbreak have passed. And so, like anything that’s worth telling your friends about these days, someone has made a website dedicated to the best of the worst.”

“We strongly believe that airing our (and other peoples) courtship disasters provides comedy, comfort and cautionary tales to bear in mind the next time you say ‘yes’ to drinks with a mysterious stranger,” the site’s manifesto reads.

Just in time for Valentine’s Day comes the“Search For The Very Worst Date In America”: “The best of the worst gets a $1,000 cash prize,” said journalist Jessica Ramakrishnan, who co-founded WVWD last year with a colleague after the two realized that even just between them, there was comedy and tragedy perfect for such bite-size tastes.

WVFC asked Ramakrishnan if all the voices on the site from younger women (complete with phrases like a hot guy and We dated for months via IM, e.g. instant messages) meant that women over 40 were unlikely to see themselves on My Very Worst Date. She laughed and told us that “dating” hell is kind of universal.

“There is a universal theme that runs through the stories we get in,” said Ramakrishnan, ” and we do have a diverse lot of readers and contributors — all ages, starting with 18, and including gay guys, lesbians and perhaps surprisingly to some, a lot of straight men.” Women, perhaps, remember some of the most absurd details — even if they occurred 20 years ago. Last Valentine’s Day, for example, one wrote of a long-ago experience with anonymous dating:

Before internet dating became the norm, I signed up with a matchmaking service, which featured 3-ring binders full of members’ one-page profiles that included pictures. I picked out a decent-looking guy in his early 40’s with interests and attributes I liked and we arranged to go on a date. So in walks this guy, who had to be in his 60’s, with a horribly bad toupee and he makes a beeline for me. At this point, I wanted to die but I decided to be polite and not walk out so, instead, we sat down for dinner. Big mistake. I don’t even remember what we talked about during dinner because all I could hear was the whistling coming from his ill-fitting upper dental plate every time he spoke. Since I didn’t walk out on him or take him to task for lying on his profile, which I now suspect other women had justifiably done, he took this to mean that I liked him and hounded me with phone calls that I managed to avoid for weeks until one late night at work. I quickly pretended that my phone was malfunctioning and that I couldn’t hear who was on the other end of the line. He kept saying, “I know you can hear me,” upper plate whistling all the while through the speakerphone. At least, he never called again!

Ramakrishnan adds that dating’s deceptions and misunderstandings can be both comic and profound. “Leaving aside the stories about the seriously socially awkward, uncontrollable bodily functions (projectile vomit) and insane situations, most all our Very Worst Dates happened because there was miscommunication on some level,” she said.  “And outright lying, as on online dating profiles or about marital status, is very much part of that. People seem to be happy to fudge the facts to make themselves look better at any age.” This can even take place with old friends — at least if you meet up with them again via social networks.

I found an old high school friend on Facebook, who was single. I was single and we decided to try and get together. My birthday was coming up and he flew out to celebrate with me. Being that he was only a friend, I invited him to stay at my house, like I would with any other old friend. The arrangements were that he would take my room and I would sleep in my 17 year-old son’s room. The weekend was going well and we were really hitting it off. He wore a football championship ring, similar to a Super Bowl ring. But, he only went to community college and never even finished and now is a prosthetic technician. So of course this ring, combined with his 6-foot, six-inch frame, attracted attention everywhere we went. He played on this all weekend.

We get home one night after drinking, one thing led to another, and we had sex. Afterward I left to go to my son’s room. Everything’s all good right? Wrong…..

“In honor of WVFC, I think we’ll get this piece up on the site tomorrow,” smiled Ramakrishnan. “But they have to check us out to see how it comes out.”

Submission guidelines for My Very Worst Date are here. For the contest, your stories must be 500 words or less; use the SUBMIT page or via email by February 12. The winner of the contest will be announced February 14.

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