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Valentine’s Day horror stories: The bad, the ugly and the plain old scary

There’s a reason why single women (and men, for that matter) get all worked up about Valentine’s Day being a “Hallmark holiday.”

Sad woman on Valentine's Day

The anticipation that builds up before Valentine’s Day is admittedly out of control. Local Duane Reade, CVS and Walgreens stores break out the hearts, balloons, teddy bears, chocolates and obscene amounts of pinks and reds as early as mid-January.

As a (non-practicing) Jew, I often think about the single people being exposed to all of this in the same way I think about myself (and other Jews) around Christmas time. It’s just.way.too.MUCH.

Not every woman (or man) can handle the barrage of all-things love, especially when they’re single or have bad memories attached to the date. We asked our readers to tell us about their worst Valentine’s Day. Here are their stories!

Wishy-washy date

“When I was growing up, my friends and I used to love to go to this car wash near where we lived. We’d put quarters in the machine and put the washing gun on all kinds of settings and chase each other around the cars. It was a weird happening, but there wasn’t much going on in our Western Pennsylvania suburb. One Valentine’s Day in high school, my friend and I thought it’d be a good idea to take our girlfriends to the car wash as a surprise.

We envisioned this movie-type moment where they would be touched that we shared something from our childhood with them and the best things in life aren’t fancy dinners, but the memories we share with loved ones… Well, we were wrong. The girls were dressed up and excited about what we had planned, as we refused to leak any information. When we pulled into the car wash that night, they thought we were kidding and didn’t get out of the car. Needless to say, those relationships didn’t last much longer.” — Ron Plancone

Hike from hell

“I’m not the biggest fan of Valentine’s Day to begin with. It means more to me for my man to bring me flowers on a random Monday, than on a day the calendar tells him to do so. One Valentine’s Day, this guy took me (and my dog!) hiking along the Hudson River. It was actually quite perfect and we had so much fun.

Sometime later, I come to find out that he was actually dating someone else and had never told me. Way to ruin a perfectly nice Valentine’s Day. Clearly, the nice outing did nothing to change my feelings about the holiday.” — Michelle Maskaly

Friends with benefits?

“I once saved all my money to fly from Los Angeles to Vancouver to see a man I was in love with. On the plane, I brought with me a boom box, a CD mix with all romantic songs on it, candles and incense. Once I got to Vancouver, I set up the hotel room in a beautiful way with all of the things I brought. The man then showed up two hours late with another woman!

He later told me he thought we were ‘just friends with benefits.’ All this, after 10 years of being lovers off and on. It was the worst Valentine’s Day of my life. I spent it in the bathroom of my hotel room crying. I couldn’t get back on that plane to LA fast enough. To this day, I refuse to go to Vancouver.” — Jen Bosworth

Breakup blues

“In 2005, I had my first official boyfriend. I was 18 at the time, and I remember being giddy each and every time I was around Teddy. When my phone would ring and I’d see his name on the caller ID, my heart would flutter and I’d feel butterflies in my stomach. I know how cheesy this sounds, but I was just head over heels.

That Valentine’s Day would be our sixth month together. I don’t know if it’s because I was caught up in the puppy love or what, but I had high expectations for the holiday. Turns out, Teddy had other plans. Instead of flowers, chocolates or even a card, he broke up with me the day before! There was no explanation or anything — just that he wasn’t interested in me anymore. That really stung… I’ll never forget it.” — Carolina Stewart

Cheaters and chocolates

“I’m not really big on Valentine’s Day. As a man, I find it really annoying to keep up with the hype of it all — the flowers, the candy, jewelry, expensive dinners, etc. However, one year, I was straight up obsessed with this girl, Cara. I would have done anything for her. I followed her around like a puppy and to be honest, even admitting this is embarrassing. She seemed to reciprocate those feelings for me for the nine months we were together.

Around Valentine’s Day, I did tell her that I wasn’t really ‘that guy’ and wanted to know if it would be OK to do something low key instead. She was disappointed, and I kind of felt bad. So that Valentine’s Day, I decided to drop by and surprise her with flowers and all that sweet stuff. When I showed up at her place, she was on the coach MAKING OUT with some guy! Yea, Happy Valentine’s Day to me.” — Richard Bovinar

Watch: How to make a Styrofoam heart bouquet

Danny Seo shows you a fun twist on your standard bouquet of flowers.

More about love and dating

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4 Signs your Prince Charming is a fake

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