We enjoyed our “Worst Valentine’s Date Ever” contest and all the great submissions so much, we thought we’d extend it for one more day and offer you the chance at a bonus prize- Readers Choice!
We’ve chosen 10 additional entries and we are giving you 24 hours to vote on your favorite.
The entry with the most votes, chosen by YOU will receive a $100 Stockroom Gift Certificate!
Each of the entries listed below has been titled and it’s up to you to comment on this post with the title of your favorite story.
Votes will be tallied and winner announced by 6PM PST on Feb 14th.
Thanks again to everyone that participated in the “Worst Valentine’s Ever Contest”!
Never Forget Your Trunk - WINNER!
- Everybody Loves a Teddy
- The Road Trip to Perdition
- Bit by the Love Bug
- Un-Romancing the Stone
- It’s Not Super Effective
- Pandora’s Box
- A Quaint, Rustic Getaway
- Not-So-Special Delivery
- Mistaken Identity
Expand this page to read all 10 entries!
Everybody Loves a Teddy
One of my worst Valentines Dates Ever had to be a few years ago, when my boyfriend at the time and I went out for dinner. It was one of those places where you could eat a meal and then play arcade games. It was a great night as I had driven about 8 hours to come to see him as he had recently moved to go to school in another city but in the same state. The whole night he was playing the games where you would win tickests and racking up a ton of them. Even though he had already given me a gifts, I figured that he was trying to win me something that I had my eye on since we had walked in.
The end of the night, he takes his tickets and turns them in for an over sized stuffed bear. Not really my style, until he says to me that he won’t it for his roommate who was alone that night. I spent the whole walk from the ticket area to my car, listening to women who walked by going on about how lucky I had to be to have someone win me that. And just smile gritting my teeth totally embarrassed, and not wanting to say that it was for his room mate and not me. I wanted to die, I totally get that he was being kind to his roommate, but couldn’t he have waited till a time that wasn’t our valentines day date?
The Road Trip to Perdition
My freshman year of college, I had a crush on this guy. We were each other’s best friends at college so far, which really didn’t say much…The whole first semester I had the crush, but I didn’t say anything. My good friend who introduced the two of us then let me in on a conversation they had regarding me, in which he disclosed that he would never be interested in dating me because I was not attractive, I didn’t inspire him, I wasn’t intelligent enough and I made bad friend choices. About a month later he asked me out. We went out for a couple months and had a decent relationship, at least I thought so until a couple years later when I realized that it was both very physically and emotionally abusive. Anyways, we did a lot of random little things, such as going to swing in the park, taking hikes and pictures in the snow, and watching movies while making bets who could last the longest without kissing the other. So when he decided to take a random 2 hour road trip to the beach Valentine’s morning, it wasn’t a surprise at all. Merely sweet. At least…until he broke up with me about 90 minutes into the drive, leaving me spending the rest of Valentine’s Day single…stuck with my ex.
It wasn’t a good Valentine’s Day.
Never Forget Your Trunk
So early February, we had watched this movie in which a stripper performed at a bachelorette party. He said those dreaded words, “I bet I could do that.” I looked at him, looked at the screen, looked at him, looked at the screen. “Dear…no. Dear….I love you. Just…no.” He looked over at me, “What? You don’t think I can do that?!” He was a state champion heavyweight wrestler, not exactly what you would picture when you think of a stripper. “No…dear, I don’t think you can do that.” He sighed and we finished the movie. We forgot about it.
For Valentine’s Day we had planned to go out to dinner, come back, cuddle and have a night in with each other. Ha. Was I wrong. I don’t know why, but we watched a similar movie. I had to use the bathroom. We paused the movie and I got up to go. When I came back, he’s not in the room, but there’s just an office chair in the middle of the room.. “Hey…where’d you go?” The only reply I got was a cryptic, “I have a surprise for you. Sit down.” Worried, I sat down. He opened the door, and comes out wearing an male thong, which can only be described as an elephant mask for a penis, and a bow-tie. Nothing else. I am stunned. My boyfriend of 2 and a half years. All 365 lbs of this wrestler who could NOT be a stripper….who had now decided that he was a stripper.
He starts to dance. He starts pelvic thrusting, trying to make the elephant trunk move in a circle….and succeeds in making it somewhat flop up and down. He is so concentrated on his carefully rehearsed dance moves that he has yet to notice the look on my face. He walked over to me, preparing to (I think) grind on me. I couldn’t help it. I didn’t think about it. I just put my hands up shielding myself. “Babe. This is an elephant trunk. What are you…Why?” One more look at the elephant trunk staring me in the face…and I burst out laughing.
He wasn’t amused. He still got laid. It takes some courage to strut an elephant trunk around on your dick.
Looking back on it now…there’s a reason he’s my ex. Not many people can make Valentine’s Day both terrifying and hilarious. He, somehow, managed.
Bit by the Love Bug
Finally, finally we had a babysitter for the 2 little ones and were going to escape for the weekend! Nope! Grandma got sick, so we had to cancel our reservations and of course lost most of the deposit. Still hoping for a little romance, we planned on putting the kids to bed early and have a late night candle light dessert and romance time. No such luck! As soon as the chocolate was ready, kid 1 is up puking, followed soon by the 2nd. Needless to say, spending what was suppose to be a great romantic time cleaning puke was not the plan. To add insult to injury, once the kids were doing better– I got it next!
Un-Romancing the Stone
Well without a doubt it was 1990. I was all set for an evening of romance and of course deliciously wicked sex. I had picked up a few new toys, and nice bottle of wine, and of course chocolates. My ex had sent our son to the grandparents, made dinner and picked up a video for after. All day at work I had thoughts of what the fun we were going to have that evening. Diner was excellent, we were having a great time and then she went and popped in the video into the VCR. The screen flickered and I wondered what we were about to watch, would it be a classic romance? a porn? NOOOOO it was perhaps the least romantic film I have ever seen, it was the 1989 film War of the Roses. It is a black comedy about a wealthy couple with a seemingly perfect marriage. When their marriage begins to fall apart, material possessions become the center of an outrageous and bitter divorce battle. Needless to say there was no sexy time that night. The moral of the story is never let her pick the film.
It’s Not Super Effective…
As I’m trying to write this story, I don’t know where to begin. Perhaps the best way to start this is to say that this was the day I decided to give up my virginity. We dated for months and I thought Valentine’s day would just be the perfect time. He was an über nerd, but luckily he was a nerd at a time where being nerdy started being hot. He was popular with the ladies, but he had his eyes out on fresh meat. He paid for a room downtown, in front of the light-rail. Second floor all the way in the end of the hallway. Now this wouldn’t have been any problem if I hadn’t been stopped by four different staff members asking if I was lost, being that I was a young girl wandering the halls of a hotel. It was still early in the afternoon and from what I had researched online, people suggested to have sex before dinner, and so things got hot and heavy as quickly and awkwardly as possible. At one point he had decided it was time I graduated from the missionary position on the bed and pick me up to push me up against the balcony glass door. The glass felt good on my hot body, so it took me a few seconds to realize that my naked ass is on the glass door, which is right across from the light-rail station. In a fit of panic and anger I told him that we were done. I wanted to take my shower and leave for dinner early. He did not take that as seriously as I intended; he came into the shower with me and convinced me to try again. Neither of us had experience in shower sex and within seconds, we had a slip. I grabbed onto the cheap hotel shower curtains and we both fell with the plastic covering us. Needless to say we were not in the mood anymore. I was worried that since a few rings that held the curtain broke that he would have a huge charge on his hotel bill, so we went out downtown to look for a replacement. Shower curtain rings are not something commonly found downtown, and by the time we found it, we had missed our dinner reservations, so we went to the Burgerville across the street from the hotel instead. We went back to the hotel to try again since neither of us had finished from earlier. Now I don’t know if you’ve ever read the DC Comic books about Captain Marvel, but he gets his superpowers by yelling, “Shazam!” And when he came, that’s what he exclaimed. That was the last thing I could ever expected! After a while I had to go home and do homework for school the next day. The next few years he used to send me an e-mail on Valentine’s day with just Shazam! It stopped maybe two years ago, but this memory will never go away.
So there I was, a young and inexperienced baby butch. I’d met up with her for a date to the local Ren Fair and a night of wine and movies, and we corresponded a fair bit online. I thought things seemed to be going pretty swell. Then Valentine’s Day came rolling around.
Well shoot, I’d never had a girlfriend before, and despite my insecurities and uncertainty about the exact status of this relationship, I figured I’d take a chance on this crazy idea that hit me in the wee hours of the morning. What was there to lose, right?
Now, I’m a crafty sort of critter, and handmade gifts are supposedly super special and romantic. I raided the hardware store and craft store for supplies, and in a few days I had hand-painted a basswood trinket box with knotwork and lined it with velveteen in her favorite color, and constructed a sturdy chainmail leash with a black leather handle. I coiled the leash inside the box and wrapped the whole thing in dusky rose-colored tissue paper and tied it with hemp twine. I swallowed my nerves and bundled up the package for shipping and took it to the post office.
A couple of days later, I got a package from her in the mail. It looked like the same box I’d shipped her gift in. Okay, recycling is awesome, so good on her! The contents were wrapped in white paper, tied with…the same hemp twine as…
It was the box. With the leash inside, and a note. It was probably one of the sweetest and gentlest rejections I’ve ever gotten, praising my creativity and skill, but it just wasn’t gonna work out for a myriad of sensible reasons. I wound up sending the box (sans leash) back to her with an apology for overstepping and genuine thanks for her honesty.
I was pretty crestfallen at the time, but in hindsight I can’t help but laugh at my inexperience, like that overexcited puppy who bowls you over in its enthusiasm because it doesn’t know any better just yet. I’ve learned a bit more about patience and expectations since then, thank goodness. It was a rough early lesson, but a good one to have. This lady and I have remained friends in the years since my overeager faux pas, so I’m glad for that. That leash is still a part of my personal kit, and it gets compliments just about every time I wear it. I’m also glad to say the experience hasn’t soured me on thinking up creative and kinky gifts for when Miss Right finally does come along; when the time is right, it’ll have been well worth the wait.
A Quaint, Rustic Getaway
In 2010 I thought it would be a fine idea to plan a little mini vacation for valentines day. The father of my boyfriend at the time lived with us so I started looking for a hotel room to book. Not wanting to travel far or spend much money (I was 20 at the time), I found what looked (online) like a beautiful hotel in the heart of downtown Los Angeles. Booked it.
Valentines Day afternoon we took the bus to the hotel that I paid for (can you see why he’s an EX boyfriend?) and the lobby was wonderful! Really ornate and old Hollywood looking. Then we left the lobby for our room. When we got there, maids were cleaning and sent us to another room, which were all about the size of a closet, with a view of skid row. Trying to make the best of things, I put my stuff down and suggested we find some dinner. The only thing walking distance was a hole in wall Chinese fast food place that served us questionable meat. Headed back to the hotel we dodged wandering homeless people that would lunge towards us like zombies.
A nice romantic bath will solve things! Or so I thought. There were pubes from the previous guests in the tub. Sex? Boyfriend was too stoned and dropped ashes burning holes through my favorite bra. FINE, I thought, I will just go to sleep and this will be all over…
Sleep wasn’t possible due to the meth dealer strangling a junkie in the hallway shouting for 2 hours in the middle of the night and there were blood stains on my pillowcase. Oh if I only knew it was THAT kind of hotel. I know I left out gifts, that’s because I got him a bottle of cologne from Victoria secret in special valentines day packaging and I got… The bill for this pleasurable experience.
My worst Valentine’s Day ‘event’ wasn’t actually a date. But it was the
reason I still hate Valentine’s Day to this day.
Let me explain. I was engaged to be married to a guy I had been dating
for two years. We were set to marry that June. He was a couple thousand
miles away at the time in Canada and we spent a lot of time on the phone
and exchanging letters – it was 1989, before email. A week before V-day,
I sent him a large package with a teddy bear and some cologne that I
loved. On Valentine’s day I received a small letter from him. A Dear
Yep, he ended up breaking off our engagement Valentine’s day of all
days. Sure, he didn’t know his letter would get to me on that date – at
least I hope he didn’t – but still, it created such a dislike for the
crappy day for me that today, 24 years later, I STILL hate it.
The strange thing is that by the time I was 30, I was glad he broke it
off because I was kinky and he was about as straight-laced nilla as you
Still not a fan of V-day though.
The worst Valentines day I’ve had so far is back when I was in high school and my boyfriend was in basic for the marines, so my best guy friend brought me a rose to school on Valentines and then everyone at school thought I was secretly dating him, broke up with my boyfriend for him or was cheating. My best guy friend was fat and not the most attractive, so it was a big deal.