The past week we’ve heard from a lot of you, sharing your awkward tales of Valentine’s dates past and the days and nights that…didn’t quite turn out as planned.
We came together in deep discussion and mulled over the submissions to find the perfect stories that really captured that not-so-awesome feeling and after a much heated debate, the votes are in!
Ladies and gentleman, we present to you the winners for the “Worst Valentine’s Date Ever!”
A huge thank you to all the brave souls who were willing to share with us their anecdotes. We truly enjoyed reading all of them and we hope that this upcoming holiday, and every Valentine’s Day to come, is filled with very happy and very sexy memories.
- Grand Prize Gift Pack Winner –
Pitching a Tent
I have been married for years, and I love my husband, but our first Valentine’s Day takes the cake. We were young and in love and it was going to be a Valentine’s Day to remember. Our idealistic selves thought we would have more than enough love for just one day so we had plans to spread the holiday out over a few days.
We had booked a campsite by the beach for a relaxing week away. Yes, it is February and not all people are up for winter camping, but I’m no slouch when it comes to winter camping. Growing up, I was the girl that went on the Boy Scout trips with my brother and his troop.
However, it was camping in the South, so it was supposed to be in the 60s during the day, the 50s at night; a totally comfortable temperature.
Now, the day before we were slotted to leave, my husband and his best friend go out for drinks, my husband gets a little tipsy and asks his friend to drive home. Now his friend, let’s call him Bob, knows that the car is a little old and has been told every time he has been in the car not to open the driver side window. It could have been the booze or the time of night but Bob figured my husband needed some fresh air and rolled down the windows. When they got home, I found out that my husband had sobered up enough to realize the motor for the front window had finally died and that the window was stuck in the down position and was not moving. We taped a bag to the car and called it a night.
The next morning instead of getting up early and getting on the road like we were supposed to do, my husband sleeps in. In his early morning haze he tells me he wants to sleep in because we have plenty of time. This drives me crazy, but I figured, sure we have time what else could go wrong?
I shouldn’t have asked the question.
When my husband finally got up, in the afternoon, mind you, he called his father and they spent four hours trying to fix the window. At that point I’m a little antsy because we have several hours on the road and still have to set up the tent. My father-in-law generously offers to lend us his truck: it has wheels and will get us where we need to go (it has no radio). We put all of our things into the back bed of the truck and hit the road.
My husband and I enjoy taking road trips together, but as soon as we hit the interstate I’m out like a light. I wake up after 8PM as we are almost to the campground. We set up our big six person tent, for the two of us. I put a tarp up over the tent as they are expecting a little rain over the next few days and then try to start a fire. This might have all been very romantic if the wind wasn’t gusting and blowing out the attempts at starting a fire. Instead of a warm fire to snuggle up in front and warming up our freeze dried dinner, we had to use cold water in our freeze dried dinner. And let me tell you cold water is NOT good in freeze dried food, it gets the job done but the taste leaves A LOT to be desired. We decided that if the wind was going to keep us from cooking over a fire the next day we would go out and get a camp stove to make life a little easier. With that we called it a night so we could get back on the road early in the morning and get into town for better supplies.
We get up early and drive into town to head to the local big box store. I sent him in to get a few necessities we forgot, condoms, as well the camp stove. I know I should have expected something was up when my husband came out of the store with a smirk on his face but he got in the car gave me a kiss and handed me a cactus.
To be clear, I have one request for Valentine’s Day as well as my birthday, flowers. For whatever reason, he thinks that flowers are supposed to be a surprise, so instead of getting me what I ask for he gets me a cactus. I ask “Why a cactus, why not flowers?”, and Mr. Sensitivity says that I shouldn’t be able to kill the cactus. I sigh heavily; when a girl wants flowers for Valentine’s Day she wants flowers.
My husband had thoughtfully found an art house theater, in the area that was playing a foreign film. The movie was billed as a love story about a two people from Hong Kong that moved to the US to go to school, that was heartwarming and quirky. The movie was “supposedly” a Chinese love story, I say supposedly because it was awful. At this point all I can remember is it was about Communist in bell bottoms and abortions, it was awful and not a heartwarming love story in the slightest. We were in the theater on a Valentine’s Day date and after about an hour of this horrible movie we were bound and determined to make the best of the situation. We started making out in the theater but the talk of abortions in the background was just too much. I suggested we leave and my husband agreed. We made it back to the campsite just in time to miss the sunset over the water, but we were not to be deterred. We were going to have a sexy romantic Valentine’s Day if it killed us, I mean we didn’t get those condoms for nothing. I do a sexy strip tease for my husband that ends with me gingerly tearing open the condom and rolling it down over his penis.
Fast forward not even 5 thrusts later and I hear “Oh, no”. Immediately my mind goes to the talk of abortions in the movie, did he come and the condom rip? To my relief and just a little horror, no, the condom had just come off. Apparently the brand was not his usual but instead of coming off nicely or realizing what had happened it came off inside me with one thrust and the next seemed to get it solidly logged somewhere near my cervix. This lead to what we now lovingly refer to as the “condom fishing game”. Both he and I proceeded to try and find the condom and get it out of my vagina for what seemed like hours, but was probably no more than a few minutes. At this point we didn’t have the mental willpower to want to continue so we called it a night.
The next morning was our last full day of our Valentines vacation, we got up early and cuddled as we listened to water droplets bounce off the tent. As it was getting cold outside we took the campstove into the tent to cook breakfast, no sooner than we finished cooking did we hear the water droplets go from little splats of water to little thuds of ice.
Sure it was cold but we had full plates and hoped to have full bellies but that was not to be the case. The winds picked up and started to buffet the tent, then without warning crack a tent pole snapped and the tent collapsed on our heads. We tossed on our jackets over our PJs and tried to get things together and put them in the truck. With the bitter cold temperatures and the gale force winds we gave up and just lifted the tent as a whole into the back of the truck. My husband tried to get the tarp I tied up down but with the wind and cold his fingers just could not undo the knots, eventually with a little help from me we got it down and into the bed of the truck. We piled into the cab turned the heat on high and looked at each other trying to figure out what to do next.
We still had another day at the campsite but now we had no tent and the wintery mix was starting to stick to the ground. I had family that lived close enough that we could get to them within an hour so we made the call that going to spend the last romantic day with family was better than staying at the campsite.
Upon arriving we were stripped out of our cold wet clothes and given warm blankets and tubs of warm water to soak our extremities in. We were thankful for the warmth. By the afternoon the temperature had completely shifted and the ground had melted and the birds were out and chirping, tweeting about how the day was beautiful almost rubbing in the fact that without the tent we couldn’t enjoy camping. It was now about 70 degrees and beautiful.
I felt bad that we didn’t have a smooth Valentine’s Day vacation and our last night was going to be spent on the pull out couch at my family’s home. I wanted to do something nice, something I though my husband would love. I knew I could make fettuccine alfredo: he loves it, I love it, what could go wrong?
I put the noodles on the stove and started on the sauce. Just when I thought we were on a clear path, the top to the garlic powder fell off dumping the entire contents of the jar into the pan. I tried to get out as much as I could but the sauce just soaked it up. The sauce still smelled good and we are both big garlic fans. I thought I might have salvaged it enough for it to be palatable, and it was palatable if not a bit garlicky.
OH, the unintended consequence. We could find each other in the dark for days after we reeked of garlic that much. The family even commented that they thought we had spilled garlic in the living room it was so strong oozing out of our pores.
We went home the next day more frazzled than when we left, it wasn’t the romantic getaway that we had planned. It was an unmitigated disaster. The only upside is that we are still together and with time, a lot of time, we have come to laugh at just how awful that memorable Valentine’s was.
- 2nd Place $50 Gift Certificate Winner –
The Show Must Go On
This doubles as not only my worst Valentine’s, but also the worst date I’ve EVER been on.
My boyfriend’s uncle was playing a background part in a local production of the opera Carmen. Kenny told me that he had free tickets because of it and wanted to take me for Valentine’s. I got so excited because I love the opera and had always wanted to go to a live show and thought it would be great for a VDay date. I was proven incredibly wrong.
Here I am, dressed to kill, waiting to be picked up. It’s not his car that picks me up. It’s his aunt, with him in the passenger seat. I asked about dinner and was told that both of them had already eaten, so there were no plans to eat at all. We got to the venue, where he takes me to the ticket counter and tells me that I had to purchase my own ticket. I asked about the free tickets he said he had. “Oh, yeah. We got two free tickets, one for me and the other for my aunt. I never had a third one for you.” I didn’t have the money to buy my own ticket. When I explained this to him, his response was the most embarrassing thing I think anyone could do. He started panhandling to complete strangers to get me a ticket. I couldn’t believe it. He somehow was able to gather up the money to buy me the ticket, but every part of me didn’t want to stay there. Anyway, so the show starts, and i’m in the most amazing seat, except that I’m nowhere near the boyfriend and the aunt. I was however, dead center on the bottom floor, right about in the middle of the rows. Not too far forward or too far backwards. Just perfect. However, I decided that it would be more appropriate though, if I were sitting with my own company. So after intermission, I went to sit with them…only to find that I was at the very back of the right wing and could barely see a thing. “free tickets for family” apparently meant all the seats they knew they’d never fill. The worst part of everything was afterwards, when I confronted him about how terrible the night was, he didn’t see how he’d done anything wrong.
- 3rd Place $25 Gift Certificate Winner –
My worst valentines day was three years ago. My boyfriend at the time invited me over for what I thought was a romantic evening. When I got there, I discovered he had also invited a close gal friend of ours. This girl also happened to be a school crush of his back in the day. We had a few drinks, and started playing a game called what the f*ck (a question game where you have to choose your most desired result of some very off the wall scenario). It was halfway through the scenario, the question was ‘would you still have sex with your high school crush, even if you were with someone at the time’. He looked her dead in the face, and said yes. She stared at him, clearly appauled, then looked at me with a look of fear and apology. After a few moments of awkward silence, I got up, dumped both my drink and my ashtray in his lap, flicked him off, and stormed out. I made sure to drop and crush the box of chocolates he had bought me into his creme colored carpet too. Our gal friend texted me 20 mins later, asked if she could come over and talk. When she showed up apologizing and in tears, she proceeded to tell me that I hadn’t even left his driveway, and he had tried to kiss her. Smart move wise guy. Needless to say, neither of us talked to him again.
So a few years ago my now fiance and I decided to try BDSM. For valentine’s day. I spent weeks saving up money to buy some semi decent gear. We had the basics like silk ties but I just never did enjoy light bondage. I remember specifically buying an under the bed restraint system because we could easily set it up in a hotel room during our limited time together. There were a few other things like a small crop and collar that were basic and cheap but for a college student they cost a small fortune.
Well Valentine’s day rolls around and I get in my little car to drive the hour and a half to see him. I buy the hotel room for the day and set up everything before going to pick him up for a romantic lunch. At this point everything is pretty much going as planned. Then suddenly it wasn’t.
Between me calling to say I had reached town and actually arriving at his dorm he had gotten another phone call. His grandfather had passed away. We spent the day curled up on a couch. A hotel room full of bondage gear he never got to see. It was great that I was there to console him, but truly, it was a terrible way to spend Valentine’s day.
The worst part? Going back to the tiny hotel and packing up all the gear back in my bag and turning the keycard in early and telling the owner that the room didn’t even need to be cleaned. I don’t remember what I told her but I think she assumed I had been stood up. The next time we went back to the hotel she was thrilled to see we had “made up” and gave us the room at a ridiculous discount. The gear we had saved up so much money for went to my best friend. We just couldn’t look at it or use it without being reminded of that Valentine’s day. She still uses the under the bed restraint system. One day we will have to get around to purchasing another one, to actually use this time around.