Crazy Valentine’s Day Stories

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On Instagram we asked our followers about their strangest stories on Valentine’s Day. We have written down the 10 best adventures for you…

Ellie, 22: Just like in the movies…

A few years ago, when I had just started dating this guy, I thought I could surprise him on Valentine’s Day by turning up at his door – in nothing but sexy lingerie and a coat (just like in the movies, right?). I obviously never told him I was coming over and when I got to his place, his parents, who I had never met before, were there. They even invited me inside! I had to stand around for a while making awkward conversation before I could make up an excuse and escape. They must have thought I was so strange – refusing to take my coat off or even sit down!

Annie, 25: A Hairy Situation

Worst Valentine’s Day ever: I was in Dubai visiting my dad and planned a surprise for my boyfriend, who was back home in South Africa. My mom helped and got all of his favorite things together for me. We made the day super special. In return, all I got from him was a picture of a hairy ball sack – in the shape of a heart. That was probably the most romantic thing that he’d ever sent me in our almost three years together… safe to say we aren’t together anymore.

Marissa, 31: A Nightmare on Valentine’s Day  

A couple years back I was alone for Valentine’s Day. So I decided to hang out with a Tinder date. He was in my city but wanted to take me to Toronto to ‘wine and dine me.’

I went to meet him at the bus station and looked around for him. All of a sudden, this guy (who basically looked like he had just left a school shooting) comes up to me and says: “Hi, are you Marissa?” “Yes,” I said, while looking him up and down. “Hi, I’m Caleb,” he replied, with his black trench coat flying in the wind. On top of the trench coat and black platforms, he had the greasiest hair I’ve ever seen. “Are you excited to go out for Valentine’s Day with me?” he asked.

“Of course,” I said.We get on the bus to go to Toronto. I legit should have left at that point. He asked me where I wanted to go for dinner. I said sushi would be okay. And he said, “I would love to eat sushi off your naked body.” He then proceeded to tell me that if I was naked, he would examine my body in front of a mirror. Also, he told me that when he was a kid, he was jumping on a trampoline. He fell off and hit his head on a trash can, and since then he was slower than the rest of the class…so I am guessing this is all making sense now.

At this point, I messaged everyone I knew in Toronto to save me from this dude. No one wasavailable. We get off the bus and he goes to get his suitcase. All of a sudden, it burst open and all of his clothing went everywhere. It was a windy and gusty day, so he was running around Bay Street, dodging cars, to get his Metallica t-shirts off the street. We went to get some sushi. Before that, I decided to find the nearest bank and take out money, in case I had to jump into a cab. I stood in front of the ATM whilst he looked right over my shoulder. I told him to back up and he said, “Yeah, but whatever is yours is mine, because we’re in a relationship.” I freaked out. I took out 60 bucks and put it in my purse. As we were walking up to Queen Street, he turned to me and said, “Is something wrong?” I said, “No, I’m just tired. It was a long drive.” “Oh, you’re tired? Well, instead of sushi we can go back to my place and you can take a nap on my bed,” he said, “but don’t worry, I won’t slit your throat in your sleep.“

I was done! I started running down Queen Street. He was chasing me, yelling, “What did I say?Did I say something wrong? Come back!” I screamed back “UHHH MY FRIEND’S MOM JUST DIED – I HAVE TO GO!” I found a cab, got in and locked it. He came to the door and screamed, “I DIDN’T DO ANYTHING WRONG!” The cab driver asked, “Where to?” and I just said, “CAB DRIVER, STEP ON IT!” – like I was a kid in a Nickelodeon film. I ended up getting about 50 texts afterwards. He said that he was sorry, but I never spoke to him again. I ended up going to a sushi bar and eating Valentine’s dinner by myself.

Joana, 26: Dinner with the parents

A guy I was dating invited me to his place for a romantic homemade dinner on Valentine’s Day. Turned out, he lives with his parents and the romantic dinner was homemade… by his mom. His parents stayed to eat with us while having an awkward conversation about me as his girlfriend…

Timothy, 25: Gone Fishin’

We had only been dating for a few months. So we decided to have a “low key” Valentine’s. We cooked, we had a bottle of wine and we planned a night with lots of sex. About 10 minutes into getting to it, I came pretty quickly, pulled out and looked down, then at my girl, in horror. The condom I was wearing was no longer there, but instead still inside her! We spent the next 15 minutes “fishing around” to try and retrieve it. Needless to say it wasn’t that romantic and the mood was officially killed…

Francesca, 18: Drawing the Short Straw

So, I was on a date with this guy and I’m pretty passionate about protecting the environment. So naturally, I asked for no straw in my cocktail. He then gave me a weird look and asked for two straws. We started discussing this. Long story short: he ended the conversation by telling me that he hates turtles and eats turtle soup for breakfast. I’m not sure if it was a joke. Of course, I ended the date there and then, and never looked back! Hopefully this year will be better…

Annie, 39: Mommy’s Little Treasure

I don’t have a V-Day story, because all of mine have been laaaaaaammmme. But my mum still sends me cards and pretends they’re not from her. I’m 39

Jackie, 44: Neighborhood Watch

An ex-boyfriend blindfolded me in his car and walked me across a car park in to the lift. Then he took me inside his apartment and sat me on a chair. After about 30 minutes he took the blindfold off and I was surrounded by flowers, balloons and candles. Then, all of a sudden… there was a knock on the door: it was the police! Someone had seen him with me and thought he’d kidnapped me. The police came in to check that I was okay. But declined to join us for dessert. Now we can laugh, but I was 19 at the time and quite embarrassed.

Brooke, 33: Puppy Love

I was visiting my girlfriend in her hometown in Norway for the first time after months of long distance dating. She’d driven us to a secluded spot by a lake. We had wine and cooked hotdogs by the fire (romantic right?). It started to get a bit chilly as the night wore on, so we retreated to the warmth of the car. Her mum’s car. Her teeny-tiny VW polo. It’s Valentine’s Day, we haven’t seen each other in months and we are alone in a confined space. It starts to rain. Things happen. Afterwards, we get ready to leave and find that the car won’t move.

While we were busy, the rain has made the ground all soggy and the car has sunk about 3-inches into the ground. It’s cold and still raining. But I’m outside the car trying to push it out of this trough. It doesn’t work. We try a few more ideas but nothing works. I then get down on my knees and start digging feverishly beside the sunken wheel. My girlfriend thinks I’ve lost my mind or I’m channeling my inner doggo. She finally gets on board with my idea to dig the wheel out of the sludge and starts helping. When we are done, one little push and the car rolls up and onto level ground. No problem. We are now soaked to the bone and covered from head to toe in mud. We can’t get into her mum’s car like that. She’d kill us. Luckily, there’s water close by. So at about 1:30 AM, two girls could be seen stripping off jeans and shirts and haphazardly washing themselves in the freezing water, before bundling themselves into a toy car in their underwear.

We drive home, sneak into the house hoping her mum/dad/sister don’t catch us in our half-naked state and make a beeline for the shower. Clothes are completely ruined. Sadly, that beautiful girl and I are no longer together, but whenever I think of that Valentine’s Day adventure (perhaps misadventure?) it still makes me smile.

Angel, 48: The Valentine’s Crashers

My craziest Valentine’s Day was almost 31 years ago. My friend had a party and a few people (who were not invited) came over. We had ran out of alcohol (we where all underage). One of the uninvited guys was the only one over 21. My friends decided one of us should go with him to make sure he doesn’t buy cheap beer with our money. I was picked by the uninvited guy.

Mr. Uninvited was driving a Camaro with tiny seats. His buddy decided to come along. No problem, right? The buddy refuses to sit in the back and Mr. Uninvited refused to allow me to sit in the back. The compromise? I sit on the buddies lap. The whole way to the liquor store Mr. Uninvited asks for a kiss.  Like literally a thousand times. We get back to the party, drink beer and wine coolers, and I decide to go home with Mr. Uninvited. We did some hanky panky and he drops me off at my friend’s house around 2am and leaves. The door is locked and I’m out in the snow with a flimsy jacket and a mini skirt. I have to bang on a neighbor’s door to allow me to use the phone to wake my drink friend.

Mr. Uninvited was really only supposed to be a one night stand. I mean how rude to drop me off and not make sure I could get inside the house? Mr. Uninvited now prefers to be called Dad and Husband. We’ve been married since 1995 and have 2 adult children!


Our author Tina thinks, Valentine’s Day is overrated. Read here, why.


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