Crazy Valentine’s Day Stories

Valentine’s Day isn’t always romantic. On the contrary: 15 people tell really crazy Valentine’s Day stories that’ll make you laugh.

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.

Joana, 26: Dinner with the parent

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…

Anna, 39: A special suprise

Don’t know if this is really crazy but for Valentine’s Day a few years ago my boyfriend drove almost three hours to come see me and I was miserable the whole time because I didn’t know how to tell him that I had realized I’m a lesbian. We broke up the next week.

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…

Sarah, 30: Not a holiday…

My craziest Valentine’s day story would be when I had a boyfriend a few years back, we were having a few issues in our relationship. So in hopes he would want to spice things up for Valentine’s day I asked him what we were doing because it was already the night before. He said, Valentine’s day is not even a legit holiday.

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.

Julia, 22: Forever… or not forever

I wouldnt call it crazy more like, sad. I was preparing to propose to my girlfriend of 2 years. It took like 4 months to plan everything. I went down on my knee like one would when proposing and her ex girlfriend saw us and came over. Turns out she was secretly dating her “aggressive” Ex and me at the same time.

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.

Katherine, 18: Relight my fire!

Oof so! One valentines day a while back I was in a tumultuous “relationship” where my ex partner gave me a big stuffed bear. I loved but then later in the day found out I was being cheated on and invited them over, lit the bear on fire in front if them in my parking lot, and then dumped them. Truly iconic, although I would have loved to have kept the bear lol.

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.

Ash, 32: Shopping with mum

Here’s my crazy valentines story. I was dating a guy in the navy and he was stationed in Great Lakes, near Gurnee, Illinois. I went to visit him on base and his mother invited herself on our day together. She insisted we go to Gurnee Mills, which is a large outlet mall. We spent the whole day wandering around the mall with his mother. To make matters worse, his gift to me was a dog tag with his face lasered onto it. He had it made in front of me at the mall, while I told him as nicely as I could that I didn’t really want it. I ended up giving the necklace to his mom.

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!

Sam, 20: Suddenly stepmother

Once my Valentines Date was a bit older then me. The Date was good, very romantic but not in a cringe way. At some point we kisst and he told me how happy he was to finally find a now mommy for his toddler an that we need to meet with his son soon. You can imagine how shocked i was haha the rest of the date was pretty awkward because I needed to explain why I don’t won’t go be a mommy for his son after a first date.