What’s The Worst Valentine’s Date You’ve Ever Had?

What’s The Worst Valentine’s Date You’ve Ever Had?

Posted by Lady Wimbledon | 12 February 2018 | Arts & Culture, Magazine
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The closest I’ve ever come to having a Valentine is probably in ninth grade when Russel, the school’s self-confessed ‘genius’ (which should already tell you something about the kind of guy he was) sent me a red, rectangular card scribbled with three sentences of grey pencil in the most illegible ninth-grade-boy-like-handwriting you could imagine.

After staring at the one-sided, card presented to me with a heart-shaped chocolate wrapped in red glossy foil for a few minutes, I could just about make out what Russel’s attempt at wooing me was: he’d half-scribbled whatever Shakespearean quote on love he could find (I mean… good on him for going to William on matters of the heart) but for some reason which still baffles me to this day, in the age of Google, he couldn’t finish the quote and instead jumped straight to “Will you be my Valentine.” A part of 19-year-old me wishes boys were this blunt and frank when it comes to love – but surely Valentine’s Day calls for a bit more peppering of adjectives?

Anyways, long story short: He took Ashley to the ‘V-Ball’ two nights later. I guess he sent out a lot of red cards scribbled with the words of Shakespeare that year. Luckily, I can’t say that this experience has tainted February 14 for me. I don’t exactly ‘celebrate’ it either but it’s a day that I live through unproblematically each year. I can’t quite say the same thing for the bloggers I got in touch with. They make 14-year-old Russel seem smooth and suave in comparison. With that, I give you some blogger’s Valentine’s Day horror stories:

Lady Wimbledon

Some people have had one or two bad Valentine’s Days. Lady Wimbledon who is the #LADYBOSS in charge of ladywimbledon.com, told me about FOUR bad Valentine’s dates just off the top of her head. I think I triggered some bad memories… but it was done all in the name of love (or that’s what I’m going to keep telling myself).

Lady W said she has had some pretty bad V-Day’s and has the memories to remember them. She said: “My fake nails pinging in my date’s soup” was pretty bad. YIKES! That sounds like any girl’s nightmare-come-true!

Lady W then told me about a time when she had “to trawl from restaurant to restaurant trying to find a table as my boyfriend hadn’t booked.” Sometimes life happens and things get in the way but a well-planned evening is particularly enjoyed on Valentines Day.

Fancy a night in with beans on toast in shape of a heart? Because that’s exactly what came Lady W’s way on Valentine’s Day.

Are you thinking things couldn’t go any more wrong for one person? Guess again! This took the cake for me. Lady W said: “I was wearing a self-portrait jumpsuit that I couldn’t undo to go to the loo, so my date caught me asking another man to help.”  In retrospect, my brief encounter with Russel in ninth grade wasn’t all that bad.


The Wong Blog
Monica who blogs over at thewongblog.com really liked a boy (hopefully not named Russel) when she was 15-years-old but never had the courage to speak to him.
“On Valentines Day, being the shy, weird kid, the next time I got to sit to him in class, I wrote ‘[name] I like you’ in my notebook hoping he would see it. I dropped the notebook after I wrote it, smacked my head on the table and had to go home. He never saw my note.”

Ouch! That sounds like a rough Valentine’s Day to me.
Rachel On Route


Sometimes, Valentine’s Day is ruined because of issues completely unrelated to matters of the heart.

“Back in 2013 my boyfriend and I were applying for Canadian visas. During the process, I missed a question on his application about his country of residence, so it auto-filled with the first country in the alphabet, Afghanistan, instead of the UK! On Valentines Day, I was sifting through our paperwork and realised my mistake – I then had to call him and admit I’d messed up his application! It was heartbreaking, as we thought all our travel plans were ruined,” says Rachel from RachelOnRoute.

Luckily, it all worked out in the end and the couple did indeed end up visiting Canada. It was just at the cost of their Valentine’s Day.


Kay The Runaway

“I told my husband a few years ago that Valentine’s wasn’t that big of a deal to me. So last year he didn’t even acknowledge the day. I quickly realised it was a bigger deal to me than I thought,” says Kaylene from KaytheRunaway.com

I chuckled when I first read this because it sounds like Kaylene has a great listener on her hands. I have no doubt that in the years since his mishap, Kaylene’s husband has made up for it.



“Unfortunately for me, my ex was a little bit of a d**k. Anyway, it was Valentine’s and we were both at separate universities and I was desperate to spend some time together. He invited me down for a couple of evenings and I was super excited.

Valentine’s included a meal out followed by a movie which was great. Yet, he neglected to tell me it was, in fact, a group meal and movie since it was his housemate’s birthday. We ended up spending the night with his pals in the local nightclub. I got super smashed in the end since I didn’t want to be the ‘miserable cow’ he often explained me as to his mates,” says Charlotte-Nichole from charlotte-nichole.com.


Jack Deyes

“One Valentines Day me and the girl who I was going out with asked me if I’d like to go round her house and spend Valentine’s Day there and I said yes. But what I didn’t know was that on Valentine’s Day she ended up asking her ex to come round instead and the way I knew about this is because she messaged me by mistake,” says Jack Deyes who blogs over at jackdeyes.wordpress.com.

She did end up apologising, but nonetheless, Jack, it sounds like you dodged a bullet! I’m not sure what Russel is up to this Valentine’s Day, but a scribbled note popping up in the mail would be a great Valentine’s Day after seeing how bad things could really be. Hopefully, by now, his handwriting has improved to a legible scribble, at the minimum, but I guess I’ll never know. But for his future Valentine’s sake… I HOPE SO!


If you think you’ve had a Valentine’s Day worse than these above you need to tell me about it. What’s your worst Valentine’s Day experience?

Till next time – Steph
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